521-10-8

Basic information

• Product Name: Methandriol
• Synonyms: 17-alpha-Methyl-5-androstene-3-beta,17-beta-diol;17alpha-Methylandrost-5-ene-3beta,17beta-diol;17alpha-Methyl-delta5-androsten-3beta,17beta-diol;17-beta-diol,17-methyl-androst-5-ene-3-bet;17-Methylandrost-5-ene-3,17-diol;17-methylandrost-5-ene-3-beta,17-beta-diol;Androdiol;Androst-5-ene-3,17-diol, 17-methyl-,
• CAS NO: 521-10-8
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.47
• EINECS: 208-301-0
• Product Categories: Steroids;Biochemistry;Hydroxysteroids
• Mol File: 521-10-8.mol

Chemical Properties

• Melting Point: 205 °C
• Boiling Point: 385.28°C (rough estimate)
• Flash Point: 192.3°C
• Appearance: /
• Density: 1.0279 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -75 ° (C=1, EtOH)
• PKA: 15.01±0.70(Predicted)
• Merck: 5950
• CAS DataBase Reference: Methandriol(CAS DataBase Reference)
• NIST Chemistry Reference: Methandriol(521-10-8)
• EPA Substance Registry System: Methandriol(521-10-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 16-23-36
• RIDADR: 3249
• RTECS: BV8100000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 521-10-8(Hazardous Substances Data)

Usage

Uses

A metabolite of 17α-Methyltestosterone (M326400).

Brand name

Methostan (Schering) .

Safety Profile

Human reproductive effects by anunspecified route: developmental abnormalities of theurogenital system. A human and experimental teratogen.When heated to decomposition it emits acrid smoke andirritating fumes.

InChI:InChI=1/C20H32O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h4,14-17,21-22H,5-12H2,1-3H3/t14-,15-,16-,17+,18-,19-,20-/m0/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 53-43-0 dehydroepiandrosterone 
• 34988-21-1 3β,17-diacetoxy-21-nor-17βH-pregnen-(5)-oic acid-(20)-nitrile 
• 100-66-3 methoxybenzene 
• 853-23-6 prasterone acetate 
• 917-54-4 methyllithium 
• 570-78-5 3α,6α-dihydroxy-5β-pregnan-20-one 
• 1474-72-2 3α,6α-dihydroxy-5β-androstan-17-one 
• 69841-33-4 17α-Methyl-5β-androstantriol-(3α,6α,17β) 
• 74-87-3 methylene chloride 

Downstream Products

• 641-82-7 ZIN⁽²²³⁾C₀₅₄₅₁ 
• 58-18-4 17-methyltestosterone 
• 846-44-6 3β-hydroxy-10.13-dimethyl-17-methylene-gonene-(5) 
• 3593-85-9 methandriol dipropionate 
• 846-45-7 17-Methylene-4-androstene-3-one 
• 846-43-5 3β-hydroxy-10.13.17-trimethyl-gonadiene-(5.16) 
• 92010-66-7 methylandrostenediol di-p-fluorobenzoate 
• 105546-95-0 17α-Methyl-3β-sulfooxyandrost-5-en-17β-ol triethylammonium salt 
• 116030-95-6 17-methyl-3β-(3-phenyl-propionyloxy)-androst-5-en-17β-ol 
• 40129-19-9 17-methyl-3β-(toluene-4-sulfonyloxy)-androst-5-en-17β-ol 
• 2061-86-1 3β.17β-diacetoxy-17α-methyl-androstene-(5) 
• 117273-51-5 phthalic acid mono-(17β-hydroxy-17α-methyl-androst-5-en-3β-yl ester) 

Relevant articles and documents

A New Deprotection Procedure of MTM Ether

A new deprotection procedure of methylthiomethyl (MTM) ether, a protective group for the hydroxy group, was developed. MTM was oxidized with MCPBA or Oxone, and the resulting sulfoxide was treated under conditions of the Pummerer rearrangement, to give acetoxy sulfide and/or acetoxy acetal. Alkaline hydrolysis of the products provided the unprotected alcohols in good yields. Details of the reactions using several different substrates are described.

SYNTHESIS OF SOME EPITESTOSTERONE ANALOGUES

11β-Hydroxyandrost-4-ene-3,17-dione (III) was converted into a potential metabolite of epitestosterone - 11β,17α-dihydroxyandrost-4-en-3-one (II) in 5 steps, including the inversion of configuration of a 17β-hydroxy group.This inversion was not feasible in the preparation of the analogues X, XIV, XX, and XXII, where the 17α-hydroxy group was introduced first and only then was the rest of molecule modified.

Microbiological degradation of sterol side chains to a 17-keto group

The side chains of sterols are degraded by fermentation with microorganisms capable of doing so in an improved manner by employing in such fermentations sterol derivatives of the formula STR1 wherein n is 1 or 2; R1 is H or lower alkyl, R2 is alkyl, whose chain optionally is interrupted by an oxygen atom, or when n is 2, also a hydrogen atom; and R3 is a sterol side chain.