Teasterone

Base Information

• Chemical Name: Teasterone
• CAS No.: 92751-21-8
• Molecular Formula: C28H48O4
• Molecular Weight: 448.67832
• UNII: O8HW7BJ06G
• DSSTox Substance ID: DTXSID1041136
• Metabolomics Workbench ID: 34784
• Nikkaji Number: J417.942K
• Wikidata: Q27109923
• Mol file: 92751-21-8.mol

Synonyms:Teasterone;92751-21-8;O8HW7BJ06G;UNII-O8HW7BJ06G;(3beta,5alpha,22R,23R,24S)-3,22,23-trihydroxyergostan-6-one;Ergostan-6-one, 3,22,23-trihydroxy-, (3SS,5a,22R,23R,24S)-;6-oxo-5alpha-campestan-3beta,22R,23R-triol;(3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one;DTXSID1041136;CHEBI:26863;LMST01030121;6-oxo-campestan-3beta,22R,23R-triol;Q27109923;(22R,23R)-3beta,22,23-trihydroxy-5alpha-campestan-6-one;(22R,23R,24S)-3beta,22,23-trihydroxy-5alpha-ergostan-6-one;(3.BETA.,5.ALPHA.,22R,23R,24S)-3,22,23-TRIHYDROXYERGOSTAN-6-ONE

Chemical Property of Teasterone

Chemical Property:

• Melting Point: 200 - 201 °C (ethyl acetate)
• PSA: 77.76000
• LogP: 4.83520
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 448.35526001
• Heavy Atom Count: 32
• Complexity: 706

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2CC(=O)C4C3(CCC(C4)O)C)C)O)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC(=O)[C@@H]4[C@@]3(CC[C@@H](C4)O)C)C)[C@H]([C@@H]([C@@H](C)C(C)C)O)O

Technology Process of Teasterone

There total 5 articles about Teasterone 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: 98.0%

(22R,23R,24S)-6-oxo-5α-ergostane-3β,22,23-triol triacetate (108160-30-1) → teasterone (92751-21-8)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Heating;

Reference yield:

3-dehydroteasterone (124853-28-7) → typhasterol (87734-68-7) + teasterone (92751-21-8)

Guidance literature:

In dimethyl sulfoxide; for 24h; Product distribution; lily cell culture; biotransformation of 3-oxoteasterone, epimerization of teasterone into typhasterol;

Reference yield:

(22E,24S)-6-oxo-5α-ergost-22-en-3β-yl acetate (108266-22-4) → teasterone (92751-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 15 h / Ambient temperature

2: 1.) 30 percent hydrobromic acid, 2.) 80 percent acetic acid, 3.) pyridine

3: 98 percent / 5 percent KOH / methanol / 1 h / Heating

With pyridine; potassium hydroxide; hydrogen bromide; acetic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

upstream raw materials:

3-dehydroteasterone

(22R,23R,24S)-6-oxo-5α-ergostane-3β,22,23-triol triacetate

(22E,24S)-6-oxo-5α-ergost-22-en-3β-yl acetate

Δ²²-6-oxocampestanol

Downstream raw materials:

typhasterol

(22R,23R,24S)-22,23-isopropylidenedioxy-6-oxo-5α-ergostan-3β-yl methanesulphonate