64713-66-2Relevant academic research and scientific papers
Identification of (E)-11-hydroxy-9-octadecenoic acid and (E)-9-hydroxy-10-octadecenoic acid by biotransformation of Oleic acid by pseudomonas sp. 32T3
Rodriguez,Espuny,Manresa,Guerrero
, p. 593 - 597 (2001)
Pseudomonas sp. 32T3, a newly identified strain originally isolated from a vegetable oil-contaminated soil, produces three monohydroxy acids-(E)-11-hydroxy-9-octadecenoic acid, (E)-10-hydroxy-8-octadecenoic acid, and (E)-9-hydroxy-10-octadecenoic acid-as
A mechanistic study of oleate autoxidation: Competing peroxyl H-atom abstraction and rearrangement
Porter, Ned A.,Mills, Karen A.,Carter, Randall L.
, p. 6690 - 6696 (2007/10/02)
The mechanism of methyl oleate autoxidation was investigated. HPLC techniques were developed to analyze the products of autoxidation (hydroperoxides and the corresponding alcohols). The alcohols could be completely resolved by normal-phase chromatography, six products being characterized having oxygen substitution and double position as follows: 11-OOH-trans-△9-10, 11-OOH-cis-△9-10, 10-OOH-trans-△8-9, 9-OOH-trans-10-11, 8-OOH-trans-△9-10, 8-OOH-cis-△9-10 As the hydrogen atom donor concentration of the medium of autoxidation is increased, increased 11-cis, 8-cis, 9-trans, and 10-trans hydroperoxides and decreased 11-trans and 8-trans hydroperoxides were obtained, consistent with a mechanism in which peroxyl H-atom abstraction and [2,3] allylperoxyl rearrangement are in competition, An iterative computer kinetic analysis was developed which modeled the oleate autoxidation mechanism, and. rearrangement rate constants were determined. Allylperoxyl radicals undergo rearrangement with different rates depending on the geometry of the allylperoxyl.
Synthesis of Cyclic Peroxides from Methyl Oleate
Bascetta, Emanuele,Gunstone, Frank D.
, p. 2207 - 2216 (2007/10/02)
A mixture of -9(10)-hydroxyoctadec-10(8)-enoates (3a) and (3b), produced by the photosensitised oxidation of methyl oleate, is a suitable substrate for the synthesis of substituted dioxolanes.Peroxymercuriation of (3) followed by hydrogenodemercuriation affords 3-(6-methoxycarbonylhexyl)-5-octyl- and 5-heptyl-3-(7-methoxycarbonylheptyl)-1,2-dioxolanes (5a) and(5b) in good yield (45-70percent).Peroxymercuriation followed by bromodemercuriation yields the corresponding bromo substituted cyclic peroxides (epidioxides) (9a) and (9b) in higher yield (95percent).Direct bromination of the allylic hydroperoxides (3a) and (3b) affords the same bromo substituted cyclic peroxides (9a) and (9b) in almost quantitative yield, presumably via a bromonium ion intermediate.
