14606

Cholesterol

tested according to Ph. Eur.

• Synonym(s): Cholesterolum, 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: 41141804
• PubChem Substance ID: 329750548
• NACRES: NA.21

Properties

• agency: USP/NF; tested according to Ph. Eur.
• Quality Level: 100
• form: powder
• bp: 360 °C (lit.)
• mp: 147-149 °C (lit.)
• solubility: chloroform: soluble 1 gm in 4.5 ml; diethyl ether: soluble 1 gm in 2.8 ml; pyridine: soluble 1 gm in 1.5 ml; H₂O: insoluble; acetone: soluble; alcohol: slightly soluble; alcohol: very soluble (Hot); benzene: soluble; dioxane: soluble; ethyl acetate: soluble; hexane: soluble; oil: soluble; petroleum ether: soluble
• density: 1.067 g/mL at 25 °C (lit.)
• application(s): pharmaceutical (small molecule)
• storage temp.: 2-8°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 for preparing ISCOMS containing ovalbumin (OVA) for studying whether the incorporation of the protein antigen ovalbumin (OVA) in lipophilic immune-stimulating complexes (ISCOMS) induces very strong primary immune responses. It was incorporated in animal feed to study the effect of cholesterol-rich diet.

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.

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)