1422-26-0Relevant articles and documents
Structure of a new antimicrobial unsaturated fatty acid from Sm. kitasatoensis NU 23 1
Omura,Imai,Takeshima,Nakagawa
, p. 3139 - 3143 (1976)
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Synthesis of Both Enantiomers of Phoracantholide I, a Defensive Secretion of the Eucarypt Longicorn, Employing Asymmetric Reduction with Immobilized Baker's Yeast
Naoshima, Yoshinobu,Hasegawa, Hidenobu
, p. 2379 - 2382 (1987)
Highly enantiomerically pure (R)- and (S)-phoracantholide I were synthesized in relatively short steps starting from diethyl 3-oxoglutarate by means of an asymmetric reduction of the intermediate keto acid with immobilized baker's yeast.The asymmetric reduction with the immobilized baker's yeast gave greater facilities compared with the analogous reaction with free baker's yeast.
Hydrogen and trimethylsilyl transfers during EI mass spectral fragmentation of hydroxycarboxylic and oxocarboxylic acid trimethylsilyl derivatives
Rontani, Jean-Franois,Aubert, Claude
, p. 66 - 75 (2015/02/19)
This paper, describing electron ionization mass spectral fragmentation of some hydroxycarboxylic and oxocarboxylic acid trimethylsilyl derivatives, focuses on the formation of fragment ions resulting from the interactions between the two functionalities of these compounds. These interactions result in the formation of fragment ions at [CH2=C(OTMS)2]+·, [CH2=CHC(OTMS)=OTMS]+, [M-31]+, [M-105]+, and [M-RCHO]+· in the case of hydroxycarboxylic acid trimethylsilyl derivatives of formula RCHOTMS(CH2)nCOOTMS and at [RC(OTMS)=CH2]+·, [RC(=OTMS)CH=CH2]+, and [M - RC(=O)CH2]+ in the case of oxocarboxylic acid trimethylsilyl esters of formula RC(=O)(CH2)nCOOTMS. Some of these fragmentations appeared to be sufficiently specific to be used to characterize these compounds. Several fragmentation pathways involving trimethylsilyl and hydrogen transfers were proposed to explain the formation of these different fragment ions and were substantiated by deuterium labeling.
Reactions of Dioxiranes with Selected Oleochemicals
Sonnet, P. E.,Lankin, M. E.,McNeill, G. P.
, p. 199 - 204 (2007/10/02)
Reaction of fatty acids with dimethyldioxirane in acetone produces ketoacids in 9-12percent yields in which the ketone carbonyl is distributed along the fatty chain.The n-1 position appears to be preferred.Lactones of hydroxy fatty acids are oxidized by this reagent, but in low yields, to the corresponding ketoacids.Biphasic epoxidations with methylethyldioxirane in 2-butanone were conducted with methyl oleate and methyl ricinoleate to give the corresponding epoxides in high yield, and olive oil and tallow were cleanly epoxidized by this procedure as well.KEY WORDS: Chain functionalization, dioxirane, epoxidation, oleic acid, ricinoleic acid, tallow.