19,21-Dihydroxypregn-4-ene-3,20-dione

Base Information

• Chemical Name: 19,21-Dihydroxypregn-4-ene-3,20-dione
• CAS No.: 2394-23-2
• Molecular Formula: C21H30 O4
• Molecular Weight: 346.467
• Mol file: 2394-23-2.mol

Synonyms:19-Hydroxy-11-deoxycorticosterone;19,21-Dihydroxypregn-4-ene-3,20-dione;CHEBI:145762;11-deoxy-19-hydroxycorticosterone;11-Desoxy-19-hydroxycorticosterone;19-Hydroxy-11-desoxycorticosterone;19,21-Dihydroxy-4-pregnene-3,20-dione

Chemical Property of 19,21-Dihydroxypregn-4-ene-3,20-dione

Chemical Property:

• Vapor Pressure: 7.46E-14mmHg at 25°C
• Boiling Point: 538.7°Cat760mmHg
• Flash Point: 293.7°C
• PSA: 74.60000
• Density: 1.22g/cm³
• LogP: 2.66830
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 346.21440943
• Heavy Atom Count: 25
• Complexity: 623

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)CO)CCC4=CC(=O)CCC34CO
• Isomeric SMILES: C[C@]12CCC3C(C1CC[C@@H]2C(=O)CO)CCC4=CC(=O)CC[C@]34CO

Technology Process of 19,21-Dihydroxypregn-4-ene-3,20-dione

There total 35 articles about 19,21-Dihydroxypregn-4-ene-3,20-dione 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: 84.0%

19-hydroxycortodoxone (510-65-6) → 19,21-dihydroxypregn-4-ene-3,20-dione (2394-23-2)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at -20 ℃;

DOI:10.1038/s41467-019-11344-0

Reference yield: 73.4%

19,21-dihydroxypregn-4-ene-3,20-dione 21-acetate (6901-40-2) → 19,21-dihydroxypregn-4-ene-3,20-dione (2394-23-2)

Guidance literature:

With potassium carbonate; In methanol; water; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87452-4

Reference yield: 60.6%

Acetic acid 2-methoxy-2-[(8S,9S,10S,13S,14S)-13-methyl-3-oxo-10-(tetrahydro-pyran-2-yloxymethyl)-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-(17Z)-ylidene]-ethyl ester (104494-77-1,104494-86-2) → 19,21-dihydroxypregn-4-ene-3,20-dione (2394-23-2)

Guidance literature:

With hydrogenchloride; In acetone; for 39h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87452-4

upstream raw materials:

progesterone

21-Hydroxyprogesterone

19-hydroxycortodoxone

19,21-dihydroxypregn-4-ene-3,20-dione 21-acetate

Downstream raw materials:

19,21-bis-benzoyloxy-11β-hydroxy-pregn-4-ene-3,20-dione

Refernces

• 1、 HAYANO,DORFMAN. "The conversion of deoxycorticosterone to 19-hydroxy-11-deoxycorticosterone by adrenal homogenate residues.". . p. 289 - 290. Retrieved 1955.
• 2、 NISHIKAWA,HAGIWARA. "Oxidation of steroids by micro?rganisms; 19-hydroxylation of Reichstein's compound S by Corticium sasakii.". . p. 226 - 228. Retrieved 1958.
• 3、 Wang, Junlin,Zhang, Yanan,Liu, Huanhuan,Shang, Yong,Zhou, Linjun,Wei, Penglin,Yin, Wen-Bing,Deng, Zixin,Qu, Xudong,Zhou, Qianghui. "A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids". . . Retrieved 2019/08/02.
• 4、 Terasawa,Okada. "Convenient preparative routes to 19-hydroxy, 19-oxo-, 19-oic-, and 19-nor-deoxycorticosterone". . p. 537 - 545. Retrieved 2007/10/02.