(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 ID: 53623
• Molecular Formular: C27H46O
• Molecular Mass: 386.65354
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Systematic name: 2,15-dimethyl-14-(1,5-dimethylhexyl)tetracyclo[8.7.0.0^2,7.0^11,15]heptacos-7-en-5-ol
• IUPAC Traditional name: cholesterol
• Synonyms: 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; 胆固醇素; 胆甾-5-烯-3β-醇; 胆甾醇; 胆固醇; 合成胆固醇

Database IDs

• CAS Number: 57-88-5
• EC Number: 200-353-2
• MDL Number: MFCD00003646
• Beilstein Number: 1915888
• Merck Index: 142201
• PubChem SID: 24892601; 24892335; 162058386; 24893094; 24852491; 24848759; 24856220; 24892388; 24899653; 24892329; 24893064
• PubChem CID: 5997
• CHEBI ID: 16113
• CHEMBL: 112570
• Chemspider ID: 5775
• KEGG ID: D00040
• Unique Ingredient Identifier: 97C5T2UQ7J
• Wikipedia Title: Cholesterol

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.112889
• LogD (pH = 7.4): 7.112889
• Log P: 7.112889
• Molar Refractivity: 120.6165 cm^3
• Polarizability: 47.977962 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 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
• Apperance: aqueous solution; powder; white crystalline powder; white powder; White Solid
• Melting Point: 137-144°C; 147-149 °C(lit.); 147-150 °C; 147-150°C; 148–150 °C
• Boiling Point: 360 °C (decomposes); 360 °C(lit.); 360°C
• Flash Point: 209.3 ±12.4°C
• Density: 1.052 g/cm^3; 1.067; 1.067 g/mL at 25 °C(lit.)
• Optical Rotation: [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)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• RTECS: FZ8400000
• UN Number: 1170
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 3
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1170 3/PG 3
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: Others
• Gene Information: human ... POLA1(5422), TOP2A(7153)rat ... Ar(24208), Polb(29240)

Product Information

• Purity: ≥92.5% (GC); ≥95% (GC); ≥95.0% (GC); ≥98%; ≥99%; ≥99.0%; 94%; 95%
• Concentration: 500 ×
• Grade: cGMP; Ph Eur; Sigma Grade
• Salt Data: Free Base
• Suitability: insect cell culture tested; suitable for cell culture
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: Ash, free
• Biological Source: from lanolin; from porcine liver; from sheep wool; synthetic
• Sterility: sterile-filtered
• Loss on Drying: ≤0.3% loss on drying, 60 °C, 4 h (vacuum)
• Type: Grade I
• Quality Level: GMP
• Quality: meets analytical specification of NF
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C27H46O
• Classification: Genuine Natural Compounds

DETAILS

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
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

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
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

Sigma Aldrich - C75209

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.
Packaging
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
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - C1231

Biochem/physiol Actions
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.
Preparation Note
Synthesized from material of non-animal origin
Legal Information
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.
Legal Information
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
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

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

REFERENCES

• 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)