Octadecanol, oxidation

Octadecanol oxidizes with the formation of acids, esters and carbonyl compounds [16]. Stearic acid predominates among the acids thus indicating primary oxidation of the alcohol group. 

This approach, shown in Figure 4, [36] has been followed to prepare numerous deuterated stearic acids. Actually, the a,a -deuterated hydroxystearate is often transformed into the -toluenesulfonyl derivative that, in turn, was treated with lithium aluminum hydride to obtain the deuterated octadecanol. Oxidation of this latter give deuterated stearic acid. If hthium aluminum deuteride is used instead of LiAlH4, nucleophilic substitution of the tosylate with deuterium can be accomplished. 

Fatty alcohohNAD oxidoreductase is a complex enzyme which consists of two separate proteins that sequentially catalyze the oxidation of fatty alcohol to fatty aldehyde and to fatty acid that is to say a fatty alcohol dehydrogenase and a fatty aldehyde dehydrogenase (FALDH) activity. Sjogren-Larsson cells were selectively deficient in the FALDH component and had normal activity of fatty alcohol dehydrogenase. Intact fibroblast oxidized octadecanol to fatty acid at <10% of the normal rate but oxidized octadecanal normally confirming that FALDH is specifically affected (Rizzo and Craft, 1991). 

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