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14606

Cholesterol

tested according to Ph. Eur.

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H46O
CAS Number:
57-88-5
Molecular Weight:
386.65
UNSPSC Code:
41141804
NACRES:
NA.21
PubChem Substance ID:
329750548
EC Number:
200-353-2
Beilstein/REAXYS Number:
1915888
MDL number:
MFCD00003646
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Quality Level

100

agency

tested according to Ph. Eur.

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)

research use (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)

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

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

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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