7alpha-Hydroxydehydroepiandrosterone

Base Information

• Chemical Name: 7alpha-Hydroxydehydroepiandrosterone
• CAS No.: 53-00-9
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43
• UNII: CL15H93XTM
• DSSTox Substance ID: DTXSID901018916
• Nikkaji Number: J575.713D
• Wikipedia: 7%CE%B1-Hydroxy-DHEA
• Wikidata: Q27155401
• Metabolomics Workbench ID: 35379
• ChEMBL ID: CHEMBL1079392
• Mol file: 53-00-9.mol

Synonyms:7 alpha-hydroxydehydroepiandrosterone;7-hydroxydehydroepiandrosterone;7-hydroxydehydroepiandrosterone, (3beta)-isomer;7-hydroxydehydroepiandrosterone, (3beta,7beta)-isomer;7beta-hydroxydehydroepiandrosterone;7beta-OH-DHEA

Chemical Property of 7alpha-Hydroxydehydroepiandrosterone

Chemical Property:

• Vapor Pressure: 6.04E-11mmHg at 25°C
• Melting Point: 181.5-183.5 °C(Solv: acetone (67-64-1))
• Refractive Index: 1.578
• Boiling Point: 473.3 °C at 760 mmHg
• PKA: 14.06±0.70(Predicted)
• Flash Point: 254.1 °C
• PSA: 57.53000
• Density: 1.19 g/cm³
• LogP: 2.85000
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 304.20384475
• Heavy Atom Count: 22
• Complexity: 539

Purity/Quality:

99% ^*data from raw suppliers

Hydroxydehydroepiandrosterone ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)C(C=C4C3(CCC(C4)O)C)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O
• Uses: 7α-Hydroxydehydroepiandrosterone (7α-OH DHEA) is the main metabolite of Dehydroepiandrosterone (DHEA) (D229585).

Technology Process of 7alpha-Hydroxydehydroepiandrosterone

There total 51 articles about 7alpha-Hydroxydehydroepiandrosterone 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: 89.0%

7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate (37976-94-6,517894-20-1) → 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1,7522-54-5,62357-03-3,53-00-9)

Guidance literature:

With sodium carbonate; In methanol; water; for 1.25h; Heating;

DOI:10.1016/j.steroids.2005.04.002

Reference yield: 88.0%

dehydroepiandrosterone (53-43-0) → 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1,7522-54-5,62357-03-3,53-00-9)

Guidance literature:

With D-glucose; In acetone; at 20 ℃; for 24h;

DOI:10.1016/j.steroids.2010.08.001

Reference yield: 81.0%

Benzoic acid (3S,7S,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl ester → 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1,7522-54-5,62357-03-3,53-00-9)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/j.tetasy.2005.08.024

upstream raw materials:

3-O-acetyl-7α-OH-DHEA

dehydroepiandrosterone

prasterone acetate

7α-hydroxy-17-oxoandrost-5-ene-3β-yl acetate

Downstream raw materials:

3β,7α-diacetoxyandrost-5-en-17-one

3beta,17beta-Dihydroxyandrost-5-en-7-one

3β-O-(1,2-dipalmitoyl-sn-glycero-3-phospho)-7α-hydroxy-androst-5-en-17-one

5-androstene-3β-ol-7,17-dione

Refernces

• 1、 Cao, Yang,Chen, Wenyu,Fisher, Matthew J.,Leung, Aaron,Wong, Luet L.. "Oxidative Diversification of Steroids by Nature-Inspired Scanning Glycine Mutagenesis of P450BM3 (CYP102A1)". . p. 8334 - 8343. Retrieved 2020/09/18.
• 2、 Peart, Patrice C.,Reynolds, William F.,Reese, Paul B.. "The generation of a steroid library using filamentous fungi immobilized in calcium alginate Dedicated to the memory of Professor Sir John W. Cornforth, University of Sussex (1917-2013).". . p. 16 - 24. Retrieved 2016/01/25.