Cholesterol, water-permeable lipid

Key facts

CAS number

57-88-5

Purity

>98%

Molecular weight

386.7 Da

Molecular formula

C₂₇H₄₆O

PubChem

5997

Nature

Synthetic

Solubility

Soluble in chloroform, ether or pyridine

Insoluble in water

Biochemical name

Cholesterol

Biological description

Water-permeable lipid and major component of all biological membranes. Distributed in body tissues, especially the brain and spinal cord. Inhibits basal channel activity in the brain. Use as emulsifying agent and liposome preparations. Active in vivo and in vitro.

Canonical smiles

CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C

Isomeric smiles

C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C

InChi

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

InChiKey

HVYWMOMLDIMFJA-DPAQBDIFSA-N

IUPAC Name

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol