10338-34-8

Basic information

• Product Name: (3beta,5beta,6beta)-3-hydroxy-5,6-epoxyandrostan-17-one
• Synonyms: (3beta,5beta,6beta)-3-Hydroxy-5,6-epoxyandrostan-17-one; (3beta,5beta,6beta)-5,6-Epoxy-3-hydroxyandrostan-17-one; androstan-17-one, 5,6-epoxy-3-hydroxy-, (3beta,5beta,6beta)-
• CAS NO: 10338-34-8
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.4238
• Mol File: 10338-34-8.mol

Chemical Properties

• Boiling Point: 451°C at 760 mmHg
• Flash Point: 160.1°C
• Density: 1.2g/cm³
• Vapor Pressure: 4.96E-10mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: (3beta,5beta,6beta)-3-hydroxy-5,6-epoxyandrostan-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,5beta,6beta)-3-hydroxy-5,6-epoxyandrostan-17-one(10338-34-8)
• EPA Substance Registry System: (3beta,5beta,6beta)-3-hydroxy-5,6-epoxyandrostan-17-one(10338-34-8)

Safety Data

• Hazardous Substances Data: 10338-34-8(Hazardous Substances Data)

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 108-05-4 vinyl acetate 

Relevant articles and documents

Microbiological hydroxylation of some epoxy steroids by the fungus Mucor plumbeus

The preparation of epoxy steroids derived from testosterone, dehydroisoandrosterone and epiandrosterone using m-chloroperbenzoic acid and their biotransformation by the fungus Mucor plumbeus is described. The results reveal an effect of the epoxide on the biotransformation.

Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate

Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations of steroids are reported. Among them, highly stereoselective epoxidation of Δ5-B-nor-cholestanes was achieved. Moreover, the method is chemoselective for the 5,6-position and can be applied to the epoxidation of ring-A enones.

Chemoselective epoxidation of cholesterol derivatives on a surface-designed molecularly imprinted Ru-porphyrin catalyst

A new molecularly imprinted Ru-porphyrin complex catalyst on a SiO2 support was designed, prepared, and characterized in a step-by-step manner for the C5C6 epoxidation of cholesterol derivatives. High chemoselectivity for the C5C6 epoxidation of cholesterol derivatives without protecting the 3-position OH group and other oxidizable functional groups was achieved on the molecularly imprinted catalyst.

The Preparation and Dienone-Phenol Rearrangement of Androsta-2,5-diene-4,17-dione

The preparation of androsta-2,5-diene-4,17-dione from dehydroisoandrosterone is described.Its dienone-phenol rearrangement, in the presence of hydrobromic acid and glacial acetic acid, affords 1-methyl-4-hydroxy-estra-1,3,5(10)-trien-17-one.

Poly(per)fluoroalkanesulfonyl fluoride promoted olefin epoxidation with 30% aqueous hydrogen peroxide

Epoxidation of various electron rich olefins with a novel oxidation system of poly(per)fluoroalkanesulfonyl fluoride/hydrogen peroxide/base is reported.

AMINO DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS

Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+, K+-ATPase. Said compounds are used for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

AMINO DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS

Compounds of formula (I) wherein:the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+,K+-ATPase. Said compounds are used for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

AZAHETEROCYCLYL DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS

Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+,K+-ATPase. They are useful for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.

Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol

Dehydroepiandrosterone (DHEA) reacted with m-chloroperoxybenzoic acid (m-CPBA) to form 3β-hydroxy-5α,6α-epoxyandrostan-17-one (1), but it did not react with 30 percent H2O2. 1,4,6-Androstatrien-3,17-dione (2) was obtained from DHEA and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. Compound 2 was reacted with 30 percent H2O2 and 5 percent NaOH in methanol to give 1α,2α-epoxy-4,6-androstadien-3,17-dione (3), which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-androstadien-3β,17β-diol (7) and reacted with Li metal in absolute ethanol-tetrahydrofuran mixture to give 2-ethoxy-1,4,6-androstatrien-3,17-dione (8). Compound 2 was also epoxidized with m-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4- androstadien-3,17-dione (4), which was reacted with NaBH4 to synthesize 6α,7α-epoxy-4-androsten-3β,17β-diol (9). Compound 4 was reduced with Li metal in absolute ethanol-tetrahydrofuran mixture to form 7β-ethoxy-6α-hydroxy-1,4-androstadien-3,17-dione (10). Compound 2 was reduced with NaBH4 in absolute ethanol to form 4,6-androstadien-3β,17β-diol (5), which was reacted with 30 percent H2O2 to give the original compound, but which reacted with m-CPBA to give 4β,5β-epoxy-6-androsten-3β,17β-diol (6).

Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids

Stereoisomerically pure 3β-hydroxy-5,6-epoxysteroids were obtained by combining selective chemical methods for α- and β-epoxidation of Δ5-unsaturated steroids with enzymatic stereoselective esterification of the 3β-hydroxyl group. 5β,6β-Epoxy-3β- hydroxysteroids were efficiently acylated by Novozym 435 and lipase AK, whereas 5α,6α-epoxy-3β-hydroxysteroids were good substrates for Candida rugosa lipase. Mild enzymatic deacylation of the 3β-acetoxy group in the presence of the epoxy functionality was also accomplished by C. rugosa lipase-mediated hydrolysis.