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

• ChemBase编号: 118956
• 分子式: C19H30O2
• 平均质量: 290.4403
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: dihydrotestosterone
• 别名: 4,5α-双氢睾酮; 加氢睾酮; 雄烯醇酮; 雄诺龙; 5α-二氢睾酮; (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

登记号

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

理论计算性质

• Acid pKa: 19.377705
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.4112575
• LogD (pH = 7.4): 3.4112577
• Log P: 3.4112577
• 摩尔折射率: 83.6031 cm^3
• 极化性: 33.49998 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Chloroform; Ether; Ethyl Acetate
• 外观: White Solid
• 熔点: 177-1810C

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: BV8052000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 61-40
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H351-H360
• GHS警示性声明: P201-P281-P308 + P313
• 个人保护装置: 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
• 毒品管制信息: 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

药理学性质

• 相关基因信息: 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)

产品相关信息

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

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A637540

Anabolic steroid. Controlled substance.

参考文献

• 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)