3404-22-6

Usage

InChI:InChI=1/C26H42O/c1-17(2)6-5-7-18(3)24-12-13-25-23-10-8-19-16-20(27)9-11-21(19)22(23)14-15-26(24,25)4/h16-18,21-25H,5-15H2,1-4H3/t18-,21+,22-,23-,24-,25+,26-/m1/s1

Upstream product

• 14413-31-1 3β-acetoxycholest-5-en-19-oic acid 
• 3111-05-5 6-oxo-3α,5-cyclo-5α-cholestan-19-oic acid 
• 14413-32-2 19-norcholest-5(10)-en-3β-yl acetate 
• 137436-18-1 (25ξ)-26-hydroxy-19-norcholest-5(10)-en-3-one 3-(ethylene thioketal) 
• 137435-87-1 (25ξ)-26-<(tert-butyldiphenylsilyl)oxy>-19-norcholest-5(10)-en-3-one 
• 137435-78-0 tert-Butyl-[(R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methyl-heptyloxy]-diphenyl-silane 
• 137435-90-6 C₃₅H₅₂O₃S₃ 
• 137435-89-3 (25ξ)-19-norcholest-5(10)-ene-3,26-dione 3-(ethylene thioketal) 
• 137435-75-7 ethyl (25ξ)-6β-methoxy-3α,5-cyclo-5α-cholestan-26-oate 
• 57984-04-0 6β-methoxy-3α,5-cyclo-5α-chol-23-en-22-ol 
• 137435-76-8 (R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methyl-heptan-1-ol 
• 106337-92-2 19-norcholest-5⁽¹⁰⁾-en-3-one 
• 55538-94-8 19-Norcholest-5(10)-en-3β-ol 
• 2137-16-8 19-norcholest-5-en-3β-ol 

Relevant academic research and scientific papers

OCCURRENCE AND SEASONAL VARIATION OF 19-NORCHOLEST-4-EN-3-ONE AND 3β-MONOHYDROXY STEROLS IN THE CALIFORNIAN GORGONIAN, MURICEA CALIFORNICA

The first natural occurrence of 19-norcholestenone is reported, together with 17 sterols and one other Δ4-3-ketone in the extracts of the Californian gorgonian, Muricea californica (Aurivillius).Six additional demethyl sterols and five additional 4-monomethyl sterols which remain unidentified were also detected.Lipid extracts of M. californica from a winter and summer collection were split by various chromatographic methods into free sterol, steryl ester, and steryl conjugate fractions.Sterol compositions (determined by GC and GC-MS) of each fraction, subsequent to hydrolysis, are tabulated and discussed with respect to plausible origins of observed variations.The possible relationship of the Muricea 19-nor-steroidal ketone to other naturally occurring 19-nor-steroids is discussed.

Biosynthetic studies of marine lipids. 39.1 19-norsterols: The course of c-19 methyl elimination

The biosynthesis of 19-norstanols in the Mediterranean sponge, Axinella polypoides, was investigated through the use of radiotracer experiments. It was found that the conversion of cholesterol (7) to 19-nor-5α-chotestan-3β-ol (8) involved oxidation at C-3 with the distribution of the abstracted hydride from the 3α-position of dietary cholesterol into all of the 19-norstanols of the native mixture. Furthermore, while the efficiency of conversion of Δ5-19-oxygenated sterol precursors 19-hydroxycholesterol (9) and 3β-hydroxycholest-5-en-19-oic acid (10) to 8 was low, the efficiency of the conversion of 19-hydroxycholest-4-en-3-one (23) to 8 was high, suggesting that the principal pathway for 19-norstanol biosynthesis involves oxidative isomerization of a dietary Δ5-3β-hydroxy sterol to the δ4-3-ketone before oxidation at C-19. It was also shown that the conversion of cholesterol to 19-nor-5α-cholestan-3β-ol involves the stereospecific loss of the 4β-hydrogen atom. It was further determined that the biological demethylation pathway is suppressed for dietary sterols bearing an unconventional configuration at C-20 in the hydrocarbon side chain.

Photoinduced Molecular Transformations. Part 112.Transformation of Steroids into Ring-A-Aromatized Steroids and 19-Norsteroids involving a Regioselective β-Scission of Alkoxyl Radicals; Synthesis of Two Marine Natural Products, 19-Nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one...

A new transformation of steroids into 19-norsteroids and ring-A-aromatized steroids is described.The transformation method involves the removal of the 10β-methyl group by a regioselective β-scission of alkoxyl radicals.Cholesterol was transformed into two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and into 19-norcholesta-1,3,5(10)-trien-3-ol.Transformations of 3β-hydroxyandrost-5-en-17-one into 19-nortestosterone, estrone, and the related estranes are also described.