7b-Hydroxydehydroepiandrosterone

Base Information

• Chemical Name: 7b-Hydroxydehydroepiandrosterone
• CAS No.: 2487-48-1
• Molecular Formula: C19H28O3
• Molecular Weight: 304.43
• UNII: 923RBW7OJQ
• DSSTox Substance ID: DTXSID50431284
• Nikkaji Number: J1.053.197G
• Wikipedia: 7%CE%B2-Hydroxy-DHEA
• Wikidata: Q27271468
• Metabolomics Workbench ID: 35384
• ChEMBL ID: CHEMBL1082098
• Mol file: 2487-48-1.mol

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

Chemical Property of 7b-Hydroxydehydroepiandrosterone

Chemical Property:

• Melting Point: 215-216 °C(Solv: acetone (67-64-1); cyclohexane (110-82-7))
• Boiling Point: 473.271 °C at 760 mmHg
• PKA: 14.06±0.70(Predicted)
• Flash Point: 254.138 °C
• PSA: 57.53000
• Density: 1.194 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:

98%,99%, ^*data from raw suppliers

7β-HydroxyDehydroEpiandrosterone(1.0mg/mLinAcetonitrile) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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: 7β-Hydroxydehydroepiandrosterone (7β-OH DHEA) is the main metabolite of Dehydroepiandrosterone (DHEA) (D229585).

Technology Process of 7b-Hydroxydehydroepiandrosterone

There total 86 articles about 7b-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: 71.2%

dehydroepiandrosterone (53-43-0) → 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1,7522-54-5,62357-03-3,53-00-9) + 3β,7α,15α-trihydroxy-5-androstene-17-one (2963-69-1)

Guidance literature:

With randomly methylated β-cyclodextrin; In water; N,N-dimethyl-formamide; at 29 ℃; for 30h; pH=6.0;

DOI:10.1016/j.steroids.2008.10.019

upstream raw materials:

3-O-acetyl-7α-OH-DHEA

dehydroepiandrosterone

prasterone acetate

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

Downstream raw materials:

Carbonic acid (3S,7R,10R,13S)-7-methoxycarbonyloxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester methyl ester

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

5-androstene-3β-ol-7,17-dione

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

Refernces

• 1、 Shan, Lihong,Jiao, Kai,Yin, Minghui,Huang, Jiajia,Chen, Yanjie,Qin, Shangshang,Liu, Hongmin. "Biotransformation of 5-en-3β-ol steroids by Mucor circinelloides lusitanicus". . p. 83 - 88. Retrieved 2016.
• 2、 Crabb,Dawson,Williams. "Microbiological transformations of 3β acetoxy 17α aza D homoandrost 5 en 17 one and 3β acetoxy androst 5 en 17 one with the fungus Cunninghamella elegans". . p. 3623 - 3626. Retrieved 1975.
• 3、 Wu, Yan,Li, Hui,Lu, Zhen-Ming,Li, Heng,Rao, Zhi-Ming,Geng, Yan,Shi, Jin-Song,Xu, Zheng-Hong. "Enhancement of steroid hydroxylation yield from dehydroepiandrosterone by cyclodextrin complexation technique". . p. 70 - 77. Retrieved 2014.
• 4、 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.