Tetrahydrodeoxycortisol

Base Information

• Chemical Name: Tetrahydrodeoxycortisol
• CAS No.: 68-60-0
• Molecular Formula: C21H34 O4
• Molecular Weight: 350.499
• European Community (EC) Number: 200-691-0
• NSC Number: 53901
• DSSTox Substance ID: DTXSID001018945
• Nikkaji Number: J39.545E
• Wikidata: Q27116008
• Metabolomics Workbench ID: 36986
• Mol file: 68-60-0.mol

Synonyms:3 alpha, 17,21-trihydroxy-5 beta-pregnan-20-one;3alpha,5beta-THS;5 beta-pregnane-3alpha,17alpha,21-triol-20-one;tetrahydro compound S;tetrahydro-11-deoxycortisol;tetrahydro-Reichstein's substance S;tetrahydrodeoxycortisol;trihydroxypregnanone

Chemical Property of Tetrahydrodeoxycortisol

Chemical Property:

• Vapor Pressure: 2.55E-12mmHg at 25°C
• Melting Point: 224-226 °C
• Boiling Point: 505.1°C at 760 mmHg
• PKA: 12.65±0.70(Predicted)
• Flash Point: 273.4°C
• PSA: 77.76000
• Density: 1.186g/cm³
• LogP: 2.68250
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 350.24570956
• Heavy Atom Count: 25
• Complexity: 562

Purity/Quality:

98%min ^*data from raw suppliers

Tetrahydro-11-deoxyCortisol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O

Technology Process of Tetrahydrodeoxycortisol

There total 30 articles about Tetrahydrodeoxycortisol 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: 78.0%

3β,21-diacetoxy-5α-pregnan-17α-ol-20-one (6003-22-1) → 3β,5α-Tetrahydro Reichstein's Substance S (68-60-0,601-01-4,601-03-6,7635-25-8,7694-32-8,97170-01-9,516-47-2)

Guidance literature:

With water; potassium hydroxide; In methanol; for 2h;

DOI:10.1016/j.steroids.2011.01.006

Reference yield: 75.0%

21-acetoxy-3α,17α-dihydroxy-5β-pregnan-20-one (16065-01-3) → tetrahydrodeoxycortisol (68-60-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1.5h;

DOI:10.1248/cpb.58.344

Reference yield: 34.0%

Cortexolone (152-58-9) → 3β,5α-Tetrahydro Reichstein's Substance S (68-60-0,601-01-4,601-03-6,7635-25-8,7694-32-8,97170-01-9,516-47-2) + 17α-21-dihydroxy-5-α-pregnane-3,20-dione (312-99-2)

Guidance literature:

In ethanol; at 24 - 26 ℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;

DOI:10.1016/0039-128X(95)00071-W

upstream raw materials:

Cortexolone

5β-pregnan-17α,21-diol-3,20-dione

5β-dihydro-11-deoxycortisol 21-acetate

17,21-dihydroxy-20-oxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid

Downstream raw materials:

androstanedione

(20R)-5α-pregnanetetrol-(3β,17,20,21)

Refernces

• 1、 Okihara, Rika,Mitamura, Kuniko,Hasegawa, Maki,Mori, Megumi,Muto, Akina,Kakiyama, Genta,Ogawa, Shoujiro,Iida, Takashi,Shimada, Miki,Mano, Nariyasu,Ikegawa, Shigeo. "Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5 α- and 5 β-series". experimental part. p. 344 - 353. Retrieved 2011/02/22.
• 2、 -. "Permeable, non-irritating prodrugs of nonsteroidal and steroidal agents". . . Retrieved 2008/06/13.