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

• ChemBase编号: 53623
• 分子式: C27H46O
• 平均质量: 386.65354
• 单一同位素质量: 386.35486609
• SMILES: [C@@]12([C@H]([C@H]3[C@@H]([C@@]4(C(=CC3)C[C@H](CC4)O)C)CC2)CC[C@@H]1[C@@H](CCCC(C)C)C)C
• Canonical SMILES: CC(CCC[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)C
• InChI: InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: HVYWMOMLDIMFJA-DPAQBDIFSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC系统名: 2,15-dimethyl-14-(1,5-dimethylhexyl)tetracyclo[8.7.0.0^2,7.0^11,15]heptacos-7-en-5-ol
• IUPAC传统名: cholesterol
• 别名: 胆固醇素; 胆甾-5-烯-3β-醇; 胆甾醇; 胆固醇; 合成胆固醇; Cholest-5-en-3-ol; Cholesterol solution; SyntheChol™ NS0 Supplement; Cholesterolum; (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; 3β-Hydroxy-5-cholestene; 5-Cholesten-3β-ol; (3β)-Cholest-5-en-3-ol; (-)-Cholesterol; 3β-Hydroxycholest-5-ene; 5:6-Cholesten-3β-ol; Cholest-5-en-3β-ol; Cholesterin; Cholesteryl Αlcohol; Dythol; Lidinit; Lidinite; NSC 8798; Provitamin D; 5-Cholesten-3beta-ol; Cholesterol; (10R,13R)-10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; Cholesteril; Cholesteryl alcohol; Cholesterol; Synthetic cholesterol

登记号

• CAS号: 57-88-5
• EC号: 200-353-2
• MDL号: MFCD00003646
• Beilstein号: 1915888
• 默克索引号: 142201
• PubChem SID: 24892601; 24892335; 24856220; 162058386; 24893094; 24848759; 24892388; 24899653; 24892329; 24852491; 24893064
• PubChem CID: 5997
• CHEBI ID: 16113
• CHEMBL: 112570
• Chemspider ID: 5775
• KEGG ID: D00040
• 美国药典/FDA物质标识码: 97C5T2UQ7J
• 维基百科标题: Cholesterol

理论计算性质

• Acid pKa: 18.20429
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 7.112889
• LogD (pH = 7.4): 7.112889
• Log P: 7.112889
• 摩尔折射率: 120.6165 cm^3
• 极化性: 47.977962 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: 0.095 mg/L (30 °C) in water; Chloroform; Do you have solubility information on this product that you would like to share?; ethanol: soluble; H2O: soluble0.002 mg/mL; serum: soluble; soluble in acetone, benzene, chloroform, ethanol, ether, hexane, isopropyl myristate, methanol; Tween: soluble
• 外观: aqueous solution; powder; white crystalline powder; white powder; White Solid
• 熔点: 137-144°C; 147-149 °C(lit.); 147-150 °C; 147-150°C; 148–150 °C
• 沸点: 360 °C (decomposes); 360 °C(lit.); 360°C
• 闪点: 209.3 ±12.4°C
• 密度: 1.052 g/cm^3; 1.067; 1.067 g/mL at 25 °C(lit.)
• 比旋光度: [α]20/D -36±2°, c = 2% in dioxane; [α]20/D -38 to -34°, c = 2% in dioxane; [α]20/D -39°, c = 2 in chloroform; [α]20/D -40°, c = 2 in chloroform; -36 (c=2 in dioxane)

安全信息

• 保存条件: Refrigerator
• 保存注意事项: IRRITANT
• RTECS编号: FZ8400000
• 联合国危险货物编号: 1170
• 德国WGK号: 1; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3
• TSCA收录: false; 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1170 3/PG 3
• 保存温度: -20°C; 2-8°C

药理学性质

• 作用靶点: Others
• 相关基因信息: human ... POLA1(5422), TOP2A(7153)rat ... Ar(24208), Polb(29240)

产品相关信息

• 纯度: ≥92.5% (GC); ≥95% (GC); ≥95.0% (GC); ≥98%; ≥99%; ≥99.0%; 94%; 95%
• 浓度: 500 ×
• 级别: cGMP; Ph Eur; Sigma Grade
• 成盐信息: Free Base
• 适用性: insect cell culture tested; suitable for cell culture
• 燃烧残渣: ≤0.1% (as SO4)
• 杂质: Ash, free
• 生物来源: from lanolin; from porcine liver; from sheep wool; synthetic
• 无菌消毒: sterile-filtered
• 干燥失重: ≤0.3% loss on drying, 60 °C, 4 h (vacuum)
• 产品类型: Grade I
• 产品质量级别: GMP
• 品质说明: meets analytical specification of NF
• 药典: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C27H46O
• 分类: Genuine Natural Compounds

详细说明

Sigma Aldrich - C3292

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
Preparation Note
Precipitated from alcohol

Sigma Aldrich - 26740

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。

Sigma Aldrich - C3137

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
Linkage
Formerly Cat. No. CH-PL

Sigma Aldrich - 14606

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。

Sigma Aldrich - C75209

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
包装
25, 100, 500 g in poly bottle

Sigma Aldrich - C8503

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
Quality
Equivalent to USP/NF

Sigma Aldrich - 362794

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
包装
5, 25 g in glass bottle

Sigma Aldrich - C1231

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
Preparation Note
由非动物源物质合成
法律信息
SyntheChol is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - C3045

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。

Sigma Aldrich - C9913

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
Preparation Note
由非动物源物质合成
法律信息
SyntheChol is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - S5442

Features and Benefits
Synthetic, non-animal cholesterol solution that is designed as a supplement to our hybridoma media formulations to promote excellent cell growth and protein productivity for NS0 mouse myeloma and other cholesterol-dependent cell lines.
法律信息
SyntheChol is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - C2044

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。

Sigma Aldrich - 20808

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。

Sigma Aldrich - C8667

Biochem/physiol Actions
所有生物膜的主要成分；总脑脂质中含 ~25% 的胆固醇。
包装
1, 5, 25, 100 g in poly bottle
500 mg in poly bottle

Toronto Research Chemicals - C432501

Cholesterol is a major component of all biological membranes; ~25% of total brain lipid is Cholesterol. Cholesterol is the principal sterol of the higher animals. Cholesterol was found in all body tissues, especial in the brain, spinal cord, and in animal

参考文献

• Rosin, Z., et al.: Physiol. Chem., 124, 282 (1923)
• Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1923)
• Gemant, et al.: Life Sci., 1, 233 (1923)
• Johnson, K., et al.: 4, 457 (1923)