(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase编号: 72986
• 分子式: C29H48O
• 平均质量: 412.69082
• 单一同位素质量: 412.37051616
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](/C=C/[C@@H](CC)C(C)C)C)C)O
• Canonical SMILES: CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
• InChI: InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: HCXVJBMSMIARIN-PHZDYDNGSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
• IUPAC传统名: stigmasterol
• 别名: 3β-羟基-24-乙基-5,22-胆甾二烯; 5,22-豆甾二烯-3β-醇; 豆固醇; 豆甾醇; Stigmasterol; Stigmasterin; Beta-Stigmasterol; Stigmasterol; Stigmasta-5,22-dien-3-ol; (3β,22E)-Stigmasta-5,22-dien-3-ol; Stigmasta-5,22-dien-3β-ol; 24-Ethyl-5,22-cholestadien-3β-ol; 24β-Ethyl-5,22-cholestadien-3β-ol; NSC 8095

登记号

• CAS号: 83-48-7
• EC号: 201-482-7
• MDL号: MFCD00003630
• Beilstein号: 2568182
• PubChem SID: 162037906; 24899523
• PubChem CID: 5280794

理论计算性质

• Acid pKa: 18.20429
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 7.482555
• LogD (pH = 7.4): 7.482555
• Log P: 7.482555
• 摩尔折射率: 130.8827 cm^3
• 极化性: 51.43686 Å^3
• 极化表面积: 20.23 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform
• 外观: Cryst.; White Solid
• 熔点: 151-153°C; 165-167 °C(lit.)

安全信息

• 保存条件: -20°C; Refrigerator
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... POLA1(5422), TOP2A(7153)rat ... Polb(29240)

产品相关信息

• 纯度: ~95%
• 成盐信息: Free Base

详细说明

Selleck Chemicals - S2361

Research Area: Metabolic Disease
Biological Activity:
Stigmasterol(Stigmasterin) is used as a precursor in the manufacture of synthetic progesterone, a valuable human hormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D3. Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate, breast, and colon cancers. [1]

Sigma Aldrich - S2424

包装
1 g in poly tube
5, 10, 25 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S2424.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - S686750

Plant sterol, used as a precursor in the synthesis of progesterone.

参考文献

• http://en.wikipedia.org/wiki/Stigmaste
• Han, P., et al.: Biotechnol. App. Biochem., 54, 105 (2009)
• Matsunaga, I., et al.: Anal. Biochem., 393, 222 (2009)
• Huang, C., et al.: Plant Physiol., 150, 1192 (2009)