28893-44-9

Basic information

• Product Name: 1alpha,2alpha-epoxycholesta-4,6-dien-3-one
• Synonyms: 1alpha,2alpha-epoxycholesta-4,6-dien-3-one;1α,2α-Epoxy-4,6-cholestadien-3-one;1α,2α-Epoxycholesta-4,6-dien-3-one
• CAS NO: 28893-44-9
• Molecular Formula: C₂₇H₄₀O₂
• Molecular Weight: 396.6053
• EINECS: 249-291-8
• Mol File: 28893-44-9.mol

Chemical Properties

• Boiling Point: 514°Cat760mmHg
• Flash Point: 191.9°C
• Appearance: /
• Density: 1.06g/cm³
• CAS DataBase Reference: 1alpha,2alpha-epoxycholesta-4,6-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1alpha,2alpha-epoxycholesta-4,6-dien-3-one(28893-44-9)
• EPA Substance Registry System: 1alpha,2alpha-epoxycholesta-4,6-dien-3-one(28893-44-9)

Safety Data

• Hazardous Substances Data: 28893-44-9(Hazardous Substances Data)

Usage

Structure

Cholesterol-like structure with an epoxide functional group

Source

Natural product derived from various plant and animal sources

Biological Activities

a. Anti-inflammatory
b. Antiproliferative
c. Antioxidant

Potential Applications

a. Treatment of cardiovascular diseases
b. Treatment of cancer
c. Treatment of neurodegenerative disorders

Investigation for Bioactivity

Studied as a potential bioactive compound in functional foods and dietary supplements

Upstream product

• 3464-60-6 cholesta-1,4,6-trien-3-one 
• 106239-97-8 1α,2α-epoxycholesta-4,6-diene-3α-ol 
• 57-88-5 cholesterol 
• 566-93-8 cholesta-4,6-dien-3-one 
• 75981-10-1 cholesta-1,4,6-trien-3-one p-nitrophenylhydrazone 

Downstream Products

• 26358-75-8 1α,3β-dihydroxycholest-5-ene 
• 35339-68-5 (5-Cholesten-1α,3β-diol)-diacetat 
• 3464-60-6 cholesta-1,4,6-trien-3-one 

Relevant articles and documents

Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents

Taking into account the structural requirements for cytotoxicity, several new hydroximinosteroid derivatives have been prepared and evaluated for their cytotoxic activity against A-549, H116, PSN1, and T98G cultured tumor cell lines in order to obtain further information on the potential pharmacophoric core of this type of compound. The influence of the oxygenated position in the A ring, the presence of an additional oxygenated position at C-7 and C-16, and a fluorinated position at C-5 were considered in order to study the structure-activity relationships. The results reveal the importance of oxygenated positions in the A ring (e.g., 4,5-epoxide showed an IC50 value against HCT-116 under micromolar level) for an increase in cytotoxic activity in this type of compound. Furthermore, they showed an important selectivity toward colon tumor line (HCT-116).

Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3β-ol

Many naturally occurring polyhydroxylated sterols and oxysterols exhibit potent biologic activities. This paper describes reagent and position selectivity of epoxidation and reduction of cholesterol derivatives. Cholesterol was reacted with m-chloroperoxybenzoic acid (m-CPBA) to form 5α,6α-epoxycholestan-3β-ol, but in reaction with 30% H 2O2, it did not reacted. 1,4,6-Cholestatrien-3-one was obtained from cholesterol and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. 1,4,6-Cholestatrien-3-one was reacted with 30% H2O 2 and 5% NaOH in methanol to give 1α,2α-epoxy-4,6- cholestadien-3-one, which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-cholestadien-3β-ol and reduced with Li metal in absolute ethanol to give 2-ethoxy-1,4,6-cholestatrien-3-one. And 1,4,6-cholestatrien-3-one was epoxidized with m-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4-cholestadien-3-one, which was reacted with NaBH4 to synthesize 6α-hydroxy-4-cholesten-3-one and reduced Li metal in absolute ethanol to form 2-ethoxy-1,4,6-cholestatrien-3-one, respectively. 1,4,6-Cholestatrien-3-one was reduced with NaBH4 in absolute ethanol to form 4,6-cholestadien-3β-ol, which was reacted with 30% H2O2 to leave original compound, but was reacted with m-CPBA to give 4β,5β-epoxy-6-cholesten-3β-ol as the major product and 4β,5β-epoxy-6α,7α-epoxycholestan-3β-ol as the minor product.

1-α-hydroxy vitamin D compounds and process for preparing same

The invention provides novel 1α-hydroxy vitamin D compounds and a method for their preparation from 1α-hydroxy-25-hydrogen cholesta-5,7-dienes by irradiation and isomerization techniques. The invention also includes the said 1α-hydroxy-25-hydrogen-cholesta-5,7-dienes and the corresponding cholest-5-enes. The new compounds may be obtained in a crystalline form substantially free from isomeric or other impurities arising from manufacture.

Steroidal Allylic Epoxides

Two allylic epoxides, 4β,5β-epoxycholest-6-en-3β-ol and 4α,5α-epoxycholest-6-ene-1α,3α-diol, were obtained by reaction of the corresponding conjugated dienols with t-butyl hydroperoxide in the presence of bisacetylacetonato-oxovanadium as catalyst.The reductive opening of these epoxides and other related reactions are discussed.

Dehydrogenation of Steroidal and Triterpenoid Ketones using Benzeneseleninic Anhydride

Steroid and triterpenoid ketones can by smoothly dehydrogenated in high yield with benzeneseleninic anhydride in chlorobenzene at 95-120 deg C.With the excess of benzeneseleninic anhydride and longer reaction times 4,4-dimethyl ketones give ring-A-contracted diketones in moderate yields.

Oxidation of Ketone and Aldehyde Hydrazones, Oximes, and Semicarbazones and of Hydroxylamines and Hydrazo-compounds, using Benzeneselenic Anhydride

Benzeneseleninic anhydride (1; BSA) is an effective reagent for the mild regeneration of the carbonyl group from ketone phenylhydrazones, p-nitrophenylhydrazones, tosylhydrazones, oximes, and semicarbazones at 40-50 deg C.Tosylhydrazones and oximes of aldehydes are also readily converted into the parent aldehyde.The phenylhydrazone and p-nitrophenylhydrazone derivatives of aldehydes afford ketoazo-compounds.The ketoazo-species could also be prepared by oxidation of the corresponding hydrazide with compound (1).Both aromatic and aliphatic hydrazo-compounds and hydroxylamines can be oxidised to azo- and nitrozo-derivatives respectively.