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14606 Sigma-Aldrich

Cholesterol

tested according to Ph Eur

Synonym: 3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol, Cholesterolum

  • CAS Number 57-88-5

  • Empirical Formula (Hill Notation) C27H46O

  • Molecular Weight 386.65

  •  Beilstein/REAXYS Number 1915888

  •  EC Number 200-353-2

  •  MDL number MFCD00003646

  •  PubChem Substance ID 329750548

  •  NACRES NA.21

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Properties

Related Categories Analytical/Chromatography, Asymmetric Synthesis, Biochemicals and Reagents, Chemical Synthesis, Chiral Building Blocks,
Agency/Method   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.)
Featured Industry   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 & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
FZ8400000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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