Stanolone

Base Information

• Chemical Name: Stanolone
• CAS No.: 521-18-6
• Deprecated CAS: 12040-51-6,28801-96-9,1050679-06-5,28801-96-9
• Molecular Formula: C19H30O2
• Molecular Weight: 290.446
• European Community (EC) Number: 208-307-3
• NSC Number: 10972
• UNII: 08J2K08A3Y
• DSSTox Substance ID: DTXSID9022364
• Nikkaji Number: J39.503J
• Wikipedia: Dihydrotestosterone,Androstanolone
• Wikidata: Q411054
• NCI Thesaurus Code: C72098
• Pharos Ligand ID: FSL18YVLA51P
• Metabolomics Workbench ID: 35332
• ChEMBL ID: CHEMBL27769
• Mol file: 521-18-6.mol

Synonyms:5a-Androstan-3-one, 17b-hydroxy- (8CI);(+)-Androstan-17b-ol-3-one;17b-Hydroxy-3-androstanone;17b-Hydroxy-5a-androstan-3-one;17b-Hydroxy-5a-androstane-3-one;4,5a-Dihydrotestosterone;4-Dihydrotestosterone;5a,17b-Hydroxyandrostan-3-one;5a-Androstan-17b-ol-3-one;5a-Androstanolone;5a-Dihydrotestosterone;Anaboleen;Anabolex;Andractim;Androlone;Androstan-17b-ol-3-one;Androstanolone;Cristerona MB;DHT;Dihydrotestosterone;LG 152;NSC 10972;Neodrol;Stanaprol;Testosterone, dihydro-;

Chemical Property of Stanolone

Chemical Property:

• Appearance/Colour: US DEA Schedule III
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Melting Point: 173-183 °C
• Refractive Index: 1.536
• Boiling Point: 413.1 °C at 760 mmHg
• PKA: 15.08±0.60(Predicted)
• Flash Point: 176.4 °C
• PSA: 37.30000
• Density: 1.085 g/cm³
• LogP: 3.95910
• Storage Temp.: Controlled Substance, -20°C Freezer
• Water Solubility.: 344.3g/L(temperature not stated)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 290.224580195
• Heavy Atom Count: 21
• Complexity: 459

Purity/Quality:

99.9% ^*data from raw suppliers

Dihydrotestosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 61-40-39/23/24/25-23/24/25-11
• Safety Statements: 53-36/37/39-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4O)C
• Isomeric SMILES: C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
• Recent ClinicalTrials: Effect of Dihydrotestosterone (DHT) on Prostate Tissue [Short Title: DHT-3]
• Description: Stanolone is well known as dihydrotestosterone (DHT), which is an endogenous androgen sex steroid and hormone. It is an agonist of the androgen receptor (AR). It plays important physiological role in sexual differentiation, maturation of the penis and scrotum, hair, sebum production and development and maintenance of the prostate gland and seminal vesicles. It is mainly used for the treatment of male hypogonadism, androgen deficiency of severe illness, androgen deficiency of ageing and microphallus in infancy.
• Uses: Stanolone is a potent androgenic metabolite of testosterone that It is Controlled substance. It was created for the treatment of muscle wasting disease, and osteoporosis. It is a powerful anabolic steroid, which is similar to the body's naturally produced Dihydrotestosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid.
• Therapeutic Function: Androgen

Technology Process of Stanolone

There total 65 articles about Stanolone 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%

testosterone (58-22-0) → Stanolone (521-18-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at -20 ℃; for 8h; under 1500.15 Torr;

Reference yield: 97.5%

17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one (58701-44-3) → Stanolone (521-18-6)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 3h;

DOI:10.1016/j.steroids.2012.09.003

Reference yield: 95.0%

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol (1046-35-1) → Stanolone (521-18-6)

Guidance literature:

With diiodosilane; In chloroform; at -42 ℃; for 0.166667h;

DOI:10.1055/s-1991-26533

upstream raw materials:

testosterone

androstanedione

17β-hydroxy-5α-androstan-3-one semicarbazone

5alpha-Androstane-3beta,17beta-diol-17-hexahydrobenzoate

Downstream raw materials:

dihydrotestosterone p-chlorophenoxyisobutyrate

2-(4-Chloro-phenoxy)-2-methyl-propionic acid (5S,10R,13S,17S)-3-[2-(4-chloro-phenoxy)-2-methyl-propionyloxy]-10,13-dimethyl-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

17β-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androstan-3-one

3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene

Refernces

• 1、 Ranjan, Mala,Diffley, Penny,Stephen, Gita,Price, David,Walton, Terence J.,Newton, Russell P.. "Comparative study of human steroid 5α-reductase isoforms in prostate and female breast skin tissues: Sensitivity to inhibition by finasteride and epristeride". . p. 115 - 126. Retrieved 2002.
• 2、 Holland, Herbert L.,Xu, Weili,Hughes, Donald W.. "Stereochemistry of Reduction by the 5α-Reductase Enzyme of Penicillium decumbens and the 1H NMR Assignment of 5α-Dihydrotestosterone". . p. 1760 - 1761. Retrieved 1989.
• 3、 Ruzicka,Goldberg,Grob. "". . p. 1151,1153. Retrieved 1941.
• 4、 Cobice, Diego F.,Livingstone, Dawn E. W.,MacKay, C. Logan,Goodwin, Richard J. A.,Smith, Lee B.,Walker, Brian R.,Andrew, Ruth. "Spatial Localization and Quantitation of Androgens in Mouse Testis by Mass Spectrometry Imaging". . p. 10362 - 10367. Retrieved 2016.
• 5、 Boutin, Sophie,Roy, Jenny,Maltais, René,Poirier, Donald. "Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells – Identifying inhibitors of non-classical pathways producing the most potent androgen". supporting information. . Retrieved 2019/11/26.
• 6、 Yao, Yunxin,Zhao, Guangkuan,Hamze, Abdallah,Alami, Mouad,Provot, Olivier. "Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN". . p. 5775 - 5779. Retrieved 2020/08/17.