Sterol metabolism. XLIII. The oxidation of cholest-4-en-3β-ol by singlet molecular oxygen
✍ Scribed by Jon I. Teng; Chow-Eng Low; Leland L. Smith
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- English
- Weight
- 498 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
The photosemitized oxidation of cholest-4-en-3#-ol in which singlet molecular oxygen is implicated yielded eholut4-en-3-one and the isomeric epoxides 4~,5-epoxy-5~-cholestan-3-one and 4#,5-epoxy-50-cholestan-3-one, the epoxides being formed in the ratio 3 : 1. Oxidation of cholest4~n-3-one by alkaline hydrogen peroxide likewise yielded the isomeric 4~%epoxides but in the ratio 1 : 7.4. Attempted use of cholest-4-en-3&ol to intercept singlet molecular oxygen putatively generated in the disproportionation of hydrogen peroxide gave a very complex product mixture of over 50 components from which only cholestAcn-3-one could be identified. However, neither isomeric 4,5-epoxycholestan-3 one was detected among the products. These data establish that it is unwaxranted to infer the action of single molecular oxygen in systems containing cholest-4-en-3#-ol merely by product analysis where the product 4~5-epoxy-Sa-cholestan-3~)ne is formed.