7212-53-5Relevant articles and documents
Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca
Dickschat, Jeroen S.,Bruns, Hilke,Riclea, Ramona
supporting information; experimental part, p. 1697 - 1712 (2012/02/04)
The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω-1)-branched, (ω-2)-branched, α-and (ω-1)-branched, γ-and (ω-1)-branched, γ-and (ω-2)-branched, and γ-and (ω-3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [ 2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM).
Studies related to fatty acid desaturation. Part I: Preparation of methyl-substituted nonanols, nonyl bromides and total synthesis of new branched oleic acids
Genard, S.,Patin, H.
, p. 397 - 406 (2007/10/02)
Convenient pathways for the synthesis of seven structurally defined isomers of methyl-nonanols and methyl-nonylbromides are described.These synthons are used to perform Wittig reactions between convenient phosphoranes and aldehydes in order to obtain seven new octadecenoic acids bearing a methyl grouping on carbons 11 to 17. branched nonan-1-ols / branched 1-nonylbromides / Wittig reactions / methyl 9-bromononanoate / methyl 8-formyloctanoate / methyl 11 or 17-methyloctadec-9-enoates
SYNTHETIC INVESTIGATIONS INTO INSECT-ATTRACTING SUBSTANCES (SEX ATTRACTANTS). IV. SYNTHESIS OF 14-METHYL-8-cis-HEXADECENAL AND 14-METHYL-8-trans-HEXADECENAL, COMPONENTS OF THE SEX PHEROMONE OF THE DERMESTID BEETLE Trogoderma granarium EVERTS
Kovalev, B. G.,Rastegaeva, V. M.
, p. 44 - 47 (2007/10/02)
14-Methyl-8-hexadecyn-1-ol was obtained by the alkylation of 7-methyl-1-nonyne with heptamethylene chlorohydrin.Its hydrogenation in the presence of colloidal nickel catalyst was used for the synthesis of 14-methyl-8-cis-hexadecen-1-ol, and reduction with lithium aluminum hydride was used for the synthesis of 14-methyl-8-trans-hexadecen-1-ol.Both ethylenic alcohols were converted by oxidation into the corresponding aldehydes, which are the main components of the sex pheromone of the dermestid beetle.
