- ON THE STRUCTURE OF MICELLES.
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Kinetic studies of micellar olefin oxidation by permanganate ion show that a terminal olefin is oxidized 2 orders of magnitude faster than internal olefins. This is interpreted in terms of coiling and disorder which place chain termini in the water-rich Stern region. The results are not consistent with the Dill-Flory and Fromherz models.
- Menger,Doll
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Read Online
- The action of hypochlorous acid on phosphatidylcholine liposomes in dependence on the content of double bonds. Stoichimetry and NMR analysis
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Kinetics of the consumption of hypochlorous acid in its reaction with double bonds of unsaturated phospholipids and fatty acids were measured using luminol chemiluminescence.Stoichiometry ratios between the consumption of HOCl/OCl- and the loss of double bonds vary from 2:1 to 1:1.Highest values were found in DMPC liposomes containing 5 molpercent oleic acid or OPPC.With increasing content of double bonds or higher numbers of double bonds in a fatty acid acyl chain ddue to incorporated unsaturated fatty acids or phospholipids in DMPC liposomes the stoichiometry ratio falls continuously to 1:1.A ratio of about 1:1 was observed in multilamellar and unilamellar liposomes composed of egg yolk phosphatidylcholine.Products of the reaction of oleic acid with hypochlorous acid were analysed by 1H-NMR spectroscopy.Chlorohydrins were formed in both DMPC liposomes containing 5 or 40 molpercent oleic acid.Keywords: Hypochlorous acid; Chlorohydrins; Double bond; Phospholipids; Fatty acids
- Arnhold, J.,Panasenko, O. M.,Schiller, J.,Vladimirov, Yu. A.,Arnold, K.
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Read Online
- THE ELCTRICAL CONDUCTANCE OF MOLTEN LEAD(II) 9,10-DIHYDROXYOCTADECANOATE AND SOME BINARY MIXTURES WITH LEAD(II) OCTADECANOATE
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Data are presented for electrical conductances of molten lead(II) 9,10-dihydroxyoctadecanoate and the system lead(II) octadecanoate-lead(II) 9,10-dihydroxyoctadecnoate.The lead(II) 9,10-dihydroxyoctadecanoate is prepared from 9,10-dihydroxyoctadecanoic acid which in turn is obtained from the oxidation of cis-9-octadecanoic acid by hydrogen peroxide in methanoic acid.For the mole fraction of lead(II) 9,10-dihydroxyoctadecanopate /= 0.03.The maximum is interpreted in terms of the current carriers (Pb(2+) ions) recting with the dihydroxy groups to form a bridged cyclo-acid.The observed low conductance of pure lead(II) 9,10-dohyroxyoctadecanoate and the decrease in conductance of the mixtures compared with lead(II) octadecanoate is suggested to be due to the relatively small dissociation of the dihydroxy soap.Activation energies for conductance in the low-temperature region show a steady decrease with increasing mole fraction of lead(II) 9,10-dihydroxyoctadecanoate up to a certain composition and then increase.Theis behaviour is attributed to a change in the microscopic structure of the melt owing to the increasingly dominant role of the substitued hydroxy groups.The activation energy for the pure dihydroxy soap is close to those of other lead(II) soap, suggesting that the major charge is probably the same, i.e. the Pb(2+) ion.
- Akanni, M. Sola,Mbaneme, P. Chuckwulozie
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Read Online
- STEREOCHEMISTRY OF β-HYDROXYDODECANOYL THIOESTER DEHYDRATION CATALYZED BY FATTY ACID SYNTHETASE FROM BREVIBACTERIUM AMMONIAGENES
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The pro-4S hydrogen of trans-α,β-dodecenoyl thioester was abstracted and a proton was added to the 2-Si face during the prototropic isomerization catalyzed by β-hydroxydodecenoyl thioester dehydrase.
- Saito, Kazuki,Kawaguchi, Akihiko,Seyama, Yousuke,Yamakawa, Tamio,Okuda, Shigenobu
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Read Online
- Design, synthesis and gelation of low molecular weight organo-gelators derived from oleic acid via, amidation
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In recent decades, gels have been widely considered for various medicinal purposes and, in particular, wound healing applications. In this regard, amides of oleic acids and 9, 10-dihydroxyoctadecanoic acid are synthesized and characterized with the help of modern analytical tools. Among the mentioned amide frameworks, N-(2-aminoethyl)-oleamide exhibits high order of gelation not only with different organic solvents such as n-hexane and DMSO but also with different edible oils such as sesame oil, mustard oil, coconut oil and citriodora oil. Here, we briefly discuss the optimization of gelation conditions for the synthesized amides as organo-gelator, in addition to that the minimum gelation concentration and gelation temperature have also been studied.
- Gupta, Gaurav R.,Joshi, Narendra S.,Phalak, Raju P.,Waghulde, Govinda P.
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p. 1109 - 1116
(2021/11/17)
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- PROCESS FOR THE PREPARATION OF HYDROPEROXY ALCOHOLS USING A HETEROGENOUS CATALYST
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The present invention relates to a process for preparing hydroperoxy alcohols using hydrogen peroxide as an oxidant in a solvent selected from water-soluble carboxylic acids, in the presence of a metallic mixed oxide heterogeneous catalyst. It also pertains to the use of this catalyst in the synthesis of hydroperoxy alcohols.
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Page/Page column 14-16-23
(2021/07/02)
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- Oxidative carbon-carbon bond cleavage of 1,2-diols to carboxylic acids/ketones by an inorganic-ligand supported iron catalyst
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The carbon-carbon bond cleavage of 1,2-diols is an important chemical transformation. Although traditional stoichiometric and catalytic oxidation methods have been widely used for this transformation, an efficient and valuable method should be further explored from the views of reusable catalysts, less waste, and convenient procedures. Herein an inorganic-ligand supported iron catalyst (NH4)3[FeMo6O18(OH)6]·7H2O was described as a heterogeneous molecular catalyst in acetic acid for this transformation in which hydrogen peroxide was used as the terminal oxidant. Under the optimized reaction conditions, carbon-carbon bond cleavage of 1,2-diols could be achieved in almost all cases and carboxylic acids or ketones could be afforded with a high conversion rate and high selectivity. Furthermore, the catalytic system was used efficiently to degrade renewable biomass oleic acid. Mechanistic insights based on the observation of the possible intermediates and control experiments are presented.
- Chen, Weiming,Xie, Xin,Zhang, Jian,Qu, Jian,Luo, Can,Lai, Yaozhu,Jiang, Feng,Yu, Han,Wei, Yongge
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supporting information
p. 9140 - 9146
(2021/11/23)
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- FUNCTIONAL LIPID DERIVATIVES AND USES THEREOF
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The present disclosure relates to compounds, compositions, and methods for delivery of therapeutic, diagnostic, or prophylactic agents (for example, a nucleic acid).
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Page/Page column 5
(2021/11/26)
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- LIPID CONJUGATE PREPARED FROM SCAFFOLD MOIETY
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The application relates to a lipid conjugate of formula M-X1-L wherein M is a molecule of interest such as a drug moiety; X1 is a linker group such as ester, ether or carbamate; and L is a lipid scaffold represented by formula (lId): -L1-[L2(H)(X2R)]n-L3-[L4(H)(X2R)]p-L5-L6 and wherein L comprises 5 to 40 carbon atoms and 0 to 2 carbon-carbon double bonds. The lipid conjugate can be formulated in a drug delivery vehicle such as a lipid nanoparticle (LNP).
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Page/Page column 68
(2020/10/18)
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- An assay for DNA polymerase β lyase inhibitors that engage the catalytic nucleophile for binding
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DNA polymerase β (Pol β) repairs cellular DNA damage. When such damage is inflicted upon the DNA in tumor cells treated with DNA targeted antitumor agents, Pol β thus diminishes their efficacy. Accordingly, this enzyme has long been a target for antitumor therapy. Although numerous inhibitors of the lyase activity of the enzyme have been reported, none has yet proven adequate for development as a therapeutic agent. In the present study, we developed a new strategy to identify lyase inhibitors that critically engage the lyase active site primary nucleophile Lys72 as part of the binding interface. This involves a parallel evaluation of the effect of the inhibitors on the wild-type DNA polymerase β (Pol β) and Pol β modified with a lysine analogue at position 72. A model panel of five structurally diverse lyase inhibitors identified in our previous studies (only one of which has been published) with unknown modes of binding were used for testing, and one compound, cis-9,10-epoxyoctadecanoic acid, was found to have the desired characteristics. This finding was further corroborated by in silico docking, demonstrating that the predominant mode of binding of the inhibitor involves an important electrostatic interaction between the oxygen atom of the epoxy group and Nε of the main catalytic nucleophile, Lys72. The strategy, which is designed to identify compounds that engage certain structural elements of the target enzyme, could find broader application for identification of ligands with predetermined sites of binding.
- Chen, Shengxi,Cheng, Qi,Daskalova, Sasha M.,Eisenhauer, Brian M.,Fahmi, NourEddine,Feng, Xizhi,Gao, Mingxuan,Hecht, Sidney M.,Ji, Xun,Khdour, Omar M.
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- Interface infiltration regulation and control oil displacement agent and preparation method and application thereof
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The invention relates to the field of interface infiltration regulation and control oil displacement agents and surfactants, and discloses an interface infiltration regulation and control oil displacement agent and a preparation method and application thereof. The interface infiltration regulation and control oil displacement agent has a structural formula shown as a formula (I), n1 and n2 are thesame or different and are integers of 3-9 respectively, and M is Na and/or K; the oil displacement agent can improve the oil film stripping efficiency;
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Paragraph 0068-0072; 0075-0076; 0083-0085; 0088-0090
(2020/11/26)
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- Method for synthesizing 9,10-dihydroxystearic acid
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The invention discloses a method for synthesizing 9,10-dihydroxystearic acid. Firstly, hydrogen peroxide (30% by weight) is added into a four-necked flask, tungstic acid is added, the temperature is increased to 30-70 DEG C under stirring, after the tungstic acid is completely dissolved, oleic acid and acetic acid are added, then the temperature is increased to 40-80 DEG C, and a reaction is performed for 2-8 hours. The molar ratio of the oleic acid to the hydrogen peroxide is (1:1)-(1:5); the molar ratio of the oleic acid to the acetic acid is (1:0.5)-(1:3); the mass ratio of the oleic acid to the tungstic acid is 0.2%-3%. After the reaction is completed, the tungstic acid, the acetic acid and the excess hydrogen peroxide are washed away by using deionized water, then a product is dissolved in a hot organic solvent, recrystallization is performed many times to obtain the pure 9,10-dihydroxystearic acid, and the organic solvent can be recycled through reduced pressure distillation.
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Paragraph 0009; 0022-0028
(2019/07/08)
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- OXIDATIVE CLEAVAGE OF OLEFINS, EPOXIDES AND ALCOHOLS
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Provided is a process for producing a compound I comprising at least one functional group chosen in the group consisting of epoxy group, hydroxyl group and carbonyl group and by reacting a compound J comprising at least one functional group chosen in the group consisting of alkenyl group, epoxy group and hydroxyl group with an an oxidant in the presence of solid amphiphilic catalytic particles A and solid amphiphilic catalytic particles B.
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Page/Page column 24-25
(2019/02/06)
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- Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials
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A set of compounds from non-edible fat waste was prepared and their thermal behavior was studied. The fat was hydrolyzed and crystallized in a simple and robust process to yield palmitic acid-stearic acid (PA-SA) mixtures. The PA-SA mass ratios determined by GC-FID (gas chromatography-flame ionization detection) were similar to those reported for eutectic mixtures of PCMs (phase change materials). DSC (differential scanning calorimetry) results indicated that the melting and solidification temperatures were around 55 °C and 52 °C and the latent heat of the crystallized fractions measured was around 180 kJ kg-1. The thermal cycling reliability of the eutectic mixtures was also tested during 1000 melting/freezing cycles. The loss in melting and solidification enthalpies was below 14% in all mixtures showing a promising behavior for PCM applications. Additionally, the unsaturated fatty acids were recovered and transformed to threo-9,10-dihydroxystearic acid (DHSA) and some of their inorganic salts, which were analyzed by FT-IR (Fourier transform-infrared spectroscopy) and tested for the first time using the DSC technique.
- Gallart-Sirvent, Pau,Martín, Marc,Villorbina, Gemma,Balcells, Mercè,Solé, Aran,Barrenche, Camila,Cabeza, Luisa F.,Canela-Garayoa, Ramon
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p. 24133 - 24139
(2017/07/10)
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- A method for the synthesis of multi-hydroxy stearate
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The invention discloses a synthesis method of polyhydroxy stearate and application of the polyhydroxy stearate in PVC (polyvinyl chloride) resin heat stabilizers. The existing alkaline process for preparing 9,10-bis-hydroxystearic acid is complex in after-treatment, and no one has applied bis-hydroxystearate to PVC heat stabilizers. The invention is characterized in that in the polyhydroxy stearic acid synthesis, fatty acid, acetic acid and 40 wt% hydrochloric acid are added into the reaction vessel, wherein the fatty acid is one or mixture of more of oleic acid, linoleic acid and linolenic acid; in the system, the mass ratio of fatty acid to anhydrous acetic acid 30% to oxydol is 1:(0.5-2):(1-3.5); and in the reaction system, the mass ratio of anhydrous acetic acid to water is 1:(2.0-3.0). In the synthesis method, the product can be directly precipitated from the system, thereby simplifying the after-treatment.
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Paragraph 0030; 0031
(2016/12/01)
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- Process for preparing a carboxylic acid from a diol or from an epoxide by oxidative cleavage
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A process for preparing a carboxylic acid, by oxidative cleavage of at least one vicinal diol, or an epoxide, wherein the reaction is carried out in the presence of a catalyst and of an oxidizing agent and in the absence of solvent.
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Page/Page column 6
(2016/06/28)
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- PROCESS FOR PREPARING A CARBOXYLIC ACID FROM A DIOL OR FROM AN EPOXIDE BY OXIDATIVE CLEAVAGE
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A process for preparing a carboxylic acid, by oxidative cleavage of at least one vicinal diol, or an epoxide, wherein the reaction is carried out in the presence of a catalyst and of an oxidizing agent and in the absence of solvent.
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Paragraph 0082 - 0090
(2015/08/04)
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- Sustainable Process for Production of Azelaic Acid Through Oxidative Cleavage of Oleic Acid
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This work describes two sustainable methods for production and purification of azelaic acid (AA) to replace the current process of ozonolysis of oleic acid (OA). The first proceeds in two steps, coupling smooth oxidation of OA to 9,10-dihydroxystearic acid (DSA) with subsequent oxidative cleavage by sodium hypochlorite. An alternative methodology is also proposed, using a chemocatalytic system consisting of H2O2/H2WO4 for direct oxidative cleavage of the double bond of OA at 373 K. A convenient technique for separation and purification of azelaic acid is also proposed.
- Benessere, Vincenzo,Cucciolito, Maria E.,De Santis, Augusta,Di Serio, Martino,Esposito, Roberto,Ruffo, Francesco,Turco, Rosa
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p. 1701 - 1707
(2015/12/23)
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- New dicarboxylic acid type compd.
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PROBLEM TO BE SOLVED: To provide a new dicarboxylic acid type compound having a biodegrading property and safety, and showing an excellent surface activity. SOLUTION: This new dicarboxylic acid type compound is expressed by general formula (1) [wherein, CnH2n+1is linear or branched alkyl; (n) is an integer of 1 to 22; R1is 1-22C alkylene; R2is 1-22C alkyl, provided that R1and R2are each selected so that the -R1-CH-CH-R2part shows a 9-25C hydrocarbon structure; and X shows a hydrogen ion, alkali metal ion, group 2 element ion, transition element ion, group 12 element ion, aluminum ion, indium ion, tin ion, lead ion or ammonium ion]. COPYRIGHT: (C)2011,JPOandINPIT
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Paragraph 0043
(2018/10/24)
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- Structural and solubility parameter correlations of gelation abilities for dihydroxylated derivatives of long-Chain, naturally occurring fatty acids
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Creating structure-property correlations at different distance scales is one of the important challenges to the rational design of molecular gelators. Here, a series of dihydroxylated derivatives of long-chain fatty acids, derived from three naturally occurring molecules - oleic, erucic and ricinoleic acids - are investigated as gelators of a wide variety of liquids. Conclusions about what constitutes a more (or less!) efficient gelator are based upon analyses of a variety of thermal, structural, molecular modeling, and rheological results. Correlations between the manner of molecular packing in the neat solid or gel states of the gelators and Hansen solubility data from the liquids leads to the conclusion that diol stereochemistry, the number of carbon atoms separating the two hydroxyl groups, and the length of the alkanoic chains are the most important structural parameters controlling efficiency of gel formation for these gelators. Some of the diol gelators are as efficient or even more efficient than the well-known, excellent gelator, (R)-12-hydroxystearic acid; others are much worse. The ability to form extensive intermolecular H-bonding networks along the alkyl chains appears to play a key role in promoting fiber growth and, thus, gelation. In toto, the results demonstrate how the efficiency of gelation can be modulated by very small structural changes and also suggest how other structural modifications may be exploited to create efficient gelators.
- Zhang, Mohan,Selvakumar, Sermadurai,Zhang, Xinran,Sibi, Mukund P.,Weiss, Richard G.
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supporting information
p. 8530 - 8543
(2015/06/02)
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- Synthesis of a series of hydroxycarboxylic acids as standards for oxidation of nonanoic acid
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The synthesis of a series of nonanoic acids hydroxylated in terminal,ω-1,ω-2,ω-3 positions is described. These compounds will be employed as useful standards for the study of enzymatic and microbiological oxidation of nonanoic acid.
- Rajabi, Mehdi,Lanfranchi, Moreno,Campo, Federica,Panza, Luigi
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supporting information
p. 1149 - 1154
(2014/04/03)
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- Insights into gold-catalyzed synthesis of azelaic acid
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A novel green route for the synthesis of azelaic and pelargonic acid via aerobic gold-catalyzed cleavage of 9,10-dihydroxystearic acid (DSA) was investigated recently. In this study, the examination of the reaction mechanism is described. The results of the application of 18O-labeled molecular oxygen and sodium hydroxide as well as of diastereomeric pure erythro- and threo-DSA were discussed. Assumed reaction intermediates were synthesized and subjected to the same reaction conditions as with DSA. As a conclusion from the obtained data, an oxidative dehydrogenation mechanism was postulated. Additionally, the aging of the gold catalyst used under different storage conditions was explored. the Partner Organisations 2014.
- Kulik, Anna,Martin, Andreas,Pohl, Marga-Martina,Fischer, Christine,Koeckritz, Angela
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supporting information
p. 1799 - 1806
(2014/04/17)
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- Fe-catalyzed one-pot oxidative cleavage of unsaturated fatty acids into aldehydes with hydrogen peroxide and sodium periodate
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A one-pot method has been developed for the oxidative cleavage of internal alkenes into aldehydes by using 0.5mol % of the nonheme iron complex [Fe(OTf)2(mix-bpbp)] (bpbp=N,N'-bis(2-picolyl)-2,2'-bipyrrolidine) as catalyst and 1.5equivalents of hydrogen peroxide and 1equivalent of sodium periodate as oxidants. A mixture of diastereomers of the chiral bpbp ligand can be used, thereby omitting the need for resolution of its optically active components. The cleavage reaction can be performed in one pot within 20h and under ambient conditions. Addition of water after the epoxidation, acidification and subsequent pH neutralization are crucial to perform the epoxidation, hydrolysis, and subsequent diol cleavage in one pot. High aldehyde yields can be obtained for the cleavage of internal aliphatic double bonds with cis and trans configuration (86-98 %) and unsaturated fatty acids and esters (69-96 %). Good aldehyde yields are obtained in reactions of trisubstituted and terminal alkenes (62-63 %). The products can be easily isolated by a simple extraction step with an organic solvent. The presented protocol involves a lower catalyst loading than conventional methods based on Ru or Os. Also, hydrogen peroxide can be used as the oxidant in this case, which is often disproportionated by second- and third-row metals. By using only mild oxidants, overoxidation of the aldehyde to the carboxylic acid is prevented. Copyright
- Spannring, Peter,Yazerski, Vital,Bruijnincx, Pieter C. A.,Weckhuysen, Bert M.,Klein Gebbink, Robertus J. M.
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p. 15012 - 15018
(2013/11/06)
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- Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana
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Plant epoxide hydrolases (EH) form two major clades, named EH1 and EH2. To gain a better understanding of the biochemical roles of the two classes, NbEH1.1 and NbEH2.1 were isolated from Nicotiana benthamiana and StEH from potato and heterologously expressed in Escherichia coli. The purified recombinant proteins were assayed with a variety of substrates. NbEH1.1 only accepted some aromatic epoxides, and displayed the highest enzyme activity towards phenyl glycidyl ether. In contrast, NbEH2.1 displayed a broad substrate range and similar substrate specificity as StEH. The latter enzymes showed activity towards all fatty acid epoxides examined. The activity (Vmax) of NbEH1.1 towards phenyl glycidyl ether was 10 times higher than that of NbEH2.1. On the contrary, NbEH2.1 converted cis-9,10-epoxystearic acid with Vmax of 3.83 μmol min mg-1 but NbEH1.1 could not hydrolyze cis-9,10- epoxystearic acid. Expression analysis revealed that NbEH1.1 is induced by infection with tobacco mosaic virus (TMV) and wounding, whereas NbEH2.1 is present at a relatively constant level, not influenced by treatment with TMV and wounding. NbEH1.1 transcripts were present predominantly in roots, whereas NbEH2.1 mRNAs were detected primarily in leaves and stems. Overall, these two types of tobacco EH enzymes are distinguished not only by their gene expression, but also by different substrate specificities. EH1 seems not to participate in cutin biosynthesis and it may play a role in generating signals for activation of certain defence and stress responses in tobacco. However, members of the EH2 group hydrate fatty acid epoxides and may be involved in cutin monomer production in plants.
- Huang, Fong-Chin,Schwab, Wilfried
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- METHOD FOR PREPARING CARBOXYLIC ACIDS BY OXIDATIVE CLEAVAGE OF A VICINAL DIOL
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The present invention relates to a method for preparing carboxylic acids, in particular mono- and dicarboxylic acids, by oxidative cleavage of a vicinal diol. According to the invention, said method consists of reacting a vicinal diol of formula I: where: p is an integer comprised between 1 and 6; R1 and R2 are, separately: an alkyl or hydroxyl group having 1 to 12 carbon atoms;a —(CH2)n—C02M group where n, which can be identical or different in R1 and R2, is an integer comprised between 1 and 11 and M is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or an alkaline cation; or R1 and R2 jointly form an alkylene —(CH2)m- group where m is an integer comprised between 2 and 10, preferably between 2 and 6; with industrial-grade sodium hypochlorite (or bleach), in the absence of an organic solvent and without adding a catalyst, preferably at room temperature. The invention can be used for recycling natural vegetable oils.
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Paragraph 0060; 0061; 0062
(2013/06/04)
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- Cork suberin molecular structure: Stereochemistry of the C18 epoxy and vic-diol ω-hydroxyacids and α,ω-diacids analyzed by nmr
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Suberin is the biopolyester that protects the secondary tissues of plants against environmental variability and aggressions. Cork suberin is composed mostly of C18 ω-hydroxyacids and α,ω-diacids, 9,10-substituted with an unsaturation, an epoxide ring, or a vic-diol group. Although determinant for suberin macromolecular structure, the stereochemistry of these monomers is poorly studied, sometimes with contradictory results. An NMR technique was used here to assign the configuration of the 9,10-epoxy and 9,10-diol groups in C18 suberin acids, comparing the chemical shifts of diagnostic 1H and 13C signals with the ones of model compounds, before and after conversion of the vic-diol group into benzylidene acetal derivatives. The relative configuration was proved to be cis in the C18 9,10-epoxy and threo in the C18 9,10-diol suberin acids. These monomers were present in suberin probably as racemic mixtures, as shown by polarimetry. The revealed stereochemistry allows the suberin macromolecule to be built as an ordered array of midchain kinked C18 acids, reinforced by intramolecular hydrogen bonding.
- Santos, Sara,Cabral, Vanessa,Graca, Jose
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p. 7038 - 7047
(2013/08/23)
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- Safe use of a toxic compound: Heterogeneous OsO4 catalysis in a nanobrush polymer microreactor
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Putting osmium in its place: The immobilization of hazardous OsO 4 on polymer nanobrushes in a microreactor is a safe, effective, and green concept. The method allows reactions to be performed in a time- and chemical-saving manner, with little environmental impact, as compared to spill-over bulk processes. Copyright
- Basavaraju,Sharma, Siddharth,Maurya, Ram Awatar,Kim, Dong-Pyo
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p. 6735 - 6738
(2013/07/26)
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- Prilezhaev dihydroxylation of olefins in a continuous flow process
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Epoxidation of both terminal and non-terminal olefins with peroxy acids is a well-established and powerful tool in a wide variety of chemical processes. In an additional step, the epoxide can be readily converted into the corresponding trans-diol. Batch-wise scale-up, however, is often troublesome because of the thermal instability and explosive character of the peroxy acids involved. This article describes the design and semi-automated optimization of a continuous flow process and subsequent scale-up to preparative production volumes in an intrinsically safe manner. Olefins go with the flow: Prilezhaev dihydroxylation can be performed on a large scale in continuous flow microreactor systems in the oxidation of terminal and internal olefins. Major drivers for a continuous flow process include better control, improved safety, and a faster overall process, leading to a significantly higher throughput. Copyright
- Van Den Broek, Bas A. M. W.,Becker, René,K?ssl, Florian,Delville, Mari?lle M. E.,Nieuwland, Pieter J.,Koch, Kaspar,Rutjes, Floris P. J. T.
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p. 289 - 292
(2012/06/01)
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- Palm oil-based hydroxy fatty acids
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The present invention relates to an improved process for producing hydroxy fatty acids preferably dihydroxy or polyhydroxy acids from unsaturated fatty acids derived from natural oils and fats. The unsaturated fatty acids extracted from natural vegetable oils or animal fats preferably palm-based oleic acid is hydroxylated or oxidized by peracetic acid which formed in situ from a mixture of hydrogen peroxide and formic acid. The process for producing dihydroxy or polyhydroxy fatty acids according to the present invention involve less cost, easier to perform and reduced reaction time. In addition, the dihydroxy or polyhydroxy acids produced according to the present invention is non irritant and suitable to be used in production of cosmetic products.
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Page/Page column 8
(2008/06/13)
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- Palm-based hydroxy fatty acid
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The present invention relates to an improved process for producing hydroxy fatty acids preferably dihydroxy or polyhydroxy acids from unsaturated fatty acids derived from natural oils and fats. The unsaturated fatty acids extracted from natural vegetable oils or animal fats preferably palm-based oleic acid is hydroxylated or oxidized by peracetic acid which formed in situ from a mixture of hydrogen peroxide and formic acid. The process for producing dihydroxy or polyhydroxy fatty acids according to the present invention involve less cost, easier to perform and reduced reaction time. In addition, the dihydroxy or polyhydroxy acids produced according to the present invention is non irritant and suitable to be used in production of cosmetic products.
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Page/Page column 3-4
(2008/06/13)
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- NOVEL PROCESS FOR PRODUCING 1,2-DIOL
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A process for producing a 1,2-diol through the reaction of an olefin with hydrogen peroxide. The process is highly efficient and highly selective and catalyst recovery and reuse are easy. It does not use any strong acid or strong base causative of apparatus corrosion. The process for producing a 1,2-diol is characterized by reacting an olefin with hydrogen peroxide in the presence of a polymer having a sulfo group.
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- Catalytic Dihydroxylation of Olefins with Hydrogen Peroxide: An Organic-Solvent- and Metal-Free System
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Green and convenient: Olefins are oxidized to 1,2-diols in high yield with 30% H2O2 in the presence of resin-supported sulfonic acid (see scheme) under metal-free conditions without any organic solvent. The catalyst can be recycled easily and is effective for at least 10 cycles.
- Usui, Yoko,Sato, Kazuhiko,Tanaka, Masato
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p. 5623 - 5625
(2007/10/03)
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- Electroorganic synthesis 65. Anodic homocoupling of carboxylic acids derived from fatty acids
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Fatty acid derived carboxylic acids with double bonds, hydroxy-, amino-, keto-, ester- and epoxy groups are anodically coupled to dimers (Kolbe electrolysis) in 29 to 81% yield and up to a 2.5 mol scale. Problems due to the low conductivity of fatty acid salts were overcome by the use of a flow cell with a narrow electrode gap. Fatty acids with branched alkyl chains gave dimers with interesting emulsifying properties. Dimethyl hexadecanedioate, accessible from methyl azelate, could be cyclized and further converted into homomuscone and muscone in a few steps. A commercial mixture of dimeric fatty acids (C36-dicarboxylic acids) has been coupled to give C70-diesters. Acta Chemica Scandinavica 1998. Part 64: Nielsen, M. F., Batanero, B.,.
- Weiper-Idelmann, Andreas,Aus Dem Kahmen, Martin,Schaefer, Hans J.,Gockeln, Marianne
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p. 672 - 682
(2007/10/03)
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- Enantioconvergent transformation of racemic cis-dialkyl substituted epoxides to (R,R) threo diols by microsomal epoxide hydrolase catalysed hydrolysis
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Both enantiomers of (±)-9,10-epoxystearic acid (1b), cis-(±)-5,6-epoxyhexadecane (1c) and cis-(±)-11,12-epoxyhexadecan-1-ol (1d) as well as the meso cis-9,10-epoxyoctadecane (1a) undergo microsomal epoxide hydrolase catalyzed hydration at the (S) carbon to give the corresponding (R,R) threo diols in a >90 e.e. Copyright (C) 1996 Elsevier Science Ltd.
- Bellucci, Giuseppe,Chiappe, Cinzia,Cordoni, Antonio,Ingrosso, Giovanni
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p. 9089 - 9092
(2007/10/03)
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- Spicamycin derivatives and their use as anticancer agents
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Spicamycin derivative represented by the formula (I) or a salt thereof: STR1 wherein R represents specific diverse substituents, for example, a linear alkadienyl having from 11 to 13 carbon atoms, and R1 and R2 respectively represent H or OH. Examples of specific compounds are 6-[4'-N-(N'-trans,trans 2,4-tridecadienoylglycyl)spicaminyl-amino]purine, and 6-[4'-N-(N'-trans,trans-2,4 dodecadienyoly glycyl) spicaminyl-amino]purine. Comopunds according to this invention are useful as a pharmaceutical for inhibition of a tumor, for example, human colon cancer.
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- Kinetics and Mechanism of the Oxidation of Unsaturated Carboxylic Acids by Methyltributylammonium Permanganate in Methylene Chloride Solutions
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The product obtained when permanganate is reduced by unsaturated carboxylic acids under anhydrous conditions is manganese(III).The rate of reaction, which is subject to acid catalysis, exhibits a Hammet ρ value of 1.11 and inverse secondary isotope effects (kH/kD = 0.96-0.98) when the hydrogens on the double bond are replaced by deuterium.The involvement of a free-radical process is indicated by the formation of polymer during the oxidation of acrylic and methacrylic acids.The reaction is believed to be initiated by formation of an organometallic complex in which the double bond is a η2 ligand on manganese.Rearrangement of this complex results in the formation of a reactive manganate(V) cyclic diester, which undergoes a rapid (free-radical) reduction to manganese(III).
- Perez-Benito, Joaquin F.,Lee, Donald G.
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p. 3239 - 3243
(2007/10/02)
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- A facile, versatile procedure for the preparation of fatty acid esters suitable for glc or hplc analyses
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The preparation of fatty acid methyl esters for glc analyses and of various aryl esters for hplc analyses has traditionally been carried out in totally unrelated operations.This paper draws attention to the use of fatty acid-trifluoroacetic acid mixed anhydrides which may be directly and efficiently converted into either type of esters.The utility of the method was demonstrated by the preparation of series of methyl, 2-naphthyl, and vanillin fatty acid esters.The spectral characterization of some aryl fatty acid esters is recorded.
- Grossert, J. Stuart,Ratnayake, W. M. Nimal,Swee, Tiw
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p. 2617 - 2620
(2007/10/02)
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