984-84-9

Basic information

• Product Name: cholest-4-en-3,6-dione
• Synonyms: cholest-4-en-3,6-dione;(20R)-Cholest-4-ene-3,6-dione;Cholest-4-ene-3,6-dione
• CAS NO: 984-84-9
• Molecular Formula: C₂₇H₄₂O₂
• Molecular Weight: 398.62
• Mol File: 984-84-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 503.4°Cat760mmHg
• Flash Point: 186.1°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 2.92E-10mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: cholest-4-en-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: cholest-4-en-3,6-dione(984-84-9)
• EPA Substance Registry System: cholest-4-en-3,6-dione(984-84-9)

Safety Data

• Hazardous Substances Data: 984-84-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H42O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h15,17-18,20-23H,6-14,16H2,1-5H3/t18-,20+,21-,22+,23+,26-,27-/m1/s1

Upstream product

• 57-88-5 cholesterol 
• 601-54-7 Cholest-5-en-3-one 
• 601-57-0 Cholest-4-en-3-one 
• 1250-95-9 5α,6α-epoxycholestan-3β-ol 
• 110-86-1 pyridine 
• 1857-80-3 5α,6β-dibromocholestan-3β-ol 
• 17320-10-4 4β-hydroxycholesterol 
• 16732-86-8 cholest-4-ene 
• 601-54-7 Δ⁵-cholesten-3-one 
• 2207-76-3 6β-Hydroperoxycholest-4-en-3-one 

Downstream Products

• 469-04-5 acide de Butenandt 
• 911477-51-5 cholestatriene-(3.5.7)-diyl-(3.6)-dibenzoate 
• 570-91-2 3β-hydroxycholest-4-en-6-one 
• 570-90-1 6α-hydroxy-cholest-4-en-3-one 
• 2243-09-6 (5S,8S,9S,10R,13R,14S,17S)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,6-dione 
• 103216-19-9 3-oxo-2'-phenyl-4-cholesteno<4,6-cd>pyrazole 
• 481-21-0 cholestane 
• 103216-20-2 2'-phenyl-4-cholesteno<4,6-cd>pyrazol-3-one phenylhydrazone 
• 17608-41-2 cholestanol 
• 481-20-9 cholestane 
• 1409976-56-2 3-(4-methoxyphenylimino)cholest-4-en-6-one 
• 1409976-60-8 3-(4-methoxyphenylimino)cholest-4-en-6-one 
• 1450594-00-9 C₃₃H₄₇N₃O₃ 
• 1450594-02-1 C₃₃H₄₄F₄N₂O 

Relevant articles and documents

Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption

7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature of this synthesis involves a regioselective C3-allylic oxidation of a 3-desoxy-Δ4-7α-formate steroid precursor to form 7α-formyloxy-cholest-4-en-3-one, which was saponified to yield 7α-hydroxy-cholest-4-en-3-one.

Oxysterols: Synthesis and anti-leishmanial activities

Oxygenated sterols (2-16) were synthesized by skeletal rearrangement of steroidal allylic alcohols. All the derivatives were screened for their anti-leishmanial activities. Compounds 3, 11 and 12 showed potent activities. Compound 12 was found least toxic and induced highest nitric oxide (NO) at 48 h. Least toxicity of compound 12 on splenocytes validated its best anti-amastigote effect and induction of NO.

Stereospecific oxidation of 3β-hydroxysteroids by persolvent fermentation with Pseudomonas sp. ST-200

Pseudomonas sp. strain ST-200 isolated from a humus soil effectively oxidizes cholesterol dissolved in organic solvents but not that suspended in the growth medium. The organism does not assimilate cholesterol. This organism oxidized a variety of 5α- or 5-ene-steroids dissolved in organic solvent. First, the 3β-OH group was oxidized to a ketone group. The 3α-OH group was scarcely oxidized. Successively, C-6 position of 5-ene-steroids was hydroxylated, and a double bond of 5-ene-steroids was transferred from Δ5 to Δ4. Then, the 6-OH group was oxidized to a ketone group. Persolvent fermentation with ST-200 would provide an effective, convenient, and stereospecific method to oxidize the C-3 and C-6 positions of steroids.