Epiandrosterone acetate

Base Information

• Chemical Name: Epiandrosterone acetate
• CAS No.: 1239-31-2
• Molecular Formula: C21H32O3
• Molecular Weight: 332.483
• Hs Code.: 2937290090
• European Community (EC) Number: 214-612-2,623-940-9
• DSSTox Substance ID: DTXSID601305364
• Nikkaji Number: J393.512D
• Metabolomics Workbench ID: 199010
• ChEMBL ID: CHEMBL4632363
• Mol file: 1239-31-2.mol

Synonyms:Epiandrosterone acetate;1239-31-2;Isoandrosterone acetate;3beta-Acetoxy-5alpha-androstan-17-one;epi-Androsterone acetate;NSC 120612;BRN 2625063;Androstan-17-one, 3-(acetyloxy)-, (3beta,5alpha)-;17-Oxo-5alpha-androstan-3beta-yl acetate;5alpha-Androstan-3beta-ol-17-one acetate;Androstan-17-one, 3-(acetyloxy)-, (3b,5a)-;(3-beta,5-alpha)-3-(Acetyloxy)androstan-17-one;Androsterone acetate;ANDROSTEN-17-ONE, 3-beta-HYDROXY-, ACETATE;4-08-00-00644 (Beilstein Handbook Reference);5alpha-Androstan-17-one, 3beta-hydroxy-, acetate;5.alpha.-Androstan-17-one, 3.beta.-hydroxy-, acetate;Androstan-17-one, 3-(acetyloxy)-, (3.beta.,5.alpha.)-;SCHEMBL1114494;CHEMBL4632363;3b-acetoxy-5a-androstan-17-one;DTXSID601305364;BCP10734;MFCD00067127;AKOS015913420;KS-5201;[(3S,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate;LS-19499;3-beta-Acetoxy-5-alpha-Androstan-17-one;(3-beta,5-alpha)-17-Oxoandrostan-3-yl acetate;J-005001;(3aS,3bR,5aS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-1-oxo-hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate;(3S,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate;Acetic acid (3S,5S,8R,10S,13S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Chemical Property of Epiandrosterone acetate

Chemical Property:

• Vapor Pressure: 9.24E-08mmHg at 25°C
• Melting Point: 169-173 °C
• Refractive Index: 1.54
• Boiling Point: 424.6 °C at 760 mmHg
• Flash Point: 182.8 °C
• PSA: 43.37000
• Density: 1.09 g/cm³
• LogP: 4.52990
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 555

Purity/Quality:

99% ^*data from raw suppliers

Epiandrosteroneacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 16-23-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C(C1)CCC3C2CCC4(C3CCC4=O)C)C
• Isomeric SMILES: CC(=O)O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)C
• Uses: Hormone.

Technology Process of Epiandrosterone acetate

There total 76 articles about Epiandrosterone acetate 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: 99.0%

Epiandrosterone (481-29-8) + acetic anhydride (108-24-7) → 3β-acetoxy-5α-androstan-17-one (1239-31-2)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.jfluchem.2008.04.010

Reference yield: 96.0%

Epiandrosterone (481-29-8) + acetyl chloride (75-36-5) → 3β-acetoxy-5α-androstan-17-one (1239-31-2)

Guidance literature:

With triethylamine; In dichloromethane; Inert atmosphere;

DOI:10.1021/acsmedchemlett.0c00106

Reference yield: 95.0%

Epiandrosterone (481-29-8) + acetic acid 2,4-difluorophenyl ester (36914-77-9) → 3β-acetoxy-5α-androstan-17-one (1239-31-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c03017

upstream raw materials:

3α-chloro-5αH-androstan-17-one

potassium acetate

prasterone acetate

acetic acid-[20-methyl-5α-pregnen-(17(20))-yl-(3β)-ester]

Downstream raw materials:

3beta-7alpha-Dihydroxy-5alpha-androstane-17-one

3beta-7beta-Dihydroxy-5alpha-androstane-17-one

3beta-hydroxy-5alpha-Androstane-7,17-dione

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Refernces

• 1、 Doller,Gros. "Carbon-13 nuclear magnetic resonance spectral data of steroidal vicinal ketols and related compounds". . p. 168 - 172. Retrieved 1991.
• 2、 Purushottamachar, Puranik,Njar, Vincent C.O.. "A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist". . p. 1530 - 1534. Retrieved 2012.
• 3、 Cui, Hai-Wei,Peng, Shihong,Gu, Xiang-Zhong,Chen, Huang,He, Yuan,Gao, Wei,Lv, Fang,Wang, Jin-Hua,Wang, Yan,Xie, Jia,Liu, Ming-Yao,Yi, Zhengfang,Qiu, Wen-Wei. "Synthesis and biological evaluation of D-ring fused 1,2,3-thiadiazole dehydroepiandrosterone derivatives as antitumor agents". . p. 126 - 137. Retrieved 2016.
• 4、 Kratena, Nicolas,Biedermann, Nina,Stojanovic, Biljana,G?schl, Lorenz,Weil, Matthias,Enev, Valentin S.,Gmeiner, Günter,G?rtner, Peter. "Synthesis of a human long-term oxymetholone metabolite". . . Retrieved 2019.
• 5、 Ishida, Naoki,Kawasaki, Tairin,Murakami, Masahiro,Tosaki, Tomohiro. "Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates". supporting information. p. 7683 - 7687. Retrieved 2021/10/12.