3alpha-Hydroxytibolone

Base Information

• Chemical Name: 3alpha-Hydroxytibolone
• CAS No.: 100239-44-9
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.46
• UNII: 37T303O94A
• DSSTox Substance ID: DTXSID001315905
• Nikkaji Number: J826.154G
• Wikipedia: 3%CE%B1-Hydroxytibolone
• Mol file: 100239-44-9.mol

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

Chemical Property of 3alpha-Hydroxytibolone

Chemical Property:

• Melting Point: 72-74°C
• Refractive Index: 1.578
• PSA: 40.46000
• LogP: 3.67440
• Storage Temp.: Controlled Substance, -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

3a-Hydroxytibolone ^*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: As a metabolite of Tibolone, 3α-Hydroxy Tibolone can be used as a synthetic steroid with weak estrogenic, androgenic and progestogenic activity and a pharamceutical used in the treatment of menopausal syndrome.

Technology Process of 3alpha-Hydroxytibolone

There total 5 articles about 3alpha-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: 95.0%

17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-α3-yl acetate (500019-09-0) → 3alpha-Hydroxytibolone (100239-44-9)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃; for 3h;

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

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:

tibolone (5630-53-5) → 3alpha-Hydroxytibolone (100239-44-9)

Guidance literature:

With D-glucose; Kluyveromyces lactis CBS 2359; In phosphate buffer; at 28 ℃; for 48h; pH=6.0;

DOI:10.1016/j.steroids.2007.09.008

upstream raw materials:

tibolone

17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-α3-yl acetate

17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-ξ3-yl acetate

17α-ethynyl-7α-methyl-5(10)-estren-3ξ,17β-diol

Downstream raw materials:

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

3α-tibolol-3-yl (R)-2-methoxy-2-phenylpent-3-ynoate

(3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol

Refernces

• 1、 Ferraboschi, Patrizia,Colombo, Diego,Reza-Elahi, Shahrzad. "A practical chemoenzymatic approach to the synthesis of 3-hydroxy metabolites of tibolone". . p. 2583 - 2586. Retrieved 2002.
• 2、 -. "Method of producing tibolone metabolites by fermentation with Rhizopus stolonifer". Page/Page column 12. . Retrieved 2012/04/10.