Desmosterol

Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis.[1] 24-dehydrocholesterol reductase catalyses the reduction of desmosterol to cholesterol.[2] It is accumulated in desmosterolosis.

Desmosterol
Skeletal formula of desmosterol
Ball-and-stick model of the desmosterol molecule
Names
IUPAC name
Cholesta-5,24-dien-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.671
UNII
  • InChI=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 checkY
    Key: AVSXSVCZWQODGV-DPAQBDIFSA-N checkY
  • InChI=1/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
    Key: AVSXSVCZWQODGV-DPAQBDIFBV
  • O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CC\C=C(/C)C)C)[C@@]3(C)CC4
Properties
C27H44O
Molar mass 384.64 g/mol
Appearance White powder
Melting point 121.5 °C (250.7 °F; 394.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In 2014, it was named the Molecule of the Year 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (ISMCBBPR).[3]

See also

References
  1. Vainio, S.; Jansen, M.; Koivusalo, M.; Rog, T.; Karttunen, M.; Vattulainen, I.; Ikonen, E. (25 October 2005). "Significance of Sterol Structural Specificity: DESMOSTEROL CANNOT REPLACE CHOLESTEROL IN LIPID RAFTS". Journal of Biological Chemistry. 281 (1): 348–355. doi:10.1074/jbc.M509530200. PMID 16249181. Retrieved 30 June 2015.
  2. Keber, R.; Rozman, D.; Horvat, S. (23 October 2012). "Sterols in spermatogenesis and sperm maturation". The Journal of Lipid Research. 54 (1): 20–33. doi:10.1194/jlr.R032326. PMC 3520525. PMID 23093550. Retrieved 30 June 2015.
  3. "Announcing ISMCBBPR's Molecule of the Year 2012". Archived from the original on 2015-09-24. Retrieved 2014-02-22.


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