1256-31-1

Basic information

• Product Name: 5,6-β-epoxycholesteryl acetate
• Synonyms: 5,6-β-epoxycholesteryl acetate
• CAS NO: 1256-31-1
• Molecular Weight: 444.698
• Mol File: 1256-31-1.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 5,6-β-epoxycholesteryl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-β-epoxycholesteryl acetate(1256-31-1)
• EPA Substance Registry System: 5,6-β-epoxycholesteryl acetate(1256-31-1)

Safety Data

• Hazardous Substances Data: 1256-31-1(Hazardous Substances Data)

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 604-35-3 Cholesteryl acetate 
• 1258-07-7 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-13-methyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-6,10-(epoxymethano)cyclopenta[a]phenanthren-3-yl acetate 
• 112-79-8 Elaidic acid 
• 60-33-3 (9E,12E)-Octadeca-9,12-dienoic acid 
• 28290-79-1 trans-linolenic acid 
• 14050-40-9 oleic acid hydroperoxide 
• 7695-64-9 linoleic acid hydroperoxide 
• 19355-87-4 linolenic acid hydroperoxide 
• 108-05-4 vinyl acetate 
• 55700-78-2 (6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol 
• 1258-35-1 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-6-hydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 604-35-3 cholest-5-en-3β-yl acetate 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 111650-73-8 5,6β-epoxy-5β-cholest-3β-yl 3-oxobutyrate 
• 2953-38-0 5beta,6beta-Epoxycholestanol 
• 604-35-3 Cholesteryl acetate 
• 133586-85-3 3β-acetoxy-5α-cholestano<6a,5d>-1',3'-oxathiolane-2-thione 
• 106057-62-9 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-6-p-tolylsulfanyl-hexadecahydro-cyclopenta[a]phenanthrene-3,5-diol 
• 56376-32-0 6β-bromo-5α-cholestane-3β,5-diol 3-acetate 
• 2953-37-9 3β,5-dihydroxy-5α-cholestan-6-one 
• 6120-71-4 3β,5α-dihydroxycholestan-6β-yl acetate 
• 2515-01-7 5-α-hydroxy-cholestan-3-one 
• 2572-56-7 5β-methyl-19-norcholest-9(10)-ene-3β,6β-diol 3,6-diacetate 
• 6770-44-1 5α-hydroxy-3β-p-toluenesulfonyloxycholestan-6-one 
• 570-91-2 3β-hydroxycholest-4-en-6-one 
• 38404-75-0 cholestene-(5)-diyl-(3β.6)-dibenzoate 
• 119804-44-3 3β-acetoxy-5α-butanoyloxy-6β-(4-methylphenylthio)cholestane 

Relevant articles and documents

Synthetic study of strongylophorines: stereoselective construction of the characteristic lactone bridge

Herein, we report an efficient construction of the lactone bridge of strongylophorine-2, which is a meroditerpenoid isolated from Strongylophora durissima and an inhibitor for HIF-1 transcriptional pathway. Starting from dehydroepiandrosterone acetate, the characteristic lactone has been constructed in 5.4% over 18 steps by employing, (1) modified oxy radical-mediated C–H functionalization at the C24 methyl group, and (2) four-step manipulation of C4 quaternary carbon stereogenic center. The lactone synthesized here is expected as a precursor for (8-desmethyl)strongylophorine-2 which is of particular interest in terms of structure–activity relationships in the inhibition of HIF-1 transcriptional pathway.

A new electrochemical system for stereoselective allylic hydroxylation of cholesteryl acetate with dioxygen induced by iron picolinate complexes

The oxygenation reaction of cholesteryl acetate 1 was examined with the FeIII(PA)3/O2/MeCN system using an electrochemical method. The constant potential technique gave mainly the 7-hydroxylated product stereoselectively, along with the 7-oxo product. This oxygenation system is mechanistically unique, requiring iron catalyst, dioxygen, and both cathode and anode.

Iron(III)picolinate-catalyzed oxygenation of cholesteryl acetate with hydrogen peroxide or peracetic acid

The reaction of cholesteryl acetate 1 with a Fe(III)(PA; picolinate)3/H2O2/MeCN system (reagent system A), a simple model system for mono-oxygenases, gave mainly the 7α-hydroxylation product 2a, along with 7-ketonization product 3 and the 5,6-epoxidation product 4. On the other hand, reaction of 1 using a Fe(PA)3/peracetic acid (AcOOH)/MeCN system (reagent system c) or a Fe(III)(ClO4)3 · 9H2O-picolinic acid(PAH)- pyridine(Py)/AcOOH/MeCN system (reagent system F), provided 4 predominantly without formation of 2a. The former reaction may proceed via the dimeric Fe(III)-Fe(V) manifold complex, (PAH)(PA)2Fe(III)-O-O-Fe(V)=O(PA)2 (VII) as a hypothetically active species and a nonradical pathway, and the latter may proceed through monomeric iron complexes, [(PAH)(PA)2Fe(V)=O]+ (IX) and [(PAH)(PA)2Fe(V)(OH)(OOH)I+ (X).