| Identification | Back Directory | [Name]
DESMOSTEROL | [CAS]
313-04-2 | [Synonyms]
Desmostero
DESMOSTEROL
24-DEHYDROCHOLESTEROL
Cholesterol impurity B
Cholesterol Impurity 12
Cholesta-5,24-dien-3-ol
desmosterol crystalline
5,24-Cholestadien-3β-ol
24,25-Didehydrocholesterol
5,24-CHOLESTADIEN-3BETA-OL
Cholesta-5,24-dien-3beta-ol
3-hydroxy-5,24-cholestadiene
Cholesta-5,24-dien-3-ol, (3β)-
3BETA-HYDROXY-5,24-CHOLESTADIENE
Cholesta-5,24-dien-3-ol, (3beta)-
Cholesterol EP Impurity B (Desmosterol)
3-HYDROXY-5,24-CHOLESTADIENE;DESMOSTEROL
24-Dehydrocholesterol, 3β-Hydroxy-5,24-cholestadiene, 5,24-Cholestadien-3β-ol
(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
(3S,8S,9S,10R,13R,14S,17R)-10,13-diMethyl-17-((R)-6-Methylhept-5-en-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | [EINECS(EC#)]
206-236-2 | [Molecular Formula]
C27H44O | [MDL Number]
MFCD00056432 | [MOL File]
313-04-2.mol | [Molecular Weight]
384.65 |
| Chemical Properties | Back Directory | [Melting point ]
121.5°, also reported as 119-119.5° | [alpha ]
D27 -41.0° (c = 1 in chloroform) | [Boiling point ]
483.2±14.0 °C(Predicted) | [density ]
1.00±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
15.03±0.70(Predicted) | [color ]
Wihte to Off-White | [InChIKey]
AVSXSVCZWQODGV-XFNGPGOHNA-N | [SMILES]
C[C@]12CC[C@]3([H])[C@]4(CC[C@H](O)CC4=CC[C@@]3([H])[C@]1([H])CC[C@]2([H])[C@H](C)CCC=C(C)C)C |&1:1,4,6,9,15,17,21,23,r| |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
Desmosterol has been used as a sterol to test its interaction with human protein Mincle and as an internal standard in ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). It may be used as in the preparation of lipid monolayers. | [Uses]
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] | [Uses]
A metabolite of Cholesterol (C432501). | [Definition]
ChEBI: 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. | [General Description]
Desmosterol lacks a double bond between C24 and C25 compared to cholesterol. It is present in the membrane of spermatozoa and astrocytes and is the major brain sterol. | [Biochem/physiol Actions]
Desmosterol is a precursor of cholesterol in the Bloch pathway and the enzyme 24-dehydrocholesterol reductase catalyzes this step. Desmosterol accumulates during impairment of 24-dehydrocholesterol reductase enzyme thereby leading to desmosterolosis. Desmosterol is a liver X receptor (LXR) agonist . It is a potential therapeutic target for treating the neurodegenerative disorder. Desmosterol regulates inflammatory signaling in macrophages. | [storage]
Store at -20°C |
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