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Merck
CN

700061P

Avanti

24(S)-hydroxycholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

5-cholestene-3β,24-diol; 24-hydroxycholest-5-en-3-ol

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
474-73-7
Molecular Weight:
402.65
MDL number:
MFCD03695560
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

24(S)-hydroxycholesterol, Avanti Research™ - A Croda Brand

SMILES string

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CC[C@H](O)C(C)C)C)(CC3)C)CC=C2C1)C

InChI

1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

InChI key

IOWMKBFJCNLRTC-XWXSNNQWSA-N

description

cholest-5-ene-3β,24(S)-diol

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700061P-1mg)
pkg of 1 × 5 mg (700061P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

Application

24(S)-hydroxycholesterol has been used as an internal standard:
  • in ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS)
  • in liquid chromatography with tandem mass spectrometry (LC-MS/MS) for the quantification of 27-hydroxycholesterol from colorectal tumor samples
  • for quantification of human plasma sterols by liquid chromatography with tandem mass spectrometry (LC MS/MS)

Biochem/physiol Actions

24(S)-hydroxycholesterol (24HC) elevated levels are reported in liver inflammation and fibrosis. It is a N-methyl-D-aspartate receptor (NMDAR) modulator. The levels of 24HC are potential indicators of brain development as well as pathology including Alzheimer′s disease (AD) and multiple sclerosis. Polymorphism in the cholesterol 24-hydroxylase (CYP46A1) gene leads to elevated 24HC levels and toxicity. 24HC is a mediator of apoptosis and necroptosis. Elevated levels of 24HC are reported in liver inflammation and fibrosis.

General description

24(S)-hydroxycholesterol (24HC) is synthesized from cholesterol in brain dendrites by the action of enzyme cholesterol 24-hydroxylase (CYP46A1). It is catabolized to bile acids in the liver.

Packaging

5 mL Amber Glass Screw Cap Vial (700061P-1mg)
5 mL Amber Glass Screw Cap Vial (700061P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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24S-hydroxycholesterol and 25-hydroxycholesterol differentially impact hippocampal neuronal survival following oxygen-glucose deprivation
Sun MY, et al.
Testing, 12(3) (2017)
Diverse functions of 24 (S)-hydroxycholesterol in the brain
Noguchi N, et al.
Biochemical and Biophysical Research Communications, 446(3), 692-696 (2014)
Increased production of 27-hydroxycholesterol in human colorectal cancer advanced stage: Possible contribution to cancer cell survival and infiltration
Rossin D, et al.
Free Radical Biology & Medicine, 136, 35-44 (2019)
Quantitative detection of free 24S-hydroxycholesterol, and 27-hydroxycholesterol from human serum
Bandaru VVR and Haughey NJ
BMC Neuroscience, 15(1), 137-137 (2014)
A validated liquid chromatography-tandem mass spectrometry method for the quantitative determination of 4beta-hydroxycholesterol in human plasma
van de Merbel NC, et al.
Journal of Pharmaceutical and Biomedical Analysis, 55(5), 1089-1095 (2011)
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