C8667

Cholesterol

Sigma Grade, ≥99%

• Synonym(s): 3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol
• Empirical Formula (Hill Notation): C₂₇H₄₆O
• CAS Number: 57-88-5
• Molecular Weight: 386.65
• Beilstein/REAXYS Number: 1915888
• EC Number: 200-353-2
• MDL number: MFCD00003646
• UNSPSC Code: 12352111
• eCl@ss: 39023139
• PubChem Substance ID: 24893094
• NACRES: NA.77

Properties

• biological source: sheep wool
• Quality Level: 200
• grade: Sigma Grade
• assay: ≥99%
• form: powder
• bp: 360 °C (lit.)
• mp: 147-149 °C (lit.)
• solubility: water: soluble 0.00003 g/L at 20 °C
• density: 1.067 g/mL at 25 °C (lit.)
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
• 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
• InChI key: HVYWMOMLDIMFJA-DPAQBDIFSA-N
• Gene Information: human ... POLA1(5422), TOP2A(7153) ; rat ... Ar(24208), Polb(29240)

Description

Application

Cholesterol was used to prepare immune-stimulating complexes to enhance cellular and humoral responses. It was incorporated in animal feed to study the effect of cholesterol-rich diet.

Standard for chromatography

Biochem/physiol Actions

Cholesterol is a lipid that makes up about 20-25% of the structural components of the cell membranes. It determines the fluidity and permeability of the membrane, making it permeable to water but not to ions and protons. Cholesterol also regulates the functions of the transporters and signaling proteins present on the plasma membrane. The major sites of cholesterol synthesis are small intestine and liver.

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

Preparation Note

Cholesterol monohydrate yields a clear, colorless to faint yellow solution in hot alcohol. It is also soluble in acetone, dioxane, ethyl acetate, benzene, petroleum ether, oils, fats, and in aqueous solutions of bile salts. Solutions should be protected from light.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)