Desmosterol

Desmosterol (Cholesta-5,24-dien-3β-ol) is a lipid present in the membrane of phytoplankton and an intermediate product in cholesterol synthesis in mammal cells. Structurally, desmosterol has a similar backbone to cholesterol, with the exception of an additional double bond in the structure of desmosterol.

Desmosterol
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 Y
    Key: AVSXSVCZWQODGV-DPAQBDIFSA-N Y
  • 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).
Y verify (what is YN ?)
Infobox references

The similarity can be seen biologically through the synthesis of cholesterol in the human body, as desmosterol is the immediate precursor to cholesterol in the Bloch pathway. Desmosterol is accumulated in desmosterolosis and undergoes reduction with the catalyst 24-dehydrocholesterol reductase to form cholesterol.

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

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