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About This Item
Empirical Formula (Hill Notation):
C27H44O
CAS Number:
Molecular Weight:
384.64
NACRES:
NA.25
UNSPSC Code:
12352211
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (700075P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
shipped in
dry ice
storage temp.
−70°C
SMILES string
C[C@]1(CC2)C(CCC1C(CCCC(C)C)C)C3=C2[C@](CC[C@H](O)C4)(C)C4=CC3
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/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1
InChI key
VUKORTMHZDZZFR-BXAZICILSA-N
General description
8(9)-dehydrocholesterol is an isomer of 7-dehydrocholesterol and non-polar oxysterol metabolite. It is oxidized to Δ8 analog by mitochondrial enzymes.
Application
8(9)-dehydrocholesterol has been used as a component of sterol standard in liquid chromatography–mass spectrometry (LC-MS) for quantification of lipids from cultured cells.
Biochem/physiol Actions
8(9)-dehydrocholesterol (8-DHC) elevated levels are toxic to cells and is implicated in Smith-Lemli-Opitz syndrome (SLOS). 8-DHC profiling helps in understanding SLOS phenotype.
Packaging
5 mL Amber Glass Screw Cap Vial (700075P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
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William J Griffiths et al.
The Journal of steroid biochemistry and molecular biology, 169, 77-87 (2016-03-16)
Smith-Lemli-Opitz syndrome (SLOS) is a severe autosomal recessive disorder resulting from defects in the cholesterol synthesising enzyme 7-dehydrocholesterol reductase (Δ7-sterol reductase, DHCR7, EC 1.3.1.21) leading to a build-up of the cholesterol precursor 7-dehydrocholesterol (7-DHC) in tissues and blood plasma. Although
Josi Herron et al.
Current protocols in toxicology, 78(1), e65-e65 (2018-10-16)
Cholesterol and cholesterol-derived oxysterols are critical for embryonic development, synapse formation and function, and myelination, among other biological functions. Indeed, alterations in levels of cholesterol, sterol precursors, and oxysterols result in a variety of developmental disorders, emphasizing the importance of
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 700075P-1MG | 04061835383535 |