927-38-8Relevant articles and documents
10(S)-hydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid
Kim, Hakryul,Gardner, Harold W.,Hou, Ching T.
, p. 95 - 99 (2000)
The new microbial isolate Pseudomonas aeruginosa (PR3) has been reported to produce from oleic acid a new compound, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD), with 10-hydroxy-8-octadecenoic acid (HOD) being a probable intermediate. The production of DOD involves the introduction of two hydroxyl groups at carbon numbers 7 and 10, and a rearrangement of the double bond from carbons 9-10 to 8-9. It has been shown that the 8-9 unsaturation of HOD was possibly in the cis configuration. Now we report that the rearranged double bond of HOD is trans rather than cis, as determined by spectral data. Also, it was found that the 10-hydroxyl was in the S-configuration as determined by gas chromatographic separation of R- and S-isomers after preparation of the (-)-menthoxycarbonyl derivative of the hydroxyl group followed by oxidative cleavage of the double bond and methyl esterification. This latter result coincides with our recent finding that the main final product, DOD, is in the 7(S),10(S)-dihydroxy configuration. In addition, a minor isomer of HOD (about 3%) with the 10(R)-hydroxyl configuration was also detected. From the data obtained herein, we concluded that 10(S)-hydroxy-8(E)-octadecenoic acid is the probable intermediate in the bioconversion of oleic acid to 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid by PR3.
Production of 10(S)-hydroxy-8(E)-octadecenoic acid mono-estolides by lipases in non-aqueous media
Martin-Arjol,Busquets,Manresa
, p. 224 - 230 (2013/05/22)
In this study, Novozym 435, a lipase B from Candida antarctica, was used for fatty acid polymerization. For the first time, an apolar reaction media, n-hexane, was used to synthesize in vitro estolides from trans-hydroxy-fatty acids derived from the biotransformation of oleic acid by Pseudomonas aeruginosa 42A2 NCIMB 40045. We studied the effects of the substrate, the enzyme ratio, the enzyme stability and the reusability of the biocatalyst. To determine the structure of the oligomers formed, both liquid chromatography mass spectrometry and MALDI-TOF mass spectrometry, with a DHB matrix neutralized with lithium hydroxide, were used to obtain simpler mass spectra. Estolides composed of two units of (10S)-HOME were synthesized with a reaction yield of 30%. Finally, various lipases were screened, and another apolar organic solvent, iso-octane, was assayed to try to increase the reaction yield.
Natural Estolides Produced by Pseudomonas sp. 42A2 Grown on Oleic Acid: Production and Characterization
Pelaez,Orellana,Marques,Busquets,Guerrero,Manresa
, p. 859 - 866 (2007/10/03)
Estolides are a group of FA polyesters resulting from ester bond formation between a hydroxyi or olefinic group of one FA and the terminal carboxyl group of a second FA. These products are commonly found in trace amounts, forming tetraglycerides in several oil seed plants, and have been produced by acid clay and enzymatic catalysis in vitro. In this study, natural estolides produced by a bacterial culture are presented for the first time. Pseudomonas sp. 42A2 produced (E)-10-hydroxy-8-octadecenoic acid and (E)-7,10-dihydroxy-8-octadecenoic acid when grown on oleic acid. It is suggested that these FA were polymerized in culture by a lipase produced by the bacterial strain, resulting in a mixture of estolides. These compounds amounted to 3.8 g/L after 72 h of incubation. LC-MS analysis indicated that the types of estolides formed were dimers (m/z 560-610), trimers (m/z 845-906), tetramers (m/z 1122-1202), pentamers (m/z 1328-1424), and hexarners (m/z 1554-1788), with a relative abundance of 27.5, 19.4, 15, 9.7, and 11%, respectively. This is the first report in which hexamers were detected in a bacterial culture.
