Desmosterol
Chemical compound / From Wikipedia, the free encyclopedia
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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.[1] Structurally, desmosterol has a similar backbone to cholesterol, with the exception of an additional double bond in the structure of desmosterol.
Names | |
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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 | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.005.671 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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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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.[2] Desmosterol is accumulated in desmosterolosis and undergoes reduction with the catalyst 24-dehydrocholesterol reductase to form cholesterol.[3]
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).[4]