Oxidation of oleic acid

HOOO(CH2)7COOH. Colourless plates, m.p. lOfi C. Made by the oxidation of oleic acid with ozones. 

Oxidation of oleic acid to 10-hydroxyoctadecanoic acid by a gram-positive bacterium was described with a transformation yield of 65% at a concentration of 50 g oleic acid after 72 h in a medium containing Tween 80 [232]. The hydroxy fatty acid can be converted to 4-dodecanolide, an important coconut-fruity like lactone, by -oxidation with yeasts, affording a total lactone yield of about 20% from oleic acid [222, 232]. 

Which enzymes are involved in the oxidation of oleic acid to acetyl-CoA ... 

This resembles the results obtained for the oxidation of oleic acid. Further, the force-area curves of the oxidized ergosterol, lumisterol, and supra-sterol were nearly identical, with limiting areas of 60 A. per molecule, compared with 37.5 A. for ergosterol itself. 

Olefin— viC diol in aqueous medium. Unsaturated fatty acids are convertible by permanganate oxidation in alkaline solution into vic-diols in high yield. G. M. Robinson and R. Robinson briefly report oxidation of oleic acid in 300 parts of water and one third part of potassium hydroxide at 0° by gradual addition of 0.5 N... 

Derivation By the oxidation of nonyl alcohol or nonyl aldehyde by the oxidation of oleic acid, especially by ozone. 

Derivation Oxidation of oleic acid with nitric acid. 

The oxidation of unsaturated fatty acids such as oleic acid requires additional enzymes. They are needed because, unlike the trans double bonds introduced during /1-oxidation, the double bonds of most naturally occurring unsaturated fatty acids have a cis configuration. The enzyme enoyl-CoA isomerase converts the cis-/ , ydouble bond to a trans-a,fS double bond. The /3-oxidation of oleic acid is illustrated in Figure 12A. 

Swem showed that the permanganate oxidation of oleic acid (245) was pH dependent. Earlier, Lapworth and Mottram oxidized oleic acid to 9,10-dihydroxy stearic acid, 246,344 jp essentially quantitative yield by what might be considered standard conditions for hydroxylation 0.1% oleic acid, no more than 1% KMnOq, short reaction time (5 min), slight excess of alkali and a reaction temperature of 0-10°C.344 Swern found that... 

The conversion of a monounsaturated fatty acid to acetyl-GoA requires a reaction that is not encountered in the oxidation of saturated acids, a cis-trans isomerization (Figure 21.9). Successive rounds of P-oxidation of oleic acid (18 1) provide an example of these reactions. The process of P-oxidation gives rise to unsaturated fatty acids in which the double bond is in the trans arrangement, whereas the double bonds in most naturally occurring fatty acids are in the cis arrangement. In the case of oleic acid, there is a cis double bond between carbons 9 and 10. Three rounds of P-oxidation produce a 12-carbon unsaturated fatty acid with a cis double bond between carbons 3 and 4. The hydratase of the P-oxidation cycle requires a trans double bond between carbon atoms 2 and 3 as a substrate. A cis-trans isomerase produces a trans double bond between carbons 2 and 3 from the cis double bond between carbons 3 and 4. From this point forward, the fatty acid is metabolized the same as for saturated fatty acids. When oleic acid is P-oxidized, the first step (fatty acyl-GoA dehydrogenase) is skipped, and the isomerase deals with the cis double bond, putting it into the proper position and orientation to continue the pathway. 

El-Sharkawy, S.H., W. Yang, L. Dostal, and J.P.N. Rosazza, Microbial Oxidation of Oleic Acid, Appl. Environ. Microbiol 58 2116-2122 (1992). 

Guerrero, A., I. Casals, M. Busquets, Y. Leon, and A. Manresa, Oxidation of Oleic Acid to (E)-10-Hydroperoxy-8-octadecenoic and ( )-10-Hydroxy-8-octadecenoic Acids by Pseudomonas sp. 42A2, Biochim. Biophys. Acta 1347 75-81 (1997). 

Tsemg, K.-Y. Jin, SJ. (1991) J. Biol Chem., 266, 11614-11620, NADPH-dependent reductive metabolism of cis-5 unsaturated fatty acids. A revised pathway for the beta-oxidation of oleic acid. 

Azelaic acid can be prepared by the oxidation of oleic acid. Sebacic acid can be produced from castor oil. Brassylic acid can be synthesized from erucic acid via an ozonolysis reaction and with the aid of microorganisms from tridecane (55,56). The preparation of brassylic acid from tridecane occurs as follows (56) ... 

Palmitoleic (13) and similar acids may arise by p-oxidation of oleic acid (3). 

Voss LF, Bazerbashi MF, Beekman CP, Hadad CM, AUen HC (2007) Oxidation of oleic acid at airriiquid interfaces. J Geophys Res Atmos 112 D06209. doi 10.1029 006JD007677... 

King MD, Rennie AR, Thompson KC, Fisher FN, Dong CC, Thomas RK, Pffang C, Hughes AV (2009) Oxidation of oleic acid at the air-water interface and its potential effects on cloud critical supersaturations. Phys Chem Chem Phys 11 7699-7707... 

Schwier AN, Sateen N, Lathem T, Nenes A, McNeill VF (2011) Ozone oxidation of oleic acid films decreases aerosol CCN activity. J Geophys Res Atmos 116. doi 10.1029/ 2010JD015520... 

Microbial oxidation of oleic acid yields an epoxide. Write the structure of the product. 

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