3beta-Hydroxytibolone

Base Information

• Chemical Name: 3beta-Hydroxytibolone
• CAS No.: 100239-45-0
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.46
• UNII: TEP8IU9GMR
• DSSTox Substance ID: DTXSID301315930
• Nikkaji Number: J826.155E
• Wikipedia: 3%CE%B2-Hydroxytibolone
• Mol file: 100239-45-0.mol

Synonyms:3-hydroxytibolone;3alpha-hydroxytibolone;3alpha-Tib;3beta-hydroxytibolone;3beta-Tib

Chemical Property of 3beta-Hydroxytibolone

Chemical Property:

• Melting Point: 165-169°C
• Refractive Index: 1.578
• Boiling Point: 449.1±45.0 °C(Predicted)
• PKA: 13.10±0.70(Predicted)
• PSA: 40.46000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 3.67440
• Storage Temp.: -20°C Freezer
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 596

Purity/Quality:

99%min ^*data from raw suppliers

3BETA-HYDROXYTIBOLONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=C(CCC(C2)O)C3C1C4CCC(C4(CC3)C)(C#C)O
• Isomeric SMILES: C[C@@H]1CC2=C(CC[C@@H](C2)O)[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
• Uses: 3β-Hydroxy Tibolone is a metabolite of Tibolone. A synthetic steroid with weak estrogenic, androgenic and progestogenic activity. A pharamceutical used in the treatment of menopausal syndrome.

Technology Process of 3beta-Hydroxytibolone

There total 4 articles about 3beta-Hydroxytibolone 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: 70.0%

tibolone (5630-53-5) → 3alpha-Hydroxytibolone (100239-44-9) + (3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol (100239-45-0)

Guidance literature:

With lithium tri(t-butoxy)aluminum hydride; In tetrahydrofuran; at -70 ℃; for 2h;

DOI:10.1002/mrc.1064

Reference yield: 53.0%

Benzoic acid (3S,7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-2,3,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester → (3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol (100239-45-0)

Guidance literature:

With sodium carbonate; In methanol; water; at 50 ℃; for 4h;

DOI:10.1002/mrc.1064

Reference yield:

tibolone (5630-53-5) → (3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol (100239-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DIBAL / toluene / 3 h / 0 °C

2: 0.24 g / Candida antarctica lipase Novozym 435 / toluene / 1 h / 30 °C

With Candida antarctica lipase Novozym 435; diisobutylaluminium hydride; In toluene;

DOI:10.1016/S0957-4166(02)00712-7

upstream raw materials:

tibolone

3alpha-Hydroxytibolone

Downstream raw materials:

3β-tiboloyl (S)-2-methoxy-2-phenylpent-3-ynoate

3β-tiboloyl (R)-2-methoxy-2-phenylpent-3-ynoate

Refernces

• 1、 Choudhary, M. Iqbal,Shah, S. Adnan Ali,Atta-Ur-Rahman,Khan, Shamsun-Nahar,Khan, Mahmud Tareq Hassan. "Alpha-glucosidase and tyrosinase inhibitors from fungal hydroxylation of tibolone and hydroxytibolones". experimental part. p. 956 - 966. Retrieved 2010/10/05.
• 2、 Romano, Diego,Ferrario, Valerio,Mora, Diego,Lenna, Roberto,Molinari, Francesco. "Enantioselective production of 3-hydroxy metabolites of tibolone by yeast reduction". . p. 112 - 115. Retrieved 2008/03/30.