2733-88-2Relevant academic research and scientific papers
A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids
Hamberg, Mats
, p. 489 - 494 (2021/04/19)
Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese-based Wurtz type coupling of alkyl bromides. 22-Bromo-3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)-docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid, was coupled to homologous ω-bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3-hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4-2H6]10-bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4-2H6]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)-dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)-octadecenoic acid and 15(Z)-tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.
Preparation method of nervonic acid and nervonic acid
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, (2020/07/27)
The invention discloses a preparation method of nervonic acid and nervonic acid. The preparation method comprises the following steps: preparing a Grignard reagent from 1-bromo-cis-13-docosaene, and carrying out an epoxy ring-opening reaction on the Grignard reagent, cuprous iodide and ethylene oxide to synthesize 1-hydroxy-cis-15-tetracosaene; and preparing nervonic acid by carrying out oxidationreaction on 1-hydroxy-cis-15-tetracosaene, iodobenzene acetate and TEMPO. By means of chemical synthesis, erucic acid is used as a raw material, and synthesis of nervonic acid is completed through esterification, reduction, bromination, Grignard reaction and oxidation. The method for synthesizing nervonic acid has the advantages of cheap and accessible raw materials, high yield, high product purity and the like, and is easy to operate.
Nickel-butadiene catalytic system for the cross-coupling of bromoalkanoic acids with alkyl grignard reagents: A practical and versatile method for preparing fatty acids
Iwasaki, Takanori,Higashikawa, Kiyokazu,Reddy, Vutukuri P.,Ho, Willbe W. S.,Fujimoto, Yukari,Fukase, Koichi,Terao, Jun,Kuniyasu, Hitoshi,Kambe, Nobuaki
supporting information, p. 2956 - 2960 (2013/03/28)
The knights who say Ni: A practical and convenient synthetic route to fatty acids involves the Ni-catalyzed alkyl-alkyl cross-coupling of bromoalkanoic acids and alkyl Grignard reagents in the presence of 1,3-butadiene as an additive (see scheme). Copyright
Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27
Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava
, p. 7880 - 7890 (2013/01/15)
The catalytic activity of CYP175A1 toward monooxygenation of saturated and monounsaturated fatty acids of various chain lengths (C16-C24) has been investigated to assess the enzymatic properties of this orphan thermostable cytochrome P450 enzyme. The resu
DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
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Page/Page column 18; 20-21; 27, (2008/12/07)
Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.
SINGLE-STAGE ESTERIFICATION OF OILS AND FATS
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Page/Page column 10-12, (2008/06/13)
A process for producing alkyl esters useful as biofuels and/or lubricants. An alkyl ester product produced by the process. The process comprises a single- stage reaction for esterifying a de-watered glyceride-containing feedstock with an anhydrous short chain alcohol in the presence of a basic esterification catalyst to produce a reaction product comprising alkyl esters and a reaction by-product comprising glycerol-containing substances and the catalyst-containing alcohol. The single-stage esterification reaction is conducted within a temperature and negative-pressure controllable vessel. The alkyl ester product is separated from the reaction by-product and may be further de-watered and/or purified. The catalyst-containing alcohol may be separated from the reaction by-product, de- watered and reused. The glycerol-containing substances may be separated from the reaction by-product and further purified. Useful glyceride-containing feedstocks include those prepared from plant or animal or fish materials, particularly those produced from seeds of mustard, canola, soybean, corn, cotton, flax and palm.
