2619-87-6

Upstream product

• 112-62-9 Methyl oleate 
• 112-80-1 cis-Octadecenoic acid 
• 1227205-99-3 N'-(tert-butyloxycarbonyl)octadec-(9Z)-enohydrazide 
• 122-32-7 trioleoylglycerol 

Downstream Products

• 2423-10-1 Oleic aldehyde 
• 98945-76-7 Oelsaeurealdehyd-<4-(4-nitro-benzolazo)-benzoylhydrazon> 
• 1107003-76-8 3-(4',5'-dihydroxyphenyl)-5-(heptadec-8-enyl)-1H-1,2,4-triazole 
• 1107003-69-9 3-(4'-hydroxyphenyl)-5-(heptadec-8-enyl)-1H-1,2,4-triazole 
• 1107003-60-0 3-phenyl-5-(heptadec-8-enyl)-1H-1,2,4-triazole 
• 1224476-38-3 1-[(9Z)-octadec-9-enoyl]-4-phenylsemicarbazide 
• 1227737-28-1 C₂₅H₃₈N₂O 

Relevant academic research and scientific papers

Synthesis of 5-heptadecyl- and 5-heptadec-8-enyl substituted 4-amino-1,2,4-triazole-3-thiol and 1,3,4-oxadiazole-2-thione from (Z)-octadec-9-enoic acid: preparation of Palladium(II) complexes and evaluation of their antimicrobial activity

Abstract: Two 4-amino-1,2,4-triazoles and two 1,3,4-oxadiazoles are obtained in a common synthetic route including hydrogenation-hydrazidation of (Z)-methyl octadec-9-enoate to octadecanoic hydrazide under atmospheric air. Preservation of olefinic bond in heptadec-8-enyl group is achieved by carrying out hydrazidation reaction under the presence of an argon atmosphere. The disappearance of the olefinic bond is detected by physical data, IR, 1H, and13C NMR spectroscopy. New palladium complexes derived from 4-amino-5-heptadecyl-1,2,4-triazole-3-thiol and 5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione are obtained and characterized by elemental analysis (solid state), IR, 1H, 13C NMR spectroscopy, XRD, and XPS. These resulting metallic entities are also identified in solution based in mass spectrometry (MS-ESI) experiments. Most compounds and their palladium(II) complexes are tested in vitro against Gram-positive, Gram-negative bacteria, and fungi, some of them showed variable activity. Graphic abstract: [Figure not available: see fulltext.].

Cyclocondensation between fatty acid hydrazides and 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones: Introducing a trifluoromethylated head onto fatty acid moieties

This paper reports the regioselective synthesis of new trifluoromethylated lipid derivatives, namely, 1-(5-hydroxy-5-trifluoromethyl-3-alkyl-4,5-dihydro-1H-pyrazol-1-yl)alkan-1-ones, through cyclocondensation reactions between a series of fatty hydrazides (palmitoyl, stearoyl, and oleoyl hydrazides) obtained from fatty acids from renewable resources (1,1,1-trifluoro-4-alkoxy-3-alken-2-ones [F3CC(O)CH?C(R1)OR, where R1 = H and R?Et; R1 = –(CH2)6CH3, –(CH2)6CH3, –(CH2)8CH3, –(CH2)9CH3, –(CH2)10CH3, –(CH2)12CH3, –(CH2)2Ph], and R?Me). Experimental observations showed that the lipophilic characteristic of 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazoles (5–7) prevent the acid catalyzed dehydration to aromatization of 1H-pyrazole ring, although in some cyclocondensations a proportion of the aromatic derivative 1-(5-trifluoromethyl-3-alkyl-1H-pyrazol-1-yl)alkan-1-one was obtained. All products were characterized using multinuclear (1H, 13C, 19F) NMR spectroscopy.

Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists

The transient receptor potential vanilloid type-2 (TRPV2) protein is a nonselective Ca2+ permeable channel member of the TRPV subfamily, still considered an orphan TRP channel due to the scarcity of available selective and potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure-activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain fatty acid ethanolamides or primary amides acting as TRPV2 antagonists. Both synthetic and endogenous antagonists exhibited differential inhibition against known TRPV2 agonists characterized by distinct kinetic profiles. These findings represent the first example of both synthetic and naturally occurring TRPV2 modulators with efficacy in the submicromolar/low-micromolar range, which will be useful for clarifying the physiopathological roles of this receptor, its regulation, and its targeting in pathological conditions.

Synthesis and antimicrobial studies of 5-n-alkyl-1,3,4-oxadiazole-2-thiol derivatives from fatty acids

The novel 5-N-alkyl-1,3,4-oxadiazole-2-thiol derivatives have been synthesized by esterification of fatty acid followed by reaction the ester with hydrazine hydrate. The acid hydrazide was converted to 1,3,4-oxadiazole by ring closure mechanism. The synthesized compounds have been characterized by physical (melting point and TLC) and spectral (IR, 1H NMR and mass) data. All the compounds were screened for their antimicrobial activity. The compounds 3F1 & 3F4 showed good inhibition activity against all four types of bacteria; while compound 3F2 & 3F3 shown moderate activity.

Involvement of reactive oxygen species in the oleoylethanolamide effects and its pyrazonilic analogue in melanoma cells

The search for more substances that effectively fight melanoma is extremely important, because of its aggressive nature. In this sense, the molecular hybridization is a promising strategy. The aim of this work is to evaluate whether the antiproliferative effect of the endocannabinoid oleoylethanolamide can be improved with the addition of a trifluoromethylated pyrazolinic nucleus on its structure in B16F10 cell line. The pyrazolinic analog was named oleoyl pyrazoline. We also compared the effects of oleoylethanolamide and that of the classic endocannabinoid anandamide (AEA). The cell viability was evaluated by MTT assay, the intracellular reactive oxygen species generation by fluorimetry, and apoptosis/necrosis by fluorescent microscopy. Also, α-tocopherol antioxidant was used to evaluate the involvement of reactive oxygen species in the cellular response. Although the effects of AEA occur in smaller concentrations, the results show that the effects of AEA and oleoylethanolamide were similar. The results showed a decrease in cell viability, induction of apoptosis and necrosis, and increased generation of reactive oxygen species by the oleoylethanolamide, while the oleoyl pyrazoline increased cell proliferation and decreased reactive oxygen species. Additionally, the effects of oleoylethanolamide in cell viability were decreased by inhibiting the generation of reactive oxygen species by α-tocopherol. Therefore, it is possible to suggest the involvement of reactive oxygen species in the effect of oleoylethanolamide in the B16F10 cells. Considering the great need to find substances that can fight melanoma and the lack of greater elucidation in the action mechanisms of cannabinoids and their analogs, this work provides important new information that could serve as reference to other studies.

A METHOD TO PRODUCE HYDRAZIDE

A method to produce hydrazide from triacylglycerol, the method includes steps of mixing vegetable oil with an organic solvent in a reactor forming a mixture, adding hydrazinemonohydrate into the mixture, stirring the mixture, adding catalyst, stirring the mixture to form hydrazide and separating the hydrazide from the mixture. Most illustrative drawing:

Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones

Doxorubicin N-acylhydrazones derived from saturated, unsaturated and terpene-terminated fatty acids were tested for anticancer activity in cells of human HL-60 leukaemia, 518A2 melanoma, MCF-7/Topo breast and KB-V1/Vbl cervix carcinomas. In the latter, the N-heptadecanoyl hydrazone was more cytotoxic than its unsaturated C18-fatty acyl analogues and even three times more than doxorubicin. The (menthoxycarbonyl)undecanoyl hydrazone was twice as active as doxorubicin in these multidrug resistant KB-V1/Vbl and in the 518A2 cells and also more efficacious in KB-V1 and MCF-7 cells that had been desensitised for doxorubicin. All hydrazones induced apoptosis albeit by slightly different mechanisms. While apoptosis induction by the menthoxymalonyl hydrazone was characterized by an upfront increase in caspase-8 activity, all other hydrazones elicited a hike in caspase-9 activity. Treatment of HL-60 and 518A2 cells with doxorubicin or its heptadecanoyl, linolenoyl, (menthoxycarbonyl)undecanoyl or menthoxymalonyl hydrazones also led to diverging increases of the ratio of bax to bcl-2 mRNA expression, of reactive oxygen species and of mitochondrial membrane damage.

Synthesis and cyclisation of 1,4-disubstituted semicarbazides

Semicarbazides, besides possessing medicinal properties, also find wide applications in agriculture and industry. We report in this article the synthesis of the four 1,4-disubstituted semicarbazides: 1-cinnamoyl-4-phenyl semicarbazide (1), 1-oleyl-4-phenyl semicarbazides (2), 1,1',1''-tricitryl-4,4', 4''-triphenyl semicarbazide (3) and 1-benzoyl-4-phenyl semicarbazide (4), by the condensation of four different hydrazides: cinnamic acid hydrazide (5), oleic acid hydrazide (6), citric acid hydrazide (7) and benzoic acid hydrazide (8). The acid hydrazides were prepared by the condensation of four different acids with phenyl isocyanate. The semicarbazides were also subjected to acid catalysed intramolecular cyclisation. The cyclisation of (1) and (2) afforded substituted 1,3,4-oxadizoles: 2-cinnamoyl-5-aminophenyl 1,3,4-oxadizoles (9) and 2-oleyl-5-aminophenl 1,3,4-oxadizoles (10), respectively, in high yield, while no cyclisation occurred in the cases of (3) and (4). The products in each case have been identified on the basis of melting points and IR spectral studies.

Preparation of saturated and unsaturated fatty acid hydrazides and long chain C-glycoside ketohydrazones

A method is described to prepare both saturated and unsaturated fatty acid acyl hydrazides using a lipase as a catalyst. Hydrazides were generated from fatty acid methyl esters as well as directly from vegetable oils, and an organic co-solvent was not needed to maintain the integrity of the unsaturated fatty acids. Both C. antarctica lipase immobilized on acrylic resin and immobilized M. miehei lipase were used to catalyze the reaction, and they provided the desired acyl hydrazides with similar yields of 82.8% and 84.6%, respectively. Analysis of the products by MALDI-TOF-MS and GC-MS fragmentation pathways shows pure products free of starting methyl esters or triacylglycerols. These hydrazide molecules have been used, in conjunction with carbohydrate C-glycoside ketones, to prepare long chain C-glycoside ketohydrazones. This preparation does not require protecting groups or anomeric activation, and various C-glycoside ketohydrazones that retain the closed ring conformation of the parent sugars are described. These compounds have potential as renewable, sugar-based detergents in which the sugar moiety serves as the polar head group while the hydrazide alkyl chain is the non-polar component. The Royal Society of Chemistry 2010.

Inhibitors of oleamide hydrolase

Inhibitors of oleamide hydrolase, responsible for the hydrolysis of an endogenous sleep-inducing lipid (1, cis-9-octadecenamide) were designed and synthesized. The most potent inhibitors possess an electrophilic carbonyl group capable of reversibly forming a (thio) hemiacetal or (thio) hemiketal to mimic the transition state of a serine or cysteine protease catalyzed reaction. In particular, the tight binding alpha -keto ethyl ester 8 (1.4 nM) and the trifluoromethyl ketone inhibitor 12 (1.2 nM) were found to have exceptional inhibitory activity. In addition to the inhibitory activity, some of the inhibitors displayed agonist activity which resulted in the induction of sleep in laboratory animals.