Dihydrocortisol

Base Information

• Chemical Name: Dihydrocortisol
• CAS No.: 1482-50-4
• Molecular Formula: C21H32 O5
• Molecular Weight: 364.482
• DSSTox Substance ID: DTXSID101317085
• Nikkaji Number: J39.546C
• Wikidata: Q27105345
• Metabolomics Workbench ID: 35481
• Mol file: 1482-50-4.mol

Synonyms:Dihydrocortisol;1482-50-4;5-beta-Dihydrocortisol;5beta-dihydrocortisol;5|A-Dihydrocortisol;11-beta,17,21-Trihydroxy-5-beta-pregnane-3,20-dione;(5R,8S,9S,10S,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;(5R,8S,9S,10S,11S,13S,14S,17R)-11,17-Dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one;11beta,17alpha,21-Trihydroxy-5beta-pregnane-3,20-dione;11,17,21-Trihydroxypregnane-3,20-dione (5bet,11beta)-;(5beta,11beta)-11,17,21-Trihydroxypregnane-3,20-dione;5-beta-Pregnane-3,20-dione, 11-beta,17,21-trihydroxy-;Pregnane-3,20-dione, 11,17,21-trihydroxy-, (5beta,11beta)-;11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;4,5beta-Dihydrocortisol;5 beta -Dihydrocortisol;CHEBI:732;SCHEMBL517666;Pregnane-3,20-dione, 11,17,21-trihydroxy-, (5beta,11beta)- (9CI);DTXSID101317085;HY-N3995;LMST02030204;NSC 15473;MS-25817;LS-118553;CS-0146622;C05471;5beta-Pregnane-11beta,17alpha,21-triol-3,20-dione;Q27105345

Chemical Property of Dihydrocortisol

Chemical Property:

• Boiling Point: 544.5°Cat760mmHg
• Flash Point: 297.1°C
• PSA: 94.83000
• Density: 1.249g/cm³
• LogP: 1.86150
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• 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:

97% ^*data from raw suppliers

5β-Dihydrocortisol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)CC1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
• General Description: 11-BETA,17-ALPHA,21-TRIHYDROXY-5-BETA-PREGNANE-3,20-DIONE (5β-dihydrocortisol, Dhc) is a reduced metabolite of cortisol that exhibits binding interactions with human serum albumin (HSA) and demonstrates cytotoxic effects on breast cancer cells (MCF-7) while showing lower toxicity toward normal kidney cells (HEK293), suggesting potential anticancer activity.

Technology Process of Dihydrocortisol

There total 16 articles about Dihydrocortisol 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: 100.0%

HYDROCORTISONE (50-23-7) → 5β-pregnane-11β,17α,21-triol-3,20-dione (1482-50-4,71973-95-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In N,N-dimethyl-formamide; at 30 ℃; under 2585.81 Torr;

Reference yield: 86.0%

HYDROCORTISONE (50-23-7) → 11β,17α,21-trihydroxy-5α-pregnane-3,20-dione (516-41-6,71973-95-0) + 5β-pregnane-11β,17α,21-triol-3,20-dione (1482-50-4,71973-95-0)

Guidance literature:

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon; In ethanol; at 80 ℃; for 6h;

DOI:10.1080/07391102.2018.1433554

Reference yield: 69.6%

17α-21-dihydroxy-5-α-pregnane-3,20-dione (312-99-2) → 11α,17α,21-trihydroxy-5α-pregnane-3,20-dione (516-41-6,1482-50-4,16355-27-4,127182-47-2,71973-95-0)

Guidance literature:

C_. blakesleea culture;

DOI:10.1007/BF00764822

upstream raw materials:

RU 18760

HYDROCORTISONE

NADPH

hydrocortisone acetate

Downstream raw materials:

11β-hydroxyetiocholanolone

5β-androstane-3,11,17-trione

RU 18760

tetrahydrocortisol