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700075P

Avanti

8(9)-dehydrocholesterol

Avanti Polar Lipids 700075P, powder

Synonym(s):
cholesta-5,8(9)-dien-3β-ol
Empirical Formula (Hill Notation):
C27H44O
CAS Number:
Molecular Weight:
384.64
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700075P-1mg)

manufacturer/tradename

Avanti Polar Lipids 700075P

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)

Storage Class Code

13 - Non Combustible Solids

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

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

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