506-51-4Relevant academic research and scientific papers
Identification of β-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica
Busta, Lucas,Budke, Jessica M.,Jetter, Reinhard
, p. 38 - 49 (2015/12/01)
The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography-mass spectrometry (GC-MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC-MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by β-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C42 to C50 and the most prominent homolog being C46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C40-C52 also dominated by the C46 homolog. The β-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed.
METHOD FOR THE PRODUCTION OF PRIMARY LONG-CHAIN ALCOHOLS
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Page/Page column 11-12, (2010/02/15)
The invention relates to a method for the production of linear long-chain alcohols with 20 to 40 carbon atoms by means of a growth reaction with ethylene on aluminium compounds.
The synthesis of a single enantiomer of a major α-mycolic acid of M. tuberculosis
Al Dulayymi, Juma'a R.,Baird, Mark S.,Roberts, Evan
, p. 11939 - 11951 (2007/10/03)
We report a synthesis of a single enantiomer of a mycolic acid from Mycobacterium tuberculosis containing a di-cis-cyclopropane. The method can be simply varied to modify the chain lengths or the absolute stereochemistry of either cyclopropane.
Organoboranes for synthesis. 13. Simple, efficient syntheses of long-chain alcohols and carboxylic acids
Brown, Herbert C.,Iyer, Ramakrishnan R.,Bhat, Narayan G.,Racherla, Uday S.,Brown, Charles A.
, p. 9187 - 9194 (2007/10/02)
General, convenient and simple syntheses of long straight chain alcohols and carboxylic acids were developed utilizing organoborane chemistry. One of the methods entails the thermal isomerization of long-chain alkyldicyclohexylboranes, followed by oxidation. An alternative procedure for the preparation of long-chain alcohols involves the KAPA isomerization of internal alkynes to the terminal derivative, followed by dihydroboration with 9-BBN and oxidation. Alternatively, the terminal alkyne can be oxidised directly to the carboxylic acid. In another strategy, the C30-alcohol triaxontanol was prepared by employing high pressure carbonylation of a borane intermediate.
Synthesis of even C24-C30 primary normal aliphatic alcohols from cyclododecanone
Zakharkin, L. I.,Churilova, I. M.,Anikina, E. V.
, p. 65 - 67 (2007/10/02)
A simple method has been developed for the oxidation of cyclododecanone by sodium persulfate in an aqueous methanol solution of sulfuric acid to give 12-hydroxydodecanoic acid, which upon treatment with HBr in acetic acid gives 12-bromododecanoic acid with RMgX, where R=C12H25, C14H29, C16H33, and C18H37 in THF in the presence of Li2CuCl4 and subsequent reduction of the salts of the alkanecarboxylic acids by LiAlH4 give primary even normal C24-C30 alcohols.
A New Synthesis of Long Chain Acid Esters and Carbinols
Rao, S. Jagadishwar,Bhalerao, U. T.,Tilak, B. D.
, p. 208 - 211 (2007/10/02)
A versatile synthesis of difficulty accessible long chain acid esters and carbinols is described.The synthesis involves acylations at 2- and 5-positions of thiophene.Thioketalation of the resulting ketoesters followed by Raney nickel desulfurization yield acid esters which on LAH reduction give the corresponding carbinols.
