2390-09-2Relevant articles and documents
Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach
Hess, Sandra K.,Schunck, Natalie S.,Goldbach, Verena,Ewe, Daniela,Kroth, Peter G.,Mecking, Stefan
supporting information, p. 13487 - 13491 (2017/10/05)
A dual catalysis approach enables selective functionalization of unconventional feedstocks composed of complex fatty acid mixtures with highly unsaturated portions like eicosapentaenoate (20:5) along with monounsaturated compounds. The degree of unsaturation is unified by selective heterogeneous hydrogenation on Pd/γ-Al2O3, complemented by effective activation to a homogeneous carbonylation catalyst [(dtbpx)PdH(L)]+ by addition of diprotonated diphosphine (dtbpxH2)(OTf)2. By this one-pot approach, neat 20:5 as a model substrate is hydrogenated to up to 80% to the monounsaturated analogue (20:1), this is functionalized to the desired C21 α,ω-diester building block with a linear selectivity of over 90%. This catalytic approach is demonstrated to be suitable for crude microalgae oil from Phaeodactylum tricornutum genetically engineered for this purpose, as well as tall oil, an abundant waste material. Both substrates were fully converted with an overall selectivity to the linear α,ω-diester of up to 75%.
Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27
Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava
, p. 7880 - 7890 (2013/01/15)
The catalytic activity of CYP175A1 toward monooxygenation of saturated and monounsaturated fatty acids of various chain lengths (C16-C24) has been investigated to assess the enzymatic properties of this orphan thermostable cytochrome P450 enzyme. The resu
Three new fatty acid esters from the mushroom Boletus pseudocalopus
Kim, Ki Hyun,Choi, Sang Un,Lee, Kang Ro
, p. 593 - 599 (2012/09/10)
A bioassay-guided fractionation and chemical investigation of a MeOH extract of the Korean wild mushroom Boletus pseudocalopus resulted in the identification of three new fatty acid esters, named calopusins A-C (1-3), along with two known fatty acid methyl esters (4-5). These new compounds are structurally unique fatty acid esters with a 2,3-butanediol moiety. Their structures were elucidated through 1D- and 2D-NMR spectroscopic data and GC-MS analysis as well as a modified Mosher's method. The new compounds 1-3 showed significant inhibitory activity against the proliferation of the tested cancer cell lines with IC50 values in the range 2.77-12.51 μM. AOCS 2011.
Efficient synthesis of unsaturated 1-monoacyl glycerols for in meso crystallization of membrane proteins
Fu, Yu,Weng, Yue,Hong, Wen-Xu,Zhang, Qinghai
, p. 809 - 812 (2011/06/21)
A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization. Georg Thieme Verlag Stuttgart.
A novel triacylglycerol from a cytotoxic extract of a red sea marine fungus
Nawwar,Hussein, Sahar A.,Hashim, Amani N.,Barakat, Heba H.,Mernitz, Gudrun,Cuypers, Beate,Linscheid, Michael,Lindequist, Ulrike
, p. 325 - 332 (2013/06/04)
INVESTIGATION of the CH2Cl2 extract of a taxonomically ....... unidentified anamorphic fungus strain MF 014, has yielded the glycerol triester, 1,3-O-bis-Z-11-eicosenoyl 2-O-Z-9, Z-12-nonadecadienoyl glycerol. The structure of this novel metabolite was established on the basis of extensive 1D- and 2D-NMR spectroscopic studies as well as on mass spectrometric analysis. The extract exhibited in vitro cytotoxic activity against human amniotic epithelial cells (FL cells) in the neutral red assay.
DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
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Page/Page column 18; 21-22; 29, (2008/12/07)
Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.
Pheromones via organoboranes: Part IV - Synthesis of (Z)-9-tricosene (Muscalure)
Dhillon, Ranjit S.,Singh, Rupinder P.,Singh, Jasvinder
, p. 718 - 721 (2007/10/03)
Synthesis of (Z)-9-tricosene (muscalure) (9) is reported starting from oleyl alcohol by two carbon homologation via dianion of phenoxyacetic acid followed by reduction (LAH), oxidation (PCC) and Grignard reaction.
