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26740 Sigma-Aldrich

Cholesterol

from lanolin, ≥95.0% (GC)

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

  • 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

  •  eCl@ss 39023139

  •  PubChem Substance ID 57648186

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Properties

Related Categories Biochemicals and Reagents, Cholesterol and Derivatives, Lipids, Sterol Lipids
biological source   lanolin
assay   ≥95.0% (GC)
form   powder with small lumps
optical activity   [α]20/D −36±2°, c = 2% in dioxane
bp   360 °C (lit.)
mp   147-149 °C (lit.)
  147-150 °C
density   1.067 g/mL at 25 °C (lit.)
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 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.

Biochem/physiol Actions

Cholesterol is a lipid 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 
WGK Germany 
1
RTECS 
FZ8400000

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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