(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 118956
• Molecular Formular: C19H30O2
• Molecular Mass: 290.4403
• Monoisotopic Mass: 290.2245802
• SMILES: [C@]12([C@@H]3[C@H]([C@H]4[C@](CC3)([C@H](CC4)O)C)CC[C@H]1CC(=O)CC2)C
• Canonical SMILES: O=C1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
• InChIKey: NVKAWKQGWWIWPM-ABEVXSGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: dihydrotestosterone
• Synonyms: (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one; (5α,17β)-17-Hydroxyandrostan-3-one; Dihydrotestosterone; 5α-Dihydrotestosterone; Androstanolone; 17β-Hydroxy-5α-androstan-3-one; 4,5α-Dihydrotestosterone; Androstanolone; Stanolone; 5α-Androstan-17β-ol-3-one; 4,5α-双氢睾酮; 加氢睾酮; 雄烯醇酮; 雄诺龙; 5α-二氢睾酮

Database IDs

• CAS Number: 521-18-6
• EC Number: 208-307-3
• MDL Number: MFCD00003667
• Beilstein Number: 2056371
• PubChem SID: 162107215; 24891337; 24869668
• PubChem CID: 10635

CALCULATED PROPERTIES

• Acid pKa: 19.377705
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4112575
• LogD (pH = 7.4): 3.4112577
• Log P: 3.4112577
• Molar Refractivity: 83.6031 cm^3
• Polarizability: 33.49998 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ether; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 177-1810C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: BV8052000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61-40
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H351-H360
• GHS Precautionary statements: P201-P281-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: human ... AR(367), ESR1(2099), PGR(5241), SERPINA6(866), SHBG(6462)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890), Nr3c1(24413), Nr3c2(25672), Pgr(25154)

Product Information

• Purity: ≥97.5%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H30O2

DETAILS

Sigma Aldrich - A8380

Application
5α-Androstan-17β-ol-3-one, also referred to as androstanolone or dihydrotestosterone, is an anabolic steroid. Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone, including the development of the male phenotype during embryogenesis and at puberty.
Biochem/physiol Actions
Androstanolone is an anabolic steroid. Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.

Sigma Aldrich - 31573

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A637540

Anabolic steroid. Controlled substance.

REFERENCES

• Schneider, M., et al.: J. Biotechnol., 46, 161 (1996)
• Bao, S., et al.: Biol. Reprod., 62, 616 (1996)
• Imamura, T., et al.: J. Biol. Chem., 280, 20171 (1996)