105517-82-6Relevant articles and documents
RETINAL BIOAVAILABILITY OF SYNTHETIC VERY-LONG-CHAIN POLYUNSATURATED FATTY ACIDS
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, (2022/01/05)
The rare non-dietary very-long-chain polyunsaturated fatty acids (VLC-PUFAs) uniquely found in retina and a few other tissues play a clinically significant role in retinal degeneration and development, but their physiological and interventional research has been hampered by scarcity of pure VLC-PUFAs. Disclosed herein are methods of making fatty acids, including VLC-PUFAs, and methods of using these fatty acids in, for example, treating eye disorders and supplementing the diet of a female subject who is pregnant, desiring to become pregnant, or lactating. Also disclosed are compositions containing fatty acids and methods of making and using same. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
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.
SYNTHESIS AND USE OF OMEGA-3 AND OMEGA-6 VERY LONG CHAIN POLYUNSATURATED FATTY ACIDS (VLC-PUFA)
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, (2011/05/11)
The invention provides methods of synthesizing omega-3 and omega-6 very long chain polyunsaturated fatty acids (VLC- PUFAs, C28-C42:4,5 and 6), analogs and derivatives thereof, pharmaceutical compositions containing these isolated VLC-PUFA compounds and therapeutic uses therefor.