Desmosterol - CAS 313-04-2

24-dehydro Cholesterol is an immediate precursor to cholesterol in the Bloch pathway of cholesterol biosynthesis. Structurally, it varies from cholesterol only by a single double bond at carbon 24 and has been used as cholesterol substitute in cellular membrane studies. During brain development, 24-dehydro cholesterol transiently accumulates, composing up to 30% of total brain sterol, where it is poised to rapidly enrich membrane sterols. However, defects in cholesterol synthesis can lead to a condition called, desmosterolosis, which results in an accumulation of excess 24-dehydro cholesterol. 24-dehydro Cholesterol has been reported to activate liver X receptor-target genes in both the liver of cholesterol-free mice and in cholesterol-starved macrophage foam cells in atherosclerotic lesions.

Catalog Number: R049349

CAS Number: 313-04-2

PubChem Substance ID:355160044

Molecular Formula: C27H44O

Molecular Weight:384.648

Purity: ≥95%

* For research use only. Not for human or veterinary use.

Synonym

Synonyms(3β)-Cholesta-5,24-dien-3-ol; Cholesta-5,24-dien-3β-ol; 24,25-Dehydrocholesterol; 24-Dehydrocholesterol; NSC 226126;

Property

Molecular Formula: C27H44O
Molecular Weight384.648
Purity≥95%
Storage-20°C

Computed Descriptor

IUPAC Name(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChIInChI=1S/C27H44O/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/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKeyAVSXSVCZWQODGV-DPAQBDIFSA-N
SMILESCC(CCC=C(C)C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C