Tetrahydrocortisone

Base Information

• Chemical Name: Tetrahydrocortisone
• CAS No.: 53-05-4
• Molecular Formula: C21H32 O5
• Molecular Weight: 364.482
• European Community (EC) Number: 200-161-9
• NSC Number: 76984
• UNII: 5HF9TM2D15
• DSSTox Substance ID: DTXSID70878591
• Nikkaji Number: J4.138F
• Wikipedia: Tetrahydrocortisone
• Wikidata: Q7706546
• Metabolomics Workbench ID: 49820
• ChEMBL ID: CHEMBL1908043
• Mol file: 53-05-4.mol

Synonyms:Tetrahydrocortisone

Chemical Property of Tetrahydrocortisone

Chemical Property:

• Melting Point: 190°
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 544.5°Cat760mmHg
• PKA: 12.38±0.70(Predicted)
• Flash Point: 297.1°C
• PSA: 94.83000
• Density: 1.249g/cm³
• LogP: 1.86150
• Storage Temp.: Refrigerator
• Solubility.: Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 364.22497412
• Heavy Atom Count: 26
• Complexity: 632

Purity/Quality:

99% ^*data from raw suppliers

TetrahydroCortisone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
• Recent ClinicalTrials: Preemptive Infiltration With Betamethasone and Ropivacaine for Postoperative Pain in Laminoplasty or Laminectomy
• Uses: Cortisone (C696500) derivative. A normal mammalian metabolite of Cortisone (C696500).

Technology Process of Tetrahydrocortisone

There total 12 articles about Tetrahydrocortisone 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:

21-bromo-3α,17-dihydroxy-5β-pregnane-11,20-dione (95044-38-5) → tetrahydrocortisone (53-05-4)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01122a060

Reference yield:

3α,17-dihydroxy-5β-pregnane-11,20-dione (641-78-1) → tetrahydrocortisone (53-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dioxane; bromine

2: aq.-ethanolic NaOH

With 1,4-dioxane; sodium hydroxide; bromine;

DOI:10.1021/ja01122a060

Reference yield:

(17Ξ)-3α,11,20-triacetoxy-5β-pregna-9(11),17(20)-diene (115484-65-6) → tetrahydrocortisone (53-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: peroxybenzoic acid; benzene / Behandeln des Reaktionsprodukts mit wss.-aethanol.NaOH

2: dioxane; bromine

3: aq.-ethanolic NaOH

With 1,4-dioxane; sodium hydroxide; Perbenzoic acid; bromine; benzene;

DOI:10.1021/ja01122a060

upstream raw materials:

Cortisone

21-bromo-3α,17-dihydroxy-5β-pregnane-11,20-dione

17,21-dihydroxy-11,20-dioxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid

3α,17-dihydroxy-5β-pregnane-11,20-dione

Downstream raw materials:

5β-dihydrocortisone

((3R,5R,8S,9S,10S,13S,14S,17R)-3,17-Dihydroxy-10,13-dimethyl-11-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-hydroxy-acetic acid