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Merck
CN

700075P

Avanti

8(9)-dehydrocholesterol

Avanti Polar Lipids

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别名:
cholesta-5,8(9)-dien-3β-ol
经验公式(希尔记法):
C27H44O
CAS号:
分子量:
384.64
UNSPSC代码:
12352211
NACRES:
NA.25

检测方案

>99% (TLC)

形式

powder

包装

pkg of 1 × 1 mg (700075P-1mg)

制造商/商品名称

Avanti Polar Lipids

运输

dry ice

储存温度

−70°C

SMILES字符串

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

一般描述

8(9)-dehydrocholesterol is an isomer of 7-dehydrocholesterol and non-polar oxysterol metabolite. It is oxidized to Δ8 analog by mitochondrial enzymes.

应用

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.

生化/生理作用

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.

包装

5 mL Amber Glass Screw Cap Vial (700075P-1mg)

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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

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