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Cas Database

112-39-0

112-39-0

Identification

Synonyms:Palmiticacid, methyl ester (6CI,8CI);Emery 2216;Metholene 2216;Methyl hexadecanoate;Methyl n-hexadecanoate;Methyl palmitate;NSC 4197;Pastell M 16;Uniphat A60;n-Hexadecanoic acid methyl ester;

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Safety information and MSDS view more

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Absorption, Distribution and ExcretionRETENTION & DISTRIBUTION OF (14)-CARBON ACTIVITY IN TISSUE LIPIDS AND FATTY ACIDS WERE DETERMINED 2 DAYS AFTER ADMIN OF (14)C-LABELED PALMITATE METHYL ESTER BY STOMACH TUBE. RETENTION WAS LOW IN YOUNG RATS WITHOUT ADIPOSE TISSUE. RETENTION IN THE BRAIN WAS FOUND AFTER 17 DAYS. THE HIGHEST LEVEL OF ACTIVITY WAS FOUND IN THE CARCASS.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
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  • Manufacture/Brand:Tocris
  • Product Description:C16 ≥98%(HPLC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Methyl Palmitate >97.0%(GC)
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  • Manufacture/Brand:TCI Chemical
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  • Manufacture/Brand:Sigma-Aldrich
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Methyl palmitate ≥97%
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 191 Articles be found

A new oxo-sterol derivative from the rhizomes of Costus speciosus

Kumar, Ashish,Chand, Gopi,Agnihotri, Vijai K.

, p. 18 - 22 (2018)

Chemical investigation of the rhizomes of Costus speciosus led to the isolation of a new compound, 22-ketocholesteryl palmitate (1) along with four known compounds, 24-methylenecycloartanol (2), cycloartanol (3), stigmasterol (4) and linoleic acid (5). The structure of new compound was characterised by extensive 1D-, 2D-NMR and mass spectrometry (GC-MS and HR-ESI-MS) techniques.

The major zeaxanthin dipalmitate derivatives from wolfberry

Long, Jia-Tang,Fan, Hong-Xia,Zhou, Zheng-Qun,Sun, Wan-Yang,Li, Qing-Wen,Wang, Ying,Ma, Min,Gao, Hao,Zhi, Hui

, p. 746 - 753 (2020)

Zeaxanthin dipalmitate (3) and two zeaxanthin dipalmitate derivatives, including one new compound (1), were obtained from wolfberry [the fruit of Lycium barbarum L. (Solanaceae)]. Their structures were unambiguously elucidated by spectroscopic analyses. Compound 2 is isolated from the genus Lycium for the first time, and its 1D/2D NMR data are firstly reported. All the compounds belong to carotenoids which are a kind of major bioactive constituents in wolfberry and are also responsible for wolfberry’s red color.

Efficient conversion of triacylglycerols and fatty acids to biodiesel in a microwave reactor using metal triflate catalysts

Socha, Aaron M.,Sello, Jason K.

, p. 4753 - 4756 (2010)

We report that catalytic quantities of the Lewis acidic metal catalysts scandium triflate and bismuth triflate promote conversion of oleic, linoleic, palmitic and myristic acids and their glyceryl triesters to the corresponding methyl esters (biodiesel) in greater than 90% yield upon microwave heating. Additionally, both catalysts could be recovered and reused in esterification reactions at least six times.

Magnetically separable porous carbon nanospheres as solid acid catalysts

Chang, Binbin,Tian, Yanlong,Shi, Weiwei,Liu, Jiyang,Xi, Fengna,Dong, Xiaoping

, p. 20999 - 21006 (2013)

A novel solid acid material, magnetically separable and SO 3H-functionalized porous carbon nanosphere, was facilely synthesized by a simple activation route. The SiO2 layer protected the magnetic core from dissolving during the process of activation with ZnCl2, and retained the highly magnetic property. The obtained materials were characterized by N2 adsorption-desorption technology and transmission electron microscopy, and the results indicated that this solid acid material possessed an excellent spherical morphology and a superior porosity with high surface area and large pore volume. The results of X-ray diffraction, fourier transform infrared spectra and energy dispersive X-ray spectra demonstrated the preservation of the magnetic core and the successful modification of -SO 3H functional groups. The solid acid activated at a low temperature (400 °C) showed the highest acidity of 1.98 mmol H+ g -1, which was estimated by an indirect titration method. The high surface area, large pore volume and high acidity endued this solid acid material excellent catalytic performance for esterification and transesterification reaction. Besides, the solid acid catalyst possessed remarkable stability and recycling property. The Royal Society of Chemistry 2013.

A rapid and sensitive profiling of free fatty acids using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) after chemical derivatization

Mok, Hyuck Jun,Lee, Jae Won,Bandu, Raju,Kang, Hong Seok,Kim, Kyun-Hwan,Kim, Kwang Pyo

, p. 32130 - 32139 (2016)

Free fatty acids (FFAs) have diverse roles in cellular energy and signaling and they are critical molecules in various biological states. Due to the poor ionization efficiency of FFAs under electrospray ionization mass spectrometry (ESI-MS) conditions, it is a challenging aspect to construct a robust platform for profiling of various FFAs in biological samples using liquid chromatography ESI-MS. In the present study, we applied trimethylsilyldiazomethane (TMSD) derivatization to improve ionization efficiencies in the profiling of FFAs. Multiple reaction monitoring (MRM) was used for the selective quantification of methylated FFAs. The optimal TMSD methylation was validated for a reliable FFA profiling. Furthermore, the high-throughput analysis of FFAs was successfully performed in short analysis and derivatization times. To verify the utility and effectiveness of the developed method, we compared both methylation and nonmethylation (intact FFA) data in the profiling of FFAs in mice liver and plasma. It is noteworthy that the methylation derivatization provided better results in FFA profiling. Further, we performed statistical data analysis where HBV and mock mice tissues were discriminated when the methylated FFAs data were used. In the lipidomics field, the present method can also be applied for the profiling of FFAs in biological samples for biomarker discovery. The present validated LC/ESI-MS/MS assay method may also be used for FFA profiling modeling studies in other biomedical samples.

Catalytic esterification of fatty acids using solid acid catalysts generated from biochar and activated carbon

Kastner, James R.,Miller, Joby,Geller, Daniel P.,Locklin, Jason,Keith, Lawrence H.,Johnson, Tyson

, p. 122 - 132 (2012)

Reusable, solid acid carbon supported catalysts were generated from biomass by pyrolysis (400-500 °C) to generate a soft to hard carbon backbone (i.e., biochar) for addition of acidic functional groups. Acid catalysts were synthesized by sulfonating the biochar and wood derived activated carbon using concentrated H2SO4 at 100, 150 and 200 °C (12 h) and gaseous SO3 (23 °C). Attenuated Total Reflectance, sulfur, and NH3-TPD analysis of the sulfonated carbons indicated the presence of -SO3H groups on the 100 °C sulfonated biochar and activated carbon (AC), with higher active site densities (SO3H density) for the SO3 sulfonated material. The sulfonated carbons were tested for their ability to esterify free fatty acids with methanol in blends with vegetable oil and animal fat (5-15 wt.% FFA). Esterification of the fatty acids was typically complete (~90-100% conversion) within 30-60 min at 55-60 °C (large methanol excess), but decreased with lower methanol to oil ratios using the biochar catalysts (e.g., 70%, 6 h, 20:1). Solid acid catalysts derived from wood based activated carbon had significantly higher activity compared to the biochar derived catalysts (e.g., 97%, 6 h, 6:1). Of the synthesized biochar catalysts, 400 °C pyrolyzedpine chip biochar, sulfonated at 100 °C, resulted in the highest reaction rate and lowest reduction in conversion (or deactivation) when reused multiple times. Drying the biochar catalysts for 1 h at 125 °C between uses maintained esterification activity, allowing the catalysts to be reused up to 7 cycles. For the SO3 sulfonated AC catalyst, such a regeneration step was not required, as the fractional conversion of palmitic and stearic acid (5% FFA, 10:1, 3 h) remained >90% after 6 cycles.

4-Amino-3-pentadecyl-3H-1,2,4-triazole-3-thiones and 3-pentadecyl-1,3,4-oxadiazole-2(3H)-thione for the preparation of dimeric palladium(II) complexes and their applications in Tsuji–Trost and Mizoroki–Heck reactions

Chehrouri, Manel,Othman, Adil A.,Jiménez-Cecilia, Samuel,Moreno-Cabrerizo, Cristina,Sansano, José M.

, p. 1301 - 1307 (2019)

The synthesis of palladium complexes derived from 4-amino-3-pentadecyl-3H-1,2,4-triazole-3-thiones and 3-pentadecyl-1,3,4-oxadiazole-2(3H)-thiones are reported. They were obtained from palladium acetate and dipotassium tetrachloropalladate(II) and their composition was assigned by elemental analysis (solid state). The resulting metallic entities were also characterized in solution based in mass spectrometry experiments. Their application in organic synthesis as cross-coupling reaction catalysts is described. One example of both conventional Tsuji–Trost and Mizoroki–Heck reactions were efficiently carried out in very high chemical yield.

Potassium 2-methoxy-4-vinylphenolate: A novel hit exhibiting quorum-sensing inhibition in: Pseudomonas aeruginosa via LasIR/RhlIR circuitry

Shah, Mayank D.,Kharkar, Prashant S.,Sahu, Niteshkumar U.,Peerzada, Zoya,Desai, Krutika B.

, p. 40228 - 40239 (2019)

The emergence of multidrug-resistant (MDR) bacterial strains in the last decade is astonishingly alarming. Many of the widely used antibiotics have failed to exhibit clinical efficacy against such strains. Eventually we will exhaust all the resources in our antibiotic armamentarium. As a need of the hour, novel strategies are desperately required not only to curb, but also to reverse, the development of resistance in these pathogens, thereby maintaining their sensitivity towards current antibiotics. Intervention of bacterial virulence, rather than killing them, by inhibiting specific pathways/targets has emerged as a novel approach to tackle the drug resistance problem. The bacterial virulence is regulated via quorum-sensing, a cell-cell communication process precisely controlled by autoinducer molecules such as acyl homoserine lactone (AHL). The present study aimed at identifying promising quorum-sensing inhibitors in Pseudomonas aeruginosa, an opportunistic human pathogen especially associated with nosocomial infections, yielding four potential hits. Out of these, potassium 2-methoxy-4-vinylphenolate was the most potent quorum-sensing inhibitor targeting P. aeruginosa LasIR/RhlIR circuitry. It also inhibited biofilm formation, various virulence factors like LasA protease, LasB elastase and pyocyanin, and motility of bacteria like swarming and twitching.

Biodiesel production by acid catalysis with heteropolyacids supported on activated carbon fibers

Alca?iz-Monge, Juan,Trautwein, Guido,Marco-Lozar, Juan Pablo

, p. 432 - 441 (2013)

Different catalysts, based on heteropolyacids supported on activated carbon fibers, have been prepared for palmitic acid esterification reaction. The influence of the catalyst (heteropolyacid) and the support on the catalytic activity have been analyzed. The results prove that an adequate combination of both is required to achieve the most suitable catalysts. Regarding to the heteropolyacid, phosphomolybdic acid seems to be the most suitable appropriate taking into account its lowest leaching. About the support, it must show an optimum microporosity, which must be wide enough to allow the entrance and exit of the reagents and products but not too wide in order to avoid the leaching of the catalyst. In addition, both decreasing of the catalytic activity and its recovery over several cycles have been analyzed.

A solvent-free, one-step synthesis of sulfonic acid group-functionalized mesoporous organosilica with ultra-high acid concentrations and excellent catalytic activities

Wu, Qin,Liu, Fujian,Yi, Xianfeng,Zou, Yongcun,Jiang, Lilong

, p. 1020 - 1030 (2018)

We demonstrate herein a novel solvent-free technique for the synthesis of sulfonic acid group-functionalized mesoporous organosilica, which was achieved from the self-assembly of a block copolymer template using mercaptopropyltrimethoxysilane (MPTS) and tetramethoxysilane (TMOS) under melting conditions without using additional solvents and subsequent condensation at high temperature (up to 140 °C). The resultant samples were designated as SMS-xs, where x stands for molar ratio of MPTS/(MPTS + TMOS). SMS-xs have relatively large BET surface areas, highly cross-linked frameworks, and abundant and uniform mesopores with wormhole-like characteristics. Interestingly, MPTS could be used as the solo precursor to prepare mesoporous organosilica (SMS-1.0), which had controllable acidity and an ultra-high concentration of sulfur (5.51 mmol g-1, the highest acid density to date), which was even higher than those of commercial Amberlyst 15 (4.7 mmol g-1), HS-JLU-20-0.8 (4.61 mmol g-1) and sulfonated carbon (CH0.30O0.33S0.16, 4.90 mmol g-1). These structural characteristics give SMS-xs excellent activities and good reusability in biomass conversions and fine chemicals synthesis, which are much better than various solid acids, such as Amberlyst 15, H-form USY zeolite, and sulfonic acid group-functionalized ordered mesoporous silica.

Super-Hydrophobic, Stable, and Swelling Nanoporous Solid Strong Acid

Wu, Qin,Peng, Jinjun,Kong, Weiping,Zou, Yongcun

, p. 816 - 824 (2017)

Super-hydrophobic solid strong acid with superior thermal stability and unique swelling properties has been synthesized by sulfonation of nanoporous polydivinylbenzene (PDVB) with super-acid of trifluoromethanesulfonic acid (TFMSA). The resultant PDVB–HOSO2CF3 has a well developed system of nanopores, superhydrophobic surface character and strong acid sites, and could be used as a highly efficient solid acid for catalyzing production of biodiesel and fine chemicals via transesterification, esterification and acylation. In terms of activity PDVB–HOSO2CF3 is superior to various solid acids such as SBA-15-SO3CF3, Nafion, Amberlyst 15, SBA-15-Ar-SO3H and H form USY. The preparation of PDVB–HOSO2CF3 offers the way to develop new kind of porous solid acid with strong acid strength and regulated wettability.

Can surface energy measurements predict the impact of catalyst hydrophobicity upon fatty acid esterification over sulfonic acid functionalised periodic mesoporous organosilicas?

Pirez, Cyril,Lee, Adam F.,Jones, Christopher,Wilson, Karen

, p. 167 - 173 (2014)

Sulfonic acid functionalised periodic mesoporous organosilicas (PrSO 3H-PMOs) with tunable hydrophobicity were synthesised via a surfactant-templating route, and characterised by porosimetry, TEM, XRD, XPS, inverse gas chromatography (IGC) and ammonia pulse chemisorption. IGC reveals that incorporation of ethyl or benzyl moieties into a mesoporous SBA-15 silica framework significantly increases the non-specific dispersive surface energy of adsorption for alkane adsorption, while decreasing the free energy of adsorption of methanol, reflecting increased surface hydrophobicity. The non-specific dispersive surface energy of adsorption of PMO-SO3H materials is strongly correlated with their activity towards palmitic acid esterification with methanol, demonstrating the power of IGC as an analytical tool for identifying promising solid acid catalysts for the esterification of free fatty acids. A new parameter -ΔGNP-PC, defined as the per carbon difference in Gibbs free energy of adsorption between alkane and polar probe molecules, provides a simple predictor of surface hydrophobicity and corresponding catalyst activity in fatty acid esterification.

Decoration of chitosan microspheres with Br?nsted heteropolyacids and Lewis ion Ti: Trifunctional catalysts for esterification to biodiesel

Tong, Tong,Li, Yiming,Hou, Rui,Wang, Xiaohong,Wang, Shengtian

, p. 42422 - 42429 (2017)

H3PW12O40 is a commonly used Br?nsted acid catalyst in esterification and transesterification reactions to produce biodiesel, whose homogeneous form and single acid sites lead to difficulties in separation and relatively less activity. Herein, the water-insoluble and multifunctional active sites based on H3PW12O40, chitosan and Ti4+ had been fabricated giving H3PW12O40/Ti/chitosan tri-functional hybrids. Such hybrids exhibited higher activity in esterification reactions due to the existence of Br?nsted acid from H3PW12O40, Lewis acid from Ti4+, and base sites from the -NH2 group of chitosan, and all also due to the generation of pores in chitosan through introduction of the Ti ions. Furthermore, H3PW12O40/Ti/chitosan acted as heterogeneous catalysts and could be separated for reuse at least six times without significant loss of activity and with little leaching of Ti4+ and H3PW12O40 from the support chitosan.

Identification of new diterpene esters from green Arabica coffee beans, and their platelet aggregation accelerating activities

Wang, Xia,Meng, QianQian,Peng, XingRong,Hu, GuiLin,Qiu, MingHua

, p. 251 - 257 (2018)

Eight new ent-kaurane diterpene fatty acid esters, namely caffarolides A–H (1–8), were isolated from green beans of Coffea arabica. Their chemical structures were confirmed by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1

Clean synthesis of biodiesel over solid acid catalysts of sulfonated mesopolymers

Fang, Lin,Xing, Rong,Wu, Haihong,Li, Xiaohong,Liu, Yueming,Wu, Peng

, p. 1481 - 1486 (2010)

FDU-15-SO3H, a solid acid material prepared from the sulfonation of FDU-15 mesoporous polymer, has been demonstrated to serve as an efficient catalyst in the esterification of palmitic acid with methanol as well as in the transesterification of fatty acid-edible oil mixture. FDU-15-SO3H achieved an acid conversion of 99.0% when the esterification was carried out at 343 K with a methanol/palmitic acid molar ratio of 6:1 and 5 wt% catalyst loading. It was capable of giving 99.0% yield of fatty acid methyl esters (FAME) when the transesterification of soybean oil was performed at 413 K and the methanol/oil weight ratio of 1:1. FDU-15-SO3H was further applied to the transesterification/esterification of the oil mixtures with a varying ratio of soybean oil to palmitic acid, which simulated the feedstock with a high content of free fatty acids. The yield of FAME reached 95% for the oil mixtures containing 30 wt% palmitic acid. This indicated the sulfonated mesopolymer was a potential catalyst for clean synthesis of fuel alternative of biodiesel from the waste oil without further purification.

THE STEROIDS AND FATTY ACIDS OF THE BASIDIOMYCETE SCLERODERMA POLYRHIZUM

Gonzales, Antonio G.,Barrera, Jaime Bermejo,Marante, Francisco J. Toledo

, p. 1049 - 1050 (1983)

Key Word Index - Scleroderma polyrhizum; Basidiomycete; sterols; fatty acids; ergosta-4,6,8(14),22-tetraene-3-one; 5α,8α-epidioxyergosta-6,22-dien-3β-ol; palmitic acid, oleic acid. The fruit bodies of the Basidiomycete polyrhizum have been shown to contain the steroids ergosta-4,6,8(14),22-tetraen-3-one and 5α,8α-epidioxyergosta-6,22-dien-3β-ol and also palmitic and oleic acids.

Template-free synthesis of porous carbonaceous solid acids with controllable acid sites and their excellent activity for catalyzing the synthesis of biofuels and fine chemicals

Liu, Fujian,Li, Bojie,Liu, Chen,Kong, Weiping,Yi, Xianfeng,Zheng, Anmin,Qi, Chenze

, p. 2995 - 3007 (2016)

N rich porous carbon based solid acids (NPC-[CxN][X]) have been successfully synthesized by treatment of N rich porous carbon (NPC) with various quaternary ammoniation reagents such as iodomethane, 1,3-propane sultone, and 1,4-butanesultone, and ion exchange with various strong acids such as HSO3CF3, H2SO4, H3PW12O40, HBF4etc. The NPC support was synthesized by carbonization of KOH-activated polypyrrole without using additional templates. Various characterizations showed that NPC-[CxN][X] possesses abundant nanopores, large Brunauer-Emmett-Teller surface areas, good stability, and strong and controllable acid sites with Br?nsted characteristics. The immobilized acidic groups were homogeneously dispersed into NPC-[CxN][X]. Notably, NPC-[CxN][X] acted as efficient, reusable and generalized solid acids, which showed excellent activity in various acid-catalyzed reactions such as esterification and transesterification in the synthesis of biodiesel, dehydration of fructose into 5-hydroxymethylfurfural, depolymerization of crystalline cellulose into sugars, and condensation of phenol with acetone in the synthesis of bisphenol A, much higher than that of various solid acids such as Amberlyst 15, H-ZSM-5, H-USY, and sulfonic group functionalized ordered mesoporous silicas. The preparation of NPC-[CxN][X] leads to the development of porous carbon based solid acids with controllable structural characteristics and excellent catalytic activity.

The Structure of Wightianone, the Pigment of a Clathrate from Calophyllum wightianum

Dean, Francis M.,Khan, Hafizzullah,Minhaj, Najme,Prakash, Satya,Zaman, Asif

, p. 1755 - 1759 (1984)

From the heartwood of Calophyllum wightianum T.Anders has been isolated, in small quantities, a clathrate composed of four molecules of a pigment, wightianone, to one of palmitic acid.Other fatty acids are present in small amounts.Wightianone is shown to be identical with zeyloxanthonone and to have the structure (1) .The isomeric structure (2) for the pigment was rejected on the basis of the aromatic solvent-induced shifts and because of biosynthetic considerations, i.e., the occurrence of gem-dialkylation in resorcinol and phloroglucinol but not in quinol nuclei.

Developing two-dimensional solid superacids with enhanced mass transport, extremely high acid strength and superior catalytic performance

Liu, Fujian,Yi, Xianfeng,Chen, Wei,Liu, Zhiqiang,Qi, Chen-Ze,Song, Yu-Fei,Zheng, Anmin

, p. 5875 - 5883 (2019)

Solid acids have been widely used as heterogeneous catalysts in developing green and sustainable chemistry. However, it remains a challenge to improve the mass transport properties and acid strength of solid acids simultaneously. Herein, we report a class of two dimensional (2D) layered hybrid solid acids with outstanding mass transfer and extremely high acid strength by incorporating sulfonated polymers in-between montmorillonite layers. The 2D layered structure and broad distribution of pore sizes allow for highly efficient mass transport of substrate molecules into and out of the solid acids. The acid strength of these solid acids was found to be stronger than that of 100% H2SO4, H3PW12O40 and any other reported solid acids to date, as determined by 1H and 31P solid-state NMR. These 2D solid acids show extraordinary catalytic performance in biomass conversion to fuels, superior to that of H3PW12O40, HCl and H2SO4. Theoretical calculations and control experiments reveal that H-bond based interactions between the polymer and montmorillonite facilitate the unusually high acid strengths found in these samples.

Effect of Fe/Fe2O3 loading on the catalytic activity of sulfonated single-walled carbon nanohorns for the esterification of palmitic acid

Poonjarernsilp, Chantamanee,Sano, Noriaki,Sawangpanich, Nut,Charinpanitkul, Tawatchai,Tamon, Hajime

, p. 4936 - 4943 (2014)

The effect of dispersion of Fe/Fe2O3 nanoparticles in sulfonated single-walled carbon nanohorns (SO3H/SWCNHs) on their catalytic activity for the esterification of palmitic acid was investigated. A gas-injected arc-in-water (GI-AIW) method was employed to initially synthesize SWCNHs dispersed with iron nanoparticles (Fe-SWCNHs). The Fe-loading amount in the Fe-SWCNHs was varied by changing the number of Fe wires inserted in an anode. The results showed that Fe-loading amount proportionally increased from 6 to 13 wt% with an increase in the number of Fe wires. The surfaces of the Fe-SWCNHs were functionalized with acid functional groups by two sequential steps: impregnation of sulphuric acid and calcination in air. From the characterization results, their acid site concentrations were estimated to be 5.6-8.5 mmol g-1, suggesting that the catalyst was a solid superacid catalyst. XRD analyses indicated that most of the Fe was transformed to α-Fe2O3. The catalytic activity of the SO3H/Fe-SWCNHs for the esterification of palmitic acid was evaluated to investigate the influence of the Fe-loading on their catalytic activity. The results showed that the yield of methyl palmitate was significantly enhanced by an increase in the Fe-loading amount. It was discovered that the catalytic activity and the magnetic susceptibility of SO3H/Fe-SWCNHs can be preserved during repeated use, if the Fe-loading amount is large enough.

IRISTECTORENES A AND C-G, MONOCYCLIC TRITERPENE ESTERS FROM IRIS TECTORUM

Seki, Katsura,Tomihari, Toshiya,Haga, Kazuo,Kaneko, Ryohei

, p. 425 - 432 (1994)

Six new triterpene esters, iristectorenes A and C-G, along with one known one have been found in the seeds of Iris tectorum.On the basis of spectroscopic methods and chemical evidence, the esters were established to be 3--2,3-dimethyl-6-(1-methyl-2-oxoethylidene)cyclohexyl>propyl> (Z)-9-tetradecanoate, (Z)-11-hexadecanoate, (Z,Z)-9,12-octadecadienoate, hexadecanoate, (Z)-11-octadecenoate and octadecanoate, respectively.

Anti-inflammatory metabolites from endophytic fungus Fusarium sp

Khayat, Maan T.,Ibrahim, Sabrin R.M.,Mohamed, Gamal A.,Abdallah, Hossam M.

, p. 104 - 109 (2019)

Three new ergosterol derivatives, namely, fusaristerols B [(22E,24R)-3-palmitoyl-19(10→6)-abeo-ergosta-5,7,9,22-tetraen-3β-ol] (1), C [(22E,24R)-ergosta-7,22-diene-3β,6β,9α-triol] (3), and D [(22E,24R)-ergosta-7,22-diene-3β,5α,6β,9α-tetraol 6-acetate] (4), along with (22E,24R)-5β,8β-epidioxyergosta-22-en-3β-yl decanoate (2) and (22E,24R)-ergosta-7,22-dien-3β-ol (5), were isolated and characterized from the endophytic fungus Fusarium sp. isolated from Mentha longifolia L. (Labiatae) roots growing in Saudi Arabia. The structures of the isolated metabolites were verified based on UV, IR, NMR (1D and 2D), HRMS, and a comparison with the literature. All the metabolites were assessed for 5-lipoxygenase (5-LOX) inhibitory potential. Compounds 1 and 2 possessed 5-LOX inhibitory potential with an IC50s of 3.61 and 2.45 μM, respectively, compared to that of indomethacin (IC50 1.17 μM). In addition, their structure-activity relationship was discussed.

GC-EI-MS analysis of fatty acid composition in brain and serum of twitcher mouse

Zanfini, Assunta,Dreassi, Elena,Berardi, Anna,Piomboni, Paola,Costantino-Ceccarini, Elvira,Luddi, Alice

, p. 1115 - 1125 (2014)

Globoid cell leukodystrophy or Krabbe disease is an inherited autosomal recessive disorder caused by mutations in the galactosylceramidase gene. The objective of the study was to present information about the fatty acid (FA) composition of the brain and serum of twitcher mice, a mouse model of Krabbe disease, compared to wild type, in order to identify biomarker of disease progression. We defined the FA profiles by identifying the main components present in serum and brain using GC-EI-MS analysis. The FA percentage composition was measured and data were analyzed considering the disease and the mouse age as experimental factors. Significant correlations were established, both in brain and in serum, in the fatty acid percentage composition of twitcher compared to wild type mice. The most abundant saturated fatty acid in brain was the palmitic acid (C16:0) with mean values significantly increased in twitcher mouse (p = 0.0142); moreover, three monounsaturated, three polyunsaturated (PUFA) and a plasmalogen were significantly correlated to disease. In the serum highly significant differences were observed between the two groups for three polyunsaturated fatty acids. In fact, the docosahexaenoic acid (C22:6n3c) content was significantly increased (p = 0.0116), while the C20 PUFA (C20:3n6c and C20:5n3c) were significantly decreased in twitcher serum samples. Our study shows a specific FA profile that may help to define a possible pattern that could distinguish between twitcher and wild type; these data are likely to provide insight in the identification of new biomarkers to monitor the disease progression and thereby permit the critical analysis of therapeutic approaches.

C-Arylcalix[4]pyrogallolarene sulfonic acid: A novel and efficient organocatalyst material for biodiesel production

Jumina,Setiawan, Hamid Rohma,Triono, Sugeng,Kurniawan, Yehezkiel Steven,Priastomo, Yoga,Siswanta, Dwi,Zulkarnain, Abdul Karim,Kumar, Naresh

, p. 252 - 259 (2020)

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Esters, retroesters, and a retroamide of palmitic acid: Pool for the first selective inhibitors of N-palmitoylethanolamine-selective acid amidase

Vandevoorde, Séverine,Tsuboi, Kazuhito,Ueda, Natsuo,Jonsson, Kent-Olov,Fowler, Christopher J.,Lambert, Didier M.

, p. 4373 - 4376 (2003)

Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of "N-palmitoylethanolamine hydrolase" described so far. These compounds are devoid of affinity for CB1 and CB 2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.

Fructose induces transketolase flux to promote pancreatic cancer growth

Liu, Haibo,Huang, Danshan,McArthur, David L.,Boros, Laszlo G.,Nissen, Nicholas,Heaney, Anthony P.

, p. 6368 - 6376 (2010)

Carbohydrate metabolism via glycolysis and the tricarboxylic acid cycle is pivotal for cancer growth, and increased refined carbohydrate consumption adversely affects cancer survival. Traditionally, glucose and fructose have been considered as interchangeable monosaccharide substrates that are similarly metabolized, and little attention has been given to sugars other than glucose. However, fructose intake has increased dramatically in recent decades and cellular uptake of glucose and fructose uses distinct transporters. Here, we report that fructose provides an alternative substrate to induce pancreatic cancer cell proliferation. Importantly, fructose and glucose metabolism are quite different; in comparison with glucose, fructose induces thiaminedependent transketolase flux and is preferentially metabolized via the nonoxidative pentose phosphate pathway to synthesize nucleic acids and increase uric acid production. These findings show that cancer cells can readily metabolize fructose to increase proliferation. They have major significance for cancer patients given dietary refined fructose consumption, and indicate that efforts to reduce refined fructose intake or inhibit fructose-mediated actions may disrupt cancer growth. 2010 AACR.

A heteropolyacid-based ionic liquid as a thermoregulated and environmentally friendly catalyst in esterification reaction under microwave assistance

Duan, Xixin,Sun, Guiru,Sun, Zhong,Li, Jianxin,Wang, Shengtian,Wang, Xiaohong,Li, Shiwu,Jiang, Zijiang

, p. 125 - 128 (2013)

A new kind of heteropolyacid (HPA) ionic liquid [(CH3) 3NCH2CH2OH]H2PW12O 40 (ChH2PW) has been synthesized using choline chloride and H3PW12O40 (HPW) as precursors. The catalyst exhibited a novel switchable property based on temperature. The separation of the catalyst would be explored by simply decreasing reaction temperature without appreciable loss. Excellent conversions (97%) for esterification have been obtained under microwave-accelerated conditions.

Antiproliferative and apoptotic effects of compounds from the flower of Mammea siamensis (Miq.) T. Anders. on human cancer cell lines

Tung, Nguyen Huu,Uto, Takuhiro,Sakamoto, Ayana,Hayashida, Yuka,Hidaka, Yuuki,Morinaga, Osamu,Lhieochaiphant, Sorasak,Shoyama, Yukihiro

, p. 158 - 162 (2013)

On the search for anti-cancer compounds from Thai traditional herb medicines, a bioassay-guided fractionation and chemical investigation of the methanol extract of Mammea siamensis flower resulted in the isolation and identification of eight compounds (1-8) including a novel geranylated coumarin, namely mammeanoyl (2), and seven known compounds (1 and 3-8). The structure of new compound 2 was elucidated based on the extensive spectroscopic and chemical methods. Among the isolated compounds, three structurally related coumarins 3, 4, and 5 showed significant antiproliferative activities against human leukemia and stomach cancer cell lines. However, these compounds did not affect the cell viabilities of colon cancer, hepatoma, and normal skin fibroblast cell lines. Further analysis demonstrated that the morphological features of apoptosis including DNA fragmentation and chromatin condensation were observed in human leukemia HL-60 cells treated with compounds 3, 4, and 5. In addition, compound 3 led to caspase-3 activation and cleavage of poly (ADP-ribose) polymerase (PARP), and compound 3-induced DNA fragmentation was inhibited by caspase-specific inhibitors. These results suggest that compound 3, 4, and 5 exert antiproliferative actions through apoptotic cell death in leukemia cells and these compounds may have the potential to be developed into new anti-cancer drug candidates.

Lipidyl pseudopteranes A-F: Isolation, biomimetic synthesis, and PTP1B inhibitory activity of a new class of pseudopteranoids from the Gorgonian Pseudopterogorgia acerosa

Kate, Abhijeet S.,Aubry, Isabelle,Tremblay, Michel L.,Kerr, Russell G.

, p. 1977 - 1982 (2008)

Novel lipidyl pseudopteranoids, lipidyl pseudopteranes A-F (1-6), have been isolated from the soft coral Pseudopterogorgia acerosa collected from the Bahamas. Structure elucidation of the six new compounds was based on 1D and 2D NMR data and mass spectrometry, and a biomimetic synthesis of 1 from pseudopterolide (7) was used to help establish its absolute configuration. These structures represent the first report of a pseudopterane diterpene with a fatty acid moiety. Lipidyl pseudopteranes A and D exhibited modest yet selective inhibitory activity against protein tyrosine phosphatase 1B, a promising drug target.

Water-tolerant heteropolyacid on magnetic nanoparticles as efficient catalysts for esterification of free fatty acid

Duan, Xixin,Liu, Yue,Zhao, Qian,Wang, Xiaohong,Li, Shiwu

, p. 13748 - 13755 (2013)

Heteropolyacids (HPAs) supported on magnetic nanoparticles (MNPs) have been prepared by a simple acid-base interaction between functionalized magnetic nanoparticles and HPAs. The surface of the catalyst had been modified by organic groups to protect the catalytic sites from destruction by water. The hybrid SiO2-MNP-HPW consists of a core of magnetic iron oxide MNPs, silica shell, amino-silica and organic groups on the surface, which catalyzed the esterification of palmitic acid with methanol to give 90.4% FFA conversion within 2 h and a high TOF of 4.95 × 102 h-1 under mild reaction conditions. The catalytic performance compared favourably to other solid acid catalysts, demonstrating the advantage of the small size of catalyst particles in reducing mass transfer limitations and providing the substrates with better access to the catalyst sites on the surface of carriers. The catalysts are easily separable from the reaction mixture under a magnetic field and showed high stability and recyclability, with no significant loss of productivity after five cycles of esterification.

Catalytic deoxygenation of oleic acid in continuous gas flow for the production of diesel-like hydrocarbons

Arend, Matthias,Nonnen, Thomas,Hoelderich, Wolfgang F.,Fischer, Jürgen,Groos, Jeremie

, p. 198 - 204 (2011)

Continuous gas phase deoxygenation of oleic acid in the presence of hydrogen employing a granular 2 wt% Pd/C catalyst was investigated under solvent free conditions. Conversion of oleic acid and selectivity to the desired diesel-like C17 hydrocarbons heptadecane and heptadecenes was studied at different reaction conditions such as temperature, gas flow and catalyst amount. The best hydrocarbon yield was achieved with low reaction temperatures, high catalyst amounts and high hydrogen flows. To further decrease the reaction temperature but yet maintain a pure gas phase reaction, reactions were conducted in vacuum. Furthermore, water was added in varying amounts to support desorption and to determine if catalyst deactivation could be overcome. The deoxygenation catalyst was characterized by nitrogen adsorption isotherms (BET; Brunauer-Emmet-Teller method), X-ray powder diffraction (XRD), thermogravimetric analysis (TGA) and field emission scanning electron microscopy (FESEM).

A new triterpenoid ester from lobelia sessilifolia

Sun, Jiaming,Wang, Xiuli,Zhang, Hui,Yang, Junshan

, p. 416 - 418 (2012)

One novel triterpenoid ester, oleanol 28-aldehyde 3-Oβ-palmitate (1), was isolated from the aerial part of Lobelia sessilifolia Lamb. along with seven known compounds, namely two triterpenoid esters (2, 3), one sterol (4), two coumarins (5, 6), and two triterpenes (7, 8). The structure of 1 was established on the basis of spectroscopic and chemical data.

Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

Beck, Paulo,Dos Santos, Juliane M.,Kuhn, Bruna L.,Moreira, Dayse N.,Flores, Alex F. C.,Martins, Marcos A. P.,D'Oca, Marcelo G. M.,Piovesan, Luciana A.

, p. 2122 - 2127 (2012)

A series of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters was synthesized by the cyclocondensation of respective fatty hydrazides with 4-alkoxy-1,1,1-trialomethyl-3-alquen-2-ones. Efficient and regiospecific cyclizations catalyzed by BF3·MeOH gave the desired products in good to excellent yields and at high purity.

Lipoteichoic acid anchor triggers Mincle to drive protective immunity against invasive group A Streptococcus infection

Imai, Takashi,Matsumura, Takayuki,Mayer-Lambertz, Sabine,Wells, Christine A.,Ishikawa, Eri,Butcher, Suzanne K.,Barnett, Timothy C.,Walker, Mark J.,Imamura, Akihiro,Ishida, Hideharu,Ikebe, Tadayoshi,Miyamoto, Tomofumi,Ato, Manabu,Ohga, Shouichi,Lepenies, Bernd,Van Sorge, Nina M.,Yamasaki, Sho

, p. E10662 - E10671 (2018)

Group A Streptococcus (GAS) is a Gram-positive bacterial pathogen that causes a range of diseases, including fatal invasive infections. However, the mechanisms by which the innate immune system recognizes GAS are not well understood. We herein report that the C-type lectin receptor macrophage inducible C-type lectin (Mincle) recognizes GAS and initiates antibacterial immunity. Gene expression analysis of myeloid cells upon GAS stimulation revealed the contribution of the caspase recruitment domain-containing protein 9 (CARD9) pathway to the antibacterial responses. Among receptors signaling through CARD9, Mincle induced the production of inflammatory cytokines, inducible nitric oxide synthase, and reactive oxygen species upon recognition of the anchor of lipoteichoic acid, monoglucosyldiacylglycerol (MGDG), produced by GAS. Upon GAS infection, Mincle-deficient mice exhibited impaired production of proinflammatory cytokines, severe bacteremia, and rapid lethality. GAS also possesses another Mincle ligand, diglucosyldiacylglycerol; however, this glycolipid interfered with MGDG-induced activation. These results indicate that Mincle plays a central role in protective immunity against acute GAS infection.

A new ceramide from a new species of spongia sponge

Guan, Zhi,Zeng, Longmei

, p. 287 - 288 (2010)

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Sterols and Fatty Acids of the Harmful Dinoflagellate Cochlodinium polykrikoides

Giner, José-Luis,Ceballos, Harriette,Tang, Ying-Zhong,Gobler, Christopher J.

, p. 249 - 252 (2016)

Sterol and fatty acid compositions were determined for Cochlodinium polykrikoides, a toxic, bloom-forming dinoflagellate of global significance. The major sterols were dinosterol (40% of total sterols), dihydrodinosterol (32%), and the rare 4α-methyl Δ8(14) sterol, amphisterol (23%). A minor sterol, 4α-methylergost-24(28)-enol was also detected (5.0%). The fatty acids had a high proportion of PUFAs (47%), consisting mainly of EPA (20%) and the relatively uncommon octadecapentaenoic acid (18: 5, 22%). While unlikely to be responsible for toxicity to fish, these lipids may contribute to the deleterious effects of this alga to invertebrates.

Erratum: Efficient conversion of triacylglycerols and fatty acids to biodiesel in a microwave reactor using metal triflate catalysts (Organic and Biomolecular Chemistry (2010) 8 (4753-4756) DOI: 10.1039/c0ob00014k)

Socha, Aaron M.,Sello, Jason K.

, p. 5701 - 5701 (2010)

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Identification and α -Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus

Bao, Li,Chen, Baosong,Han, Junjie,Liu, Hongwei,Ma, Ke,Wang, Wenzhao

, p. 571 - 578 (2020)

Hericium erinaceus is a very popular edible and medicinal mushroom used for the treatment of enervation and gastrointestinal diseases in Eastern Asia. Chemical investigation on the fruiting body of Hericium erinaceus led to the isolation of 4 new (1 - 4) and 10 known meroterpenoids (5 - 14). The structures of new compounds were determined via analysis of NMR and MS data in combination with chemical derivatization. The inhibitory activities of 1 - 14 against α -glucosidase were evaluated using p -nitrophenyl- α -D-glucopyranoside, sucrose, or maltose as substrate. Compounds 6, 9, 11 - 13 were demonstrated to show the α -glucosidase inhibitory activities. This work confirms the potential of H. erinaceus in the treatment of diabetes.

Production of biodiesel through esterification of palmitic acid using 12-tungestoposphoric acid supported on nanocavity of aluminium incorporated mesoporous SBA-15

Fazaeli, Razieh,Aliyan, Hamid

, p. 676 - 681 (2015)

The main aim of this research is to develop efficient and environmentally benign heterogeneous catalysts for biodiesel production. For this purpose, H3PW12O40 (PW12) supported on Al-functionalized SBA-15 mesoporous molecular sieve featuring a well-defined three-dimensional (3D) mesoporosity were studied, and the prepared catalyst (PW12/Al-SBA-15) was tested for the esterification process of palmitic acid to produce methyl palmitate as a kind of biodiesel. The effects of the methanol/oil ratio, catalyst amounts, reaction time, and reaction temperature on the conversion are also reported in this paper. More importantly, by using a 35 wt % of PW12/Al-SBA-15 with methanol/oil molar ratio of 20: 1 at reflux of methanol, the oil conversion of 98% after 8 h of reaction, could be achieved over the solid catalyst for at least 6 cycles under mild conditions.

Non-cannabinoid constituents from a high potency Cannabis sativa variety

Radwan, Mohamed M.,ElSohly, Mahmoud A.,Slade, Desmond,Ahmed, Safwat A.,Wilson, Lisa,El-Alfy, Abir T.,Khan, Ikhlas A.,Ross, Samir A.

, p. 2627 - 2633 (2008)

Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L. variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and β-sitosteryl-3-O-β-d-glucopyranoside-2′-O-palmitate (6). In addition, five known compounds, α-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and β-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and anti-oxidant activities. Compounds 2-4 were inactive as analgesics.

Dual-catalytic decarbonylation of fatty acid methyl esters to form olefins

Fieser, Megan E.,Schimler, Sydonie D.,Mitchell, Lauren A.,Wilborn, Emily G.,John, Alex,Hogan, Levi T.,Benson, Brooke,LaPointe, Anne M.,Tolman, William B.

, p. 7669 - 7672 (2018)

The homogeneous dehydrative decarbonylation of fatty acid methyl esters (FAMEs) to form olefins is reported. In order to facilitate cleavage of the unactivated acyl C-O bond of the alkyl ester, a one pot dual-catalytic directing group strategy was developed through optimization of the individual transesterification and decarbonylation reaction steps.

Sustainable production of biodiesel and transformation of glycerol to glycerol laurate esters over inner diameter-controlled sulfonic acid functionalized ethyl-bridged-organosilica nanotubes

Guo, Yihang,Liu, Jingyu,Song, Daiyu,Wu, Qingyin,Zhang, Chaoyue,Zhang, Qingqing

, (2021)

Solid acid-catalyzed biodiesel production from inedible oils offers a promising mean to reduce the cost of feedstocks and avoid the competition with edible oil market. Here we demonstrate a series of inner diameter-controlled sulfonic acid functionalized ethyl-bridged-organosilica nanotubes (Ar/PrSO3H–Si(Et)Si) by a toluene swollen mixed Pluronic surfactant micelle-templating co-condensation route for transesterification of tripalmitin or plant oils with methanol to produce fatty acid methyl esters and esterification of glycerol with lauric acid to produce mono- and di-glycerol esters. By combination of superstrong Br?nsted acidity, unique hollow tubular nanostructure, excellent porosity properties and hydrophobic surface, the Ar/PrSO3H–Si(Et)Si nanotubes display higher catalytic activity as compared with acidic resin and zeolite. Additionally, the inner diameters and lengths of Ar/PrSO3H–Si(Et)Si nanotubes influence the activity obviously. The Ar/PrSO3H–Si(Et)Si nanotubes also show excellent catalytic reusability, attributing to covalent bonding of Ar/PrSO3H groups within silica/carbon framework and surface hydrophobicity of the catalysts.

Cucumol B, a new triterpene benzoate from Cucumis melo seeds with cytotoxic effect toward ovarian and human breast adenocarcinoma

Ibrahim, Sabrin Ragab Mohamed,Khedr, Amgad Ibrahim Mansour,Mohamed, Gamal Abdallah,Zayed, Mohamed Fathalla,El-Kholy, Amal Abd-Elmoneim Soliman,Al Haidari, Rwaida Adel

, p. 1112 - 1118 (2019)

Phytochemical investigation of the methanolic extract of Cucumis melo L. (Cucurbitaceae) seeds furnished a new triterpene benzoate derivative: cucumol B (1) and four known flavonoids: quercetin-3-O-β-D-glucopyranosyl-(1→6)-α-L-rhamnopyranoside (2), quercetin-3-O-β-D-glucopyranoside (3), quercetin (4), and luteolin (5). Their structures were identified by UV, IR, 1D (13C and 1H), 2D (HSQC, 1H-1H COSY, HMBC, and NOESY) NMR, and HRESIMS spectral as well as comparing with literature data. Compound 1 has been assessed for the in vitro cytotoxic effect against SKOV-3, MCF-7, and HCT-116 cell lines. It had selective and potent effect toward SKOV-3 and MCF-7 cell lines with IC50s 2.05 and 0.41 μM, respectively, in comparison to doxorubicin (IC50s 0.32 and 0.05 μM). However, it showed moderate activity toward HCT-116 cell line with IC50 8.27 μM.

Organosulfonic acid-functionalized mesoporous silicas for the esterification of fatty acid

Mbaraka, Isa K.,Radu, Daniela R.,Lin, Victor S.-Y.,Shanks, Brent H.

, p. 329 - 336 (2003)

The transesterification of vegetable oils with short-chain alcohols has shown potential application as an intermediate for value-added products, e.g., fatty alcohols and biodiesel. Organosulfonic acid-functionalized mesoporous silicas were synthesized in a one-step approach of co-condensing inorganic-organic reagents in the presence of different surfactant templates with in situ oxidation of the thiol groups to the sulfonic acid groups. The resulting materials were tested for their catalytic performance in the esterification of fatty acid with methanol to produce methyl esters. The performance of the functionalized mesoporous materials demonstrated a strong dependence on the median pore diameter of the catalyst as well as the acidic strength of the organosulfonic acid group. A comparison of the activity of the organosulfonic acid-functionalized silicas in the esterification to that of standard acidic resins showed the potential of rational catalysis design using organic-inorganic mesoporous materials.

PALMILYCORINE AND LYCORISIDE: ACYLOXY AND ACYLGLUCOSYLOXY ALKALOIDS FROM CRINUM ASIATICUM

Ghosal, Shinbath,Shanthy, Amirthalingam,Kumar, Anand,Kumar, Yatendra

, p. 2703 - 2706 (1985)

Two new types of alkaloidal conjugates, a C16-acyloxy derivative, named palmilycorine, and an acylglucosyloxy derivative, named lycoriside, were isolated from the fruits of Crinum asiaticum.The presence of these compounds was also detected in the fleshy scale leaves and in roots of these species.The structures of the two compounds were established as 1-O-palmitoyllicorine (1) and lycorine-1-O-(6'-O-palmitoyl-β-D-glucopyranoside) (2), respectively, on the basis of chemical transformation and comprehensive spectral evidence.The biological effects of the alkaloids were evaluated. Key Word Index - Crinum asiaticum; Amaryllidaceae; fruits; alkaloids; alkaloidal conjugates; palmilycorine, 1-O-palmitoyllicorine; lycoriside, lycorine-1-O-(6'-O-palmitoyl-β-D-glucopyranoside); lycorine-1-O-β-D-glucoside; promoters of cell viability, cell growth and root growth.

Glycerogalactolipids from the fruit of Lycium barbarum

Gao, Zengping,Ali, Zulfiqar,Khan, Ikhlas A.

, p. 2856 - 2861 (2008)

Four glycerogalactolipids (1-4), together with 11 other previously known homologues were isolated from the fruit of Lycium barbarum. Their structures were elucidated by chemical analyses including regio-selective enzymatic, alkaline and acidic hydrolyses and spectroscopic methods involving GCMS, HRESIMS and 1D and 2D NMR, respectively.

Chemoenzymatic Generation of Phospholipid Membranes Mediated by Type i Fatty Acid Synthase

Khanal, Satyam,Brea, Roberto J.,Burkart, Michael D.,Devaraj, Neal K.

, p. 8533 - 8537 (2021)

The de novo formation of lipid membranes from minimal reactive precursors is a major goal in synthetic cell research. In nature, the synthesis of membrane phospholipids is orchestrated by numerous enzymes, including fatty acid synthases and membrane-bound acyltransferases. However, these enzymatic pathways are difficult to fully reproduce in vitro. As such, the reconstitution of phospholipid membrane synthesis from simple metabolic building blocks remains a challenge. Here, we describe a chemoenzymatic strategy for lipid membrane generation that utilizes a soluble bacterial fatty acid synthase (cgFAS I) to synthesize palmitoyl-CoA in situ from acetyl-CoA and malonyl-CoA. The fatty acid derivative spontaneously reacts with a cysteine-modified lysophospholipid by native chemical ligation (NCL), affording a noncanonical amidophospholipid that self-Assembles into micron-sized membrane-bound vesicles. To our knowledge, this is the first example of reconstituting phospholipid membrane formation directly from acetyl-CoA and malonyl-CoA precursors. Our results demonstrate that combining the specificity and efficiency of a type I fatty acid synthase with a highly selective bioconjugation reaction provides a biomimetic route for the de novo formation of membrane-bound vesicles.

Design and synthesis of micro-meso-macroporous polymers with versatile active sites and excellent activities in the production of biofuels and fine chemicals

Liu, Fujian,Liu, Chen,Kong, Weiping,Qi, Chenze,Zheng, Anmin,Dai, Sheng

, p. 6536 - 6544 (2016)

Micro-meso-macroporous polymers (MOPs) grafted with versatile functional groups, such as sulfonate, amine, triazole, pyridine, strong acidic ionic liquids and triphenylphosphine, were synthesized by in situ cross-linking of different functional molecules with 1,4-bis(chloromethyl)benzene in the presence of Lewis acid catalysts without using additional templates. The resultant hyper-cross-linked nanoporous polymers show unique characteristics such as large BET surface areas (up to 1523 m2 g-1), abundant micro-meso-macropores (4.5-131 nm), and tunable and versatile active sites (acid, base and palladium). These functional polymers exhibit excellent activities and good reusability in biomass conversions, cross-coupling reactions and condensation. The catalytic activities are much better than those of various conventional catalysts such as H3PW12O40, SBA-15-SO3H, Amberlyst 15, and mesoporous H-ZSM-5 Pd/C and even as comparable as those of homogeneous H2SO4 and HCl in the depolymerization of crystalline cellulose into fine chemicals and towards transesterification to biodiesel. This work highlights a low cost route to the synthesis of solid catalysts based on functional nanoporous polymers for catalyzing the production of clean biofuels and fine chemicals.

High-temperature synthesis of strong acidic ionic liquids functionalized, ordered and stable mesoporous polymers with excellent catalytic activities

Liu, Fujian,Zuo, Shufeng,Kong, Weiping,Qi, Chenze

, p. 1342 - 1349 (2012)

Strong acidic ionic liquids functionalized, ordered and stable mesoporous phenol-formaldehyde resins (OMR-ILs) monoliths have been successfully synthesized from the treatment of ordered mesoporous resins (OMR-[HMTA]) using 1,3-propanesultone, followed by ion exchanged using various strong acids. The OMR-[HMTA] samples could be synthesized by the assembly of block copolymer template of F127 with preformed resol, which could be obtained from heating a mixture of phenol and formaldehyde at 70 °C; during curing processes, certain contents of the hexamethyltetramine (HMTA) cross linker were also introduced, after hydrothermal treatment at 200 °C for 20 h, calcination at 360 °C under nitrogen, OMR-[HMTA] samples with opened mesopores were obtained. Characterizations suggest that OMR-ILs have ordered and stable mesospores, high BET surface areas, and strong acid strength. Interestingly, OMR-ILs show much higher catalytic activities and recyclability in the esterification of acetic acid with cyclohexanol, hydration of propylene oxide, Peckmann reaction of resorcinol with ethyl acetoacetate and transesterification of tripalmitin with methanol than those of Amberlyst 15, sulfonic group functional ordered mesoporous silicas and acidic zeolites, which were even comparable with that of H2SO4. The unique features of OMR-ILs such as superior thermal stability, excellent catalytic activities and recyclability, will be potentially important for their applications in industry.

Four new phorbol diesters from Croton tiglium and their cytotoxic activities

Zhang, Xiao-Long,Khan, Ashfaq-Ahmad,Wang, Lun,Yu, Kai,Li, Fu,Wang, Ming-Kui

, p. 82 - 86 (2016)

Phytochemical investigation of the seeds of Croton tiglium resulted in the isolation and structure elucidation of four new 4-deoxy-4β-phorbol diesters (1-4) named as 12-O-tiglylphorbol-4-deoxy-4β-phorbol-13-acetate (1), 12-O-tiglylphorbol-4-deoxy-4β-phorbol-13-hexadecanoate (2), 13-O-acetylphorbol-4-deoxy-4β-phorbol-20-oleate (3) and 13-O-acetylphorbol-4-deoxy-4β-phorbol-20-linoleate (4), respectively. The structures of the new compounds were established by 1D, 2D-NMR and HR-ESI-MS spectroscopic data and chemical degradation experiments. The cytotoxic activities of compounds 1-4 were evaluated against hepatic tumor cell lines (SNU387 and SNU398). Among these compounds, compound 4 exhibited the most potent activity against the SNU387 with IC50 value of 0.71 μM.

Determining the role of oxygen vacancies in palmitone selectivity and coke formation over acid metal oxide catalysts for the ketonization of methyl palmitate

Guntida, Adisak,Jongsomjit, Bunjerd,Praserthdam, Piyasan,Praserthdam, Supareak,Rattanachartnarong, Thanwarat,Sooknoi, Tawan,Weerachawanasak, Patcharaporn

, (2021/11/11)

In the present study, TiO2, CeO2, MnO2, and ZrO2 catalysts were used to investigate the catalytic performance in methyl palmitate ketonization. The reaction was accelerated by weak Lewis acid, while the oxygen v

Chemically Modified Lipase from Thermomyces lanuginosus with Enhanced Esterification and Transesterification Activities

Noro, Jennifer,Cavaco-Paulo, Artur,Silva, Carla

, p. 4524 - 4531 (2021/09/02)

Lipase from Thermomyces lanuginosus is one of the most explored enzymes for the esterification of several added-value industrial compounds, such as biodiesel, fragrances, and flavors. Its selectivity in these reactions is mostly related with its activity towards small alcohols. In this work, the impact of the chemical modification, with 4 dodecyl chains at its surface, was evaluated regarding its transesterification and esterification activities, comparing with the native form. Linear size-differentiated alcohols (from 1 to 20 carbons in the aliphatic chain) were used to explore for the first time the effect of the chain length in both transesterification and esterification reactions, using p-nitrophenyl palmitate and oleic acid as model compounds, respectively. The chemically modified lipase showed an outstanding improvement of its catalytic performance than the native enzyme, being this increase directly proportional to the size of the alcohols chain used as substrates. The enormous potential and remarkable versatility of this novel super catalyst was here demonstrated, where diverse types of esters, differing in their potential applications (biodiesel, cosmetics, fine chemistry), were efficiently synthesized. The produced esters were fully characterized by 1H NMR, GC-MS, and FTIR.

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

Wang, Jingjing,Jiang, Feng,Tao, Chaofu,Yu, Han,Ruhlmann, Laurent,Wei, Yongge

supporting information, p. 2652 - 2657 (2021/04/21)

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

Synthesis and characterization of biodegradable palm palmitic acid based bioplastic

Japir, Abd Al-Wali,Salih, Nadia,Salimon, Jumat

, p. 585 - 599 (2021/07/26)

This study involves the quantitative analysis of high free fatty acid crude palm oil, the separation of palmitic acid and synthesis of palm palmitic acid-based bioplastic. Synthesis of dimethyl 2-tetradecylmalonate (DMTDM) using methyl palmitate (MP) with sodium hydride (NaH) in the presence of reactive solvent of dimethyl carbonate (DMC) was carried out. The reaction conditions comprise at a mole ratio of MP: DMC: NaH: Dimethylformamide (DMF) (0.1:2:0.25:1) at 60 °C for 14 h with 88.3 ± 1.4% yield. FTIR spectra of DMTDM showed the ester carbonyl group at 1740 cm-1. The polymerization of DMTDM with 1,6-hexandiol or 1,12-dodecandiol was carried out using titanium (IV) isopropoxide Ti(OiPr)4 as the catalyst and reaction time of 24 h. The results showed that the poly(dodecyl 2-tetradecylmalonte) (PDTDM) exhibited good thermal properties compared to poly(hexyl 2-tetradecylmalonte) (PHTDM). The increase of the chain length of diol in PDTDM improved the thermal properties of polyester with glass transition, Tg of 13 °C and melting point of 51 °C with a molecular weight of 12508 Da and polydispersity index (PDI) of 1.4. In general, the synthetic polyesters can be used as internalplasticizer in bio-based industry.

Process route upstream and downstream products

Process route

methanol
67-56-1

methanol

4-nitrophenyl palmitate
1492-30-4

4-nitrophenyl palmitate

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

Conditions
Conditions Yield
With Thermomyces lanuginosus lipase; for 7h; Enzymatic reaction;
sitoindoside I
18749-71-8

sitoindoside I

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

Conditions
Conditions Yield
With sodium methylate; In methanol; for 3h; Title compound not separated from byproducts; Ambient temperature;
methanol
67-56-1

methanol

methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
108698-02-8

methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

methyl linoleate
16326-32-2

methyl linoleate

methyl arachidonate
2566-89-4

methyl arachidonate

(Z)-9-hexadecenoic acid methyl ester
1120-25-8,3913-63-1

(Z)-9-hexadecenoic acid methyl ester

Methyl oleate
112-62-9

Methyl oleate

Methyl linoleate
112-63-0

Methyl linoleate

(11Z)-11-icosenoic acid methyl ester
2390-09-2,3946-08-5

(11Z)-11-icosenoic acid methyl ester

methyl linolenate
301-00-8

methyl linolenate

methyl n-dodecanoate
111-82-0

methyl n-dodecanoate

methyl myristoate
124-10-7

methyl myristoate

pentadecanoic acid methyl ester
7132-64-1

pentadecanoic acid methyl ester

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

methyl margarate
1731-92-6

methyl margarate

Methyl stearate
112-61-8

Methyl stearate

methyl arachidate
1120-28-1

methyl arachidate

behenic acid methyl ester
929-77-1

behenic acid methyl ester

all-cis-8,11,14-eicosatrienoic acid methyl ester
21061-10-9

all-cis-8,11,14-eicosatrienoic acid methyl ester

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester
2734-47-6

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester
13487-42-8

cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester

myristoleic acid methyl ester
56219-06-8

myristoleic acid methyl ester

cis,trans-9,11-methyloctadecadienoate
35042-75-2

cis,trans-9,11-methyloctadecadienoate

Conditions
Conditions Yield
With potassium hydroxide; water; In methanol; at 55 ℃; for 1.5h;
methanol; With sulfuric acid; In water; at 20 - 55 ℃; for 1.5h; Product distribution / selectivity;
methanol; boron trifluoride; at 55 ℃; for 1.5h;
With water; sodium hydrogencarbonate; In hexane; Product distribution / selectivity;
methanol
67-56-1

methanol

methyl trans-2-octadecenoate
14663-11-7

methyl trans-2-octadecenoate

5,8,11-Eicosatrienoic acid, methyl ester

5,8,11-Eicosatrienoic acid, methyl ester

heneicosapentaenoic acid methyl ester

heneicosapentaenoic acid methyl ester

eicosadienoic acid methyl ester
88400-02-6

eicosadienoic acid methyl ester

docosapentaenoic acid methyl ester

docosapentaenoic acid methyl ester

docosatetraenoic acid methyl ester

docosatetraenoic acid methyl ester

docosadienoic acid methyl ester

docosadienoic acid methyl ester

palmitelaidic acid methyl ester
10030-74-7,3913-63-1

palmitelaidic acid methyl ester

Methyl oleate
112-62-9

Methyl oleate

Methyl linoleate
112-63-0

Methyl linoleate

methyl cis-13-docosenoate
1120-34-9

methyl cis-13-docosenoate

methyl cis-tetracos-15-enate
2733-88-2

methyl cis-tetracos-15-enate

methyl myristoate
124-10-7

methyl myristoate

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

methyl margarate
1731-92-6

methyl margarate

Methyl stearate
112-61-8

Methyl stearate

methyl arachidate
1120-28-1

methyl arachidate

behenic acid methyl ester
929-77-1

behenic acid methyl ester

methyl tetracosanoate
2442-49-1

methyl tetracosanoate

methyl (2E)-eicosenoate
10305-59-6

methyl (2E)-eicosenoate

methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate
37929-05-8

methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate

Conditions
Conditions Yield
With potassium hydroxide; at 48 - 52 ℃; for 4h;
methanol
67-56-1

methanol

canola oil

canola oil

methyl trans-2-octadecenoate
14663-11-7

methyl trans-2-octadecenoate

5,8,11-Eicosatrienoic acid, methyl ester

5,8,11-Eicosatrienoic acid, methyl ester

heneicosapentaenoic acid methyl ester

heneicosapentaenoic acid methyl ester

eicosadienoic acid methyl ester
88400-02-6

eicosadienoic acid methyl ester

docosapentaenoic acid methyl ester

docosapentaenoic acid methyl ester

docosatetraenoic acid methyl ester

docosatetraenoic acid methyl ester

docosadienoic acid methyl ester

docosadienoic acid methyl ester

palmitelaidic acid methyl ester
10030-74-7,3913-63-1

palmitelaidic acid methyl ester

Methyl oleate
112-62-9

Methyl oleate

Methyl linoleate
112-63-0

Methyl linoleate

methyl cis-13-docosenoate
1120-34-9

methyl cis-13-docosenoate

methyl cis-tetracos-15-enate
2733-88-2

methyl cis-tetracos-15-enate

methyl myristoate
124-10-7

methyl myristoate

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

methyl margarate
1731-92-6

methyl margarate

Methyl stearate
112-61-8

Methyl stearate

methyl arachidate
1120-28-1

methyl arachidate

behenic acid methyl ester
929-77-1

behenic acid methyl ester

methyl tetracosanoate
2442-49-1

methyl tetracosanoate

methyl (2E)-eicosenoate
10305-59-6

methyl (2E)-eicosenoate

methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate
37929-05-8

methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate

Conditions
Conditions Yield
With potassium hydroxide; at 48 - 52 ℃; for 4h;
methanol
67-56-1

methanol

mustard oil

mustard oil

methyl trans-2-octadecenoate
14663-11-7

methyl trans-2-octadecenoate

5,8,11-Eicosatrienoic acid, methyl ester

5,8,11-Eicosatrienoic acid, methyl ester

heneicosapentaenoic acid methyl ester

heneicosapentaenoic acid methyl ester

eicosadienoic acid methyl ester
88400-02-6

eicosadienoic acid methyl ester

docosapentaenoic acid methyl ester

docosapentaenoic acid methyl ester

docosatetraenoic acid methyl ester

docosatetraenoic acid methyl ester

docosadienoic acid methyl ester

docosadienoic acid methyl ester

palmitelaidic acid methyl ester
10030-74-7,3913-63-1

palmitelaidic acid methyl ester

Methyl oleate
112-62-9

Methyl oleate

Methyl linoleate
112-63-0

Methyl linoleate

methyl cis-13-docosenoate
1120-34-9

methyl cis-13-docosenoate

methyl cis-tetracos-15-enate
2733-88-2

methyl cis-tetracos-15-enate

methyl myristoate
124-10-7

methyl myristoate

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

methyl margarate
1731-92-6

methyl margarate

Methyl stearate
112-61-8

Methyl stearate

methyl arachidate
1120-28-1

methyl arachidate

behenic acid methyl ester
929-77-1

behenic acid methyl ester

methyl tetracosanoate
2442-49-1

methyl tetracosanoate

methyl (2E)-eicosenoate
10305-59-6

methyl (2E)-eicosenoate

methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate
37929-05-8

methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate

Conditions
Conditions Yield
With potassium hydroxide; at 48 - 52 ℃; for 4.5h;
methanol
67-56-1

methanol

((2S)-1-O-hexadecanoyl-2-O-docosanoyl)-3-O-[6-deoxy-6-amino-α-D-glucopyranoside]glycerol

((2S)-1-O-hexadecanoyl-2-O-docosanoyl)-3-O-[6-deoxy-6-amino-α-D-glucopyranoside]glycerol

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

behenic acid methyl ester
929-77-1

behenic acid methyl ester

Conditions
Conditions Yield
With sodium methylate; at 20 ℃; for 3h;
methanol
67-56-1

methanol

sodium methylate
124-41-4

sodium methylate

methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
108698-02-8

methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

methyl linoleate
16326-32-2

methyl linoleate

methyl arachidonate
2566-89-4

methyl arachidonate

(Z)-9-hexadecenoic acid methyl ester
1120-25-8,3913-63-1

(Z)-9-hexadecenoic acid methyl ester

Methyl oleate
112-62-9

Methyl oleate

Methyl linoleate
112-63-0

Methyl linoleate

(11Z)-11-icosenoic acid methyl ester
2390-09-2,3946-08-5

(11Z)-11-icosenoic acid methyl ester

methyl linolenate
301-00-8

methyl linolenate

methyl n-dodecanoate
111-82-0

methyl n-dodecanoate

methyl myristoate
124-10-7

methyl myristoate

pentadecanoic acid methyl ester
7132-64-1

pentadecanoic acid methyl ester

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

methyl margarate
1731-92-6

methyl margarate

Methyl stearate
112-61-8

Methyl stearate

methyl arachidate
1120-28-1

methyl arachidate

behenic acid methyl ester
929-77-1

behenic acid methyl ester

all-cis-8,11,14-eicosatrienoic acid methyl ester
21061-10-9

all-cis-8,11,14-eicosatrienoic acid methyl ester

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester
2734-47-6

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester
13487-42-8

cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester

myristoleic acid methyl ester
56219-06-8

myristoleic acid methyl ester

cis,trans-9,11-methyloctadecadienoate
35042-75-2

cis,trans-9,11-methyloctadecadienoate

Conditions
Conditions Yield
at 55 ℃; for 1.5h; Product distribution / selectivity;
sodium methylate
124-41-4

sodium methylate

sitoindoside I
18749-71-8

sitoindoside I

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

Conditions
Conditions Yield
In methanol; for 3h; Title compound not separated from byproducts; Ambient temperature;
methyl α-eleostearate
4175-47-7

methyl α-eleostearate

nonane
111-84-2

nonane

decane
124-18-5

decane

n-Undecane
1120-21-4

n-Undecane

dodecane
112-40-3

dodecane

Tridecane
629-50-5

Tridecane

tetradecane
629-59-4

tetradecane

Hexadecane
544-76-3

Hexadecane

methyl tridecanoate
1731-88-0

methyl tridecanoate

methyl myristoate
124-10-7

methyl myristoate

pentadecanoic acid methyl ester
7132-64-1

pentadecanoic acid methyl ester

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

methyl margarate
1731-92-6

methyl margarate

Methyl stearate
112-61-8

Methyl stearate

dimethyl heptadecane-1,17-dioate
19102-92-2

dimethyl heptadecane-1,17-dioate

dimethyl 1,18-octadecanedioate
1472-93-1

dimethyl 1,18-octadecanedioate

dimethyl 1,19-nonadecandioate
23130-41-8

dimethyl 1,19-nonadecandioate

1,18-octadecanoic acid dimethyl ester
42235-38-1

1,18-octadecanoic acid dimethyl ester

Methyl-2,6,10,14-tetramethylhexadecanoat

Methyl-2,6,10,14-tetramethylhexadecanoat

Conditions
Conditions Yield
methyl α-eleostearate; With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 100 ℃; for 2h; Schlenk technique; Inert atmosphere;
With palladium on activated charcoal; hydrogen; In ethanol; toluene; at 20 ℃; Schlenk technique;

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