1422-26-0Relevant academic research and scientific papers
Synthesis of Both the Enantiomers of Phoracantholide I; A Defensive Secretion of the Eucarypt Longicorn (Phoracantha synonyma), Employing Microbial Asymmetric Reduction with Immobilized Baker's Yeast
Naoshima, Yoshinobu,Hasegawa, Hidenobu,Nishiyama, Tadashi,Nakamura, Akihiro
, p. 608 - 610 (1989)
Highly optically pure (R)- and (S)-phoracantholide I were synthesized in relatively short steps starting from diethyl 3-oxoglutarate by means of a microbial asymmetric reduction of the intermediate keto acid with immobilized baker's yeast entrapped in gels of κ-carrageenan.
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.
Taste modifiers
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Page/Page column 8-9, (2016/11/21)
A method of modifying the taste of a consumable, comprising adding to a consumable base at least one compound of the formula I in which (a) A is selected from the moieties (b) n is from 0-7, such that X is absent or a linear alkylene group in which n is from 1-7; and (c) Z is absent and Y is a moiety selected from the groups —CHO, or —CH2OH; or (d) Z is present and is a C1-7 linear alkane, and Y is selected from —CHOH, —CO, or —COC(CH3)O. The result is a consumable with enhanced mouthfeel and/or creaminess.
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.
Oxidation catalytic system and oxidation process using the same
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, (2008/06/13)
A substrate (e.g., a cycloalkane, a polycyclic hydrocarbon, an aromatic compound having a methyl group or methylene group adjacent to an aromatic ring) is oxidized with oxygen in the presence of an oxidation catalyst comprising an imide compound of the following formula (1) (e.g., N-hydroxyphthalimide), and a co-catalyst (except phosphovanadomolybdic acid) containing an element selected from the group consisting of Group 2A elements of the Periodic Table of Elements, transition metals (Group 3A to 7A elements, Group 8 elements, Group 1B elements and Group 2B elements of the Periodic Table of Elements) and Group 3B elements of the Periodic Table of Elements, for the formation of an oxide (e.g., a ketone, an alcohol, a carboxylic acid): STR1 wherein R1 and R2 represent a substituent such as a hydrogen atom or a halogen atom, or R1 and R2 may together form a double bond or an aromatic or nonaromatic 5- to 12-membered ring, X is O or OH, and n is 1 to 3.
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.
A New and Efficient Approach to Macrocyclic Keto Lactones
Karim, Mohammad R.,Sampson, Paul
, p. 598 - 605 (2007/10/02)
A new and efficient method for macrolactonization has been developed.The intramolecular nucleophilic displacement of chloride from the highly electrophilic α-chloro ketone moiety in 15 by a remote carboxylate nucleophile resulted in the clean formation of the 11-membered keto lactone 1.Relatively high substrate concentrations (up to 18 mM) could be employed without formation of dimeric or oligomeric byproducts.The slow mixing of substrate and base was not required.This macrolactonization reaction was studied in various solvents at a number of substrate concentrations and reaction temperatures in order to evaluate its scope and limitations.A low-temperature Ti(III) ion/peroxide induced radical addition reaction has been developed.The lowering of the reaction temperature from 0 deg C to -78 deg C consistently afforded a dramatic increase in product yield from such reactions.This lowering of the reaction temperature proved essential when the highly functionalized acetoxymethyl vinyl ketone was employed as the radical acceptor.
