(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

• ChemBase编号: 72928
• 分子式: C29H50O
• 平均质量: 414.7067
• 单一同位素质量: 414.38616622
• 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](CC[C@@H](CC)C(C)C)C)C)O
• Canonical SMILES: CC[C@@H](C(C)C)CC[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/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: KZJWDPNRJALLNS-VJSFXXLFSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC传统名: β-sitosterol
• 别名: α-二氢岩藻甾醇; 22,23-二氢豆甾醇; 24β-乙基胆固醇; 5-豆甾烯-3β-醇; β-谷甾醇; α-Dihydrofucosterol; 24β-Ethylcholesterol; 5-Stigmasten-3β-ol; β-SITOSTEROL; β-Sitosterol; 22,23-Dihydrostigmasterol; Stigmast-5-en-3-ol; β-Sitosterin; Beta-Sitosterol; β-Sitosterol

登记号

• CAS号: 83-46-5
• EC号: 271-413-3; 200-663-8; 201-480-6
• MDL号: MFCD00003631
• Beilstein号: 1916165
• PubChem SID: 24899671; 24899862; 162037848; 24899468; 24870722
• PubChem CID: 222284
• CHEBI ID: 27693
• CHEMBL: 221542
• Chemspider ID: 192962
• 美国药典/FDA物质标识码: S347WMO6M4
• 维基百科标题: Beta-Sitosterol

理论计算性质

• Acid pKa: 18.20429
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 7.8444767
• LogD (pH = 7.4): 7.8444767
• Log P: 7.8444767
• 摩尔折射率: 129.7661 cm^3
• 极化性: 51.670784 Å^3
• 极化表面积: 20.23 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: chloroform: soluble20 mg/mL, clear, colorless
• 外观: Powder
• 熔点: 136-140 °C(lit.); 136–140 °C
• 比旋光度: [α]25/D -37°, c = 2 in chloroform

安全信息

• 保存条件: -20°C
• RTECS编号: WJ2600000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1888
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22-38-40-48/20/22
• 安全公开号: 36/37
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H315-H351-H373
• GHS警示性声明: P281
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1888 6.1/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥40%; ≥70%; ≥90% (GC); ≥95%; ≥97%; ≥97.0% (GC); 40%
• 浓度: 100 μg/mL in chloroform
• 级别: analytical standard
• 成盐信息: Free Base
• 包装: ampule of 1 mL
• 杂质: campesterol and β-sitostanol, residual
• 生物来源: from soybean; synthetic
• Empirical Formula (Hill Notation): C29H50O

详细说明

Selleck Chemicals - S2273

Research Area: Cardiovascular Disease
Biological Activity:
β-sitosterol reduces blood levels of cholesterol, and is sometimes used in treating hypercholesterolemia. β-Sitosterol inhibits cholesterol absorption in the intestine. When the sterol is absorbed in the intestine, it is transported by lipoproteins and incorporated into the cellular membrane. Phytosterols and phytostanols both inhibit the uptake of dietary and biliary cholesterol, decreasing the levels of LDL and serum total cholesterol. [1][2]

Sigma Aldrich - S9889

Biochem/physiol Actions
Plant derived estrogen
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S9889.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 85451

包装
100 g in poly bottle

Sigma Aldrich - S1270

Biochem/physiol Actions
A phytosterol with structure very similar to cholesterol that exhibits estrogenic activity. Inhibits proliferation of human leukemia cells, with G2/M arrest, endoreduplication, and polymerization of α-tubulin and microtubules.1

Sigma Aldrich - S5753

Quality
实习用经 13C-NMR 检测证实还含有菜油甾醇和二氢芜莆甾醇。1,2

参考文献

• Matsuoka K et al. Chem Phys Lipids. 2008 Aug;154(2):87-93.