18472-36-1

Basic information

• Product Name: DELTA5-AVENASTEROL
• Synonyms: DELTA5-AVENASTEROL;24-Ethylidenecholest-5-en-3β-ol;24-Ethylidenecholesterol;5-Avenasterol;Sargasterol;Stigmasta-5,24(28)-dien-3β-ol;Δ5-Avenasterol;24-Ethylcholesta-5,24(28)-dien-3beta-ol
• CAS NO: 18472-36-1
• Molecular Formula: C₂₉H₄₈O
• Molecular Weight: 412.69082
• Mol File: 18472-36-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 504.2°Cat760mmHg
• Flash Point: 220.3°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 2.8E-12mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 15.03±0.70(Predicted)
• CAS DataBase Reference: DELTA5-AVENASTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: DELTA5-AVENASTEROL(18472-36-1)
• EPA Substance Registry System: DELTA5-AVENASTEROL(18472-36-1)

Safety Data

• Hazardous Substances Data: 18472-36-1(Hazardous Substances Data)

Usage

Uses

Δ5-Avenasterol is an analog of Stigmasterol (S686750); a plant sterol that is used as a precursor in the synthesis of progesterone.

InChI:InChI=1/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3

Upstream product

• 108864-88-6 3β-acetoxy-20β_FH,24ξH-stigmast-5-en-24-ol 
• 84413-10-5 Acetic acid (3S,8S,9S,10R,13R,14S,17R)-17-((S)-4-hydroxy-4-isopropyl-1-methyl-hex-5-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 83946-09-2 (20S,22E)-24-Oxo-5,22-cholestadien-3β-yl-acetat 
• 84253-70-3 saringosterol 
• 15626-16-1 (20R)-22-Oxo-23,24-dinor-5-cholen-3β-yl-acetat 
• 61277-82-5 17β-<(2R)-2-Methyl-2-oxiranyl>-5-androsten-3β-yl-acetat 
• 83946-10-5 (20S)-24-Oxo-5-cholesten-3β-yl-acetat 
• 83946-11-6 (20S)-3β-Hydroxy-5-cholesten-24-on 
• 19753-67-4 3-methyl-1-(triphenylphosphoranyliden)-2-butanone 
• 17752-16-8 24-oxocholesterol 
• 474-63-5 24-methylene cholesterol 
• 14031-35-7 S-Adenosyl-L-methionine 
• 51297-12-2 fucosterol acetate 
• 120328-68-9 3β-acetoxy-24ξH-stigmast-5-en-24-ol 

Downstream Products

• 6035-63-8 3β-benzoyloxy-stigmasta-5,24(28)t-diene 
• 83-45-4 Stigmastanol 
• 6160-48-1 3.5-dinitro-benzoic acid-(5α-stigmastanyl-(3β)-ester) 
• 107493-31-2 (24R)-5α-stigmastan-3β-ol benzoate 
• 4736-94-1 stigmastan-3-one 
• 75-07-0 acetaldehyde 
• 6035-62-7 (10R)-3c-Acetoxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4t)-yl)-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren 
• 51297-12-2 fucosterol acetate 
• 85081-01-2 fucosterol tetra-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Stereochemical fate of C-26 and C-27 during the conversion of isofucosterol to sitosterol and of 24-methylenecholesterol to campesterol and dihydrobrassicasterol in Oryza sativa cell cultures

Administration of pro-R-methyl-13C-labeled isofucosterol to cultured cells of Oryza sativa revealed that the pro-R and pro-S methyls at C-25 become the pro-R and pro-S methyls at C-25 of sitosterol, respectively. Similar administration experime

Partial Synthesis of "Sargasterol" and (20S)-Cholesterol

The data of the synthetic (20S)-3β-hydroxy-5-cholestan-24-one (5b) and its acetate 5a differ significantly from those given for the degradation product of "sargasterol".The compounds 5a,b were converted into the E/Z-isomeric (20S)-stigmasta-5,24(28)-dien-3β-ols 8b, 9b, into their acetates 8a, 9a, and into (20S)-cholesterol (10b). (20S)-cholesterol acetate (10a) shows a lower melting point than that which is given in literature.