Dihydrocholesterol

DescriptionDihydrocholesterol (cholestanol; 5α-cholestan-3β-ol) is a cholesterol metabolite formed by oxidation and an intermediate in the biosynthesis of chenodeoxycholic acid . Cholestanol (10 μg/ml) induces apoptosis in cornea and lens epithelial cells and increases the activity of IL-1β converting enzyme (ICE) and CPP32 proteases. Dietary administration of 1% cholestanol to mice increases serum and liver cholestanol levels and leads to corneal opacities and gallstones and in rats it leads to cholestanol deposition in the cerebellum. Cholestanol levels are increased in plasma of patients with cerebrotendinous xanthomatosis (CTX), a disease characterized by a deficiency in the mitochondrial enzyme sterol 27-hydrolylase (CYP27A1) that leads to progressive neurological symptoms.

Uses5α-Cholestan-3β-ol is a carbon stanol formed from biohydrogenation of Cholesterol (C432501) in the gut. Studies have also examined the conversion of 5α-Cholestan-3β-ol catalyzed by 3-β-hydroxysteroid dehydrogenase of rat liver.

Uses5alpha-Cholestan-3beta-ol is used as a standard in lipid analysis using HPLC. It acts as a derivitized steroid compound. It is used in agrochemical, pharmaceutical and dyestuff field .

General DescriptionCholestanol is a 5α-dihydro derivative of cholesterol. It acts as a marker for cholesterol absorption. Cholestanol is a steroid with 27 carbon atoms.

PreparationDihydrocholesterol can be prepared either by chemical synthesis or by extraction from natural sources. Chemical synthesis typically uses cholesterol as the starting material. Hydrogenation is carried out in a solvent such as glacial acetic acid using a catalyst, for example platinum oxide, to reduce the C5–C6 double bond, followed by purification through saponification and crystallisation. Alternatively, dihydrocholesterol may be isolated from natural materials, including animal tissues such as bovine brain and liver, or purified from gallstones.