Desmosterol
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Desmosterol
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CAS No:
313-04-2
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Formula:
C27H44O
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Chemical Name:
Desmosterol
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Synonyms:
Cholesta-5,24-dien-3-ol,(3β)-;Cholesta-5,24-dien-3β-ol;(3β)-Cholesta-5,24-dien-3-ol;24-Dehydrocholesterol;Desmosterol;24,25-Dehydrocholesterol;NSC 226126;OR 942 (Sterol)
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CAS No:
Description
Off-White Solid
Solid
Desmosterol is a cholestanoid that is cholesta-5,24-diene substituted by a beta-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol. It has a role as a human metabolite and a mouse metabolite. It is a 3beta-sterol, a cholestanoid, a C27-steroid and a 3beta-hydroxy-Delta(5)-steroid.|An intermediate in the synthesis of cholesterol.
Characteristics
20.2
9.54
Solid
1.0±0.1 g/cm3
121.5 °C
483.2±14.0 °C at 760 mmHg
209.2±12.4 °C
1.536
199.4 Ų [M+H-H2O]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|210.05 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
Desmosterol Use and Manufacturing
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.[Cayman Chemical] A metabolite of Cholesterol (C432501).
Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Computed Properties
Molecular Weight:384.6
XLogP3:8.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:384.339216023
Monoisotopic Mass:384.339216023
Topological Polar Surface Area:20.2
Heavy Atom Count:28
Complexity:641
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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