114882-48-3

Basic information

• Product Name: trichechol
• Synonyms: trichechol
• CAS NO: 114882-48-3
• Molecular Formula: C27H48O5
• Molecular Weight: 452.66702
• Mol File: 114882-48-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 598.4°Cat760mmHg
• Flash Point: 252°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 8.17E-17mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: trichechol(CAS DataBase Reference)
• NIST Chemistry Reference: trichechol(114882-48-3)
• EPA Substance Registry System: trichechol(114882-48-3)

Safety Data

• Hazardous Substances Data: 114882-48-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H48O5/c1-16(6-5-11-25(2,32)15-28)18-7-8-19-22-20(10-13-26(18,19)3)27(4)12-9-17(29)14-21(27)23(30)24(22)31/h16-24,28-32H,5-15H2,1-4H3/t16-,17-,18-,19+,20+,21+,22+,23+,24+,25?,26-,27-/m1/s1

Upstream product

• 3664-87-7 3α-hydroxy-5β-chol-6-en-24-oic acid 
• 61289-17-6 methyl 3α-acetoxy-5β-chol-6-en-24-oate 
• 125380-60-1 Acetic acid (3R,5R,6S,7S,8S,9S,10R,13R,14S,17R)-3,7-diacetoxy-17-((R)-6-diazo-1-methyl-5-oxo-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 
• 125380-56-5 (R)-5-((3R,5R,6S,7S,8S,9S,10R,13R,14S,17R)-3,6,7-Triacetoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-hexanoic acid 
• 125380-57-6 Acetic acid (3R,5R,6S,7S,8S,9S,10R,13R,14S,17R)-3,7-diacetoxy-17-((R)-4-chlorocarbonyl-1-methyl-butyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yl ester 
• 125380-54-3 α-formoxy-25-diazo-26,27-dinor-5β-cholestan-24-one 
• 125380-59-8 methyl 3α,6β,7α-trihydroxy-26,27-dinor-5β-cholestan-25-oate 
• 125380-52-1 (R)-4-((3R,5S,8S,9S,10S,13R,14S,17R)-3-Formyloxy-10,13-dimethyl-2,3,4,5,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 
• 125380-53-2 Formic acid (3R,5S,8S,9S,10S,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-10,13-dimethyl-2,3,4,5,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 125380-55-4 (R)-5-((3R,5S,8S,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,5,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-hexanoic acid methyl ester 
• 125380-50-9 3α,6β,7α-trihydroxy-26,27-dinor-5β-cholestan-25-oic acid 
• 125380-49-6 3α-hydroxy-26,27-dinor-5β-cholest-6-en-25-oic acid 
• 917-64-6 methyl magnesium iodide 
• 125380-51-0 3α,6β,7α,26-tetraacetoxy-27-nor-5β-cholestan-25-one 

Relevant articles and documents

Synthesis of 5 beta-cholestane-3 alpha,6 beta,7 alpha,25,26-pentol and identification of a novel bile alcohol, alpha-trichechol, present in the West Indian manatee bile.

In order to confirm the structure of alpha-trichechol, the major bile alcohol of the West Indian manatee, chemical synthesis of 5 beta-cholestane-3 alpha,6 beta,7 alpha,25,26-pentol was carried out. The chain of 3 alpha-hydroxy-5 beta-chol-6-en-24-oic acid was elongated by an Arndt-Eistert reaction to form 3 alpha-hydroxy-26,27-dinor-5 beta-cholest-6-en-25-oic acid. The unsaturated C25 bile acid was converted into 3 alpha,6 beta,7 alpha-trihydroxy-25-homo-5 beta-cholan-25-oic acid by 1,2-glycol formation of the delta 6-double bond. The acetylated derivative of the trihydroxy C25 bile acid was then converted into 3 alpha,6 beta,7 alpha,26-tetraacetoxy-27-nor-5 beta-cholestan-25-one by successive treatment with thionyl chloride, diazomethane, and acetic acid. A Grignard reaction of the 25-oxo compound with methylmagnesium iodide afforded the desired bile alcohol, 5 beta-cholestane-3 alpha,6 beta,7 alpha,25,26-pentol. By direct comparison with the synthetic pentahydroxy bile alcohol, the structure of the naturally occurring alpha-trichechol was determined to be 5 beta-cholestane-3 alpha,6 beta,7 alpha,25,26-pentol.