3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid

Base Information

• Chemical Name: 3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
• CAS No.: 15173-54-3
• Molecular Formula: C20H32 O3
• Molecular Weight: 320.472
• NSC Number: 179301,224317
• DSSTox Substance ID: DTXSID20934338
• Mol file: 15173-54-3.mol

Synonyms:15173-54-3;3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid;(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid;3-Hydroxyandrostane-17-carboxylic acid;3-Hydroxyandrostane-17-carboxylic acid #;DTXSID20934338;KAYYIYDHRSEWHR-UHFFFAOYSA-N;HMS1787A02;3.beta.-Hydroxyetioallocholanic acid;NSC179301;NSC224317;AKOS001028535;NSC-179301;NSC-224317;FT-0774165;Z56758426;3-BETA-HYDROXY-5-ALPHA-ANDROSTANE-17-BETA-CARBOXYLICACID

Chemical Property of 3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.39E-10mmHg at 25°C
• Melting Point: 250-252 °C
• Boiling Point: 464.6°Cat760mmHg
• PKA: 4.81±0.70(Predicted)
• Flash Point: 248.9°C
• PSA: 57.53000
• Density: 1.13g/cm³
• LogP: 4.09080
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 503

Purity/Quality:

99% ^*data from raw suppliers

5ALPHA-ETIANIC ACID 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4C(=O)O)C)O

Technology Process of 3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid

There total 27 articles about 3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 3β,17α-dihydroxy-5α-pregnan-20-one (570-54-7) + 3β-hydroxy-5α-etianic acid (15173-54-3)

Guidance literature:

With pyridine; trichlorophosphate; Behandeln des Reaktionsgemisches mit OsO₄ in Aether, Erhitzen des Reaktionsprodukts mit Aethanol und wss.Na₂SO₃ und Behandeln einer methanol.Loesung des danach isolierten Reaktionsprodukts mit wss.Perjodsaeure;

DOI:10.1002/hlca.194102401100

Reference yield:

pyridine (110-86-1) + 3,21-diacetoxy-20-methyl-5-pregnan-20-ol + trichlorophosphate (10025-87-3,12599-09-6,63736-95-8,39380-77-3) → 3β,17α-dihydroxy-5α-pregnan-20-one (570-54-7) + 3β-hydroxy-5α-etianic acid (15173-54-3)

Guidance literature:

3β,21-diacetoxy-20ξ-methyl-5α-pregnan-20ξ-ol of mp: 190 degree; Reaktion ueber mehrere Stufen;

DOI:10.1002/hlca.194102401100

Reference yield:

pregnenolone acetate (906-83-2) → androstanedione (846-46-8) + 3β-hydroxy-5α-etianic acid (15173-54-3)

Guidance literature:

With dipotassium peroxodisulfate; sulfuric acid; acetic acid; Erhitzen des Reaktionsprodukts mit aethanol. KOH und Behandeln der neutralen Anteile des danach erhaltenen Reaktionsprodukts mit CrO₃ in wss. Essigsaeure bei 25grad;

DOI:10.1021/ja01860a062

upstream raw materials:

3β-acetoxy-5α.14β-androstane-17α-carboxylic acid methyl ester

3β-acetoxy-21-nor-5α-pregnadien-(14.16)-oic acid-(20)-methyl ester

methyl 3β-acetoxy-5α-androst-16-ene-17-carboxylate

pregnenolone acetate

Downstream raw materials:

5α-etianic acid

5α.14β-androstane-carboxylic acid-(17α)-methyl ester

methyl-5α-etianate

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS". Paragraph 0579; 0580. . Retrieved 2021/01/23.
• 2、 Pouzar, Vladimir,Havel, Miroslav. "Absolute configuration at C(20) of the derivatives of 21-nor-5α-cholane-20,24-diol". . p. 2443 - 2451. Retrieved 2007/10/02.