H9384
22(R)-Hydroxycholesterol
≥98%
Synonym(s):
22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol
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About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Quality Level
assay
≥98%
form
powder
shipped in
ambient
storage temp.
room temp
SMILES string
[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)[C@H](O)CCC(C)C
InChI
1S/C27H46O2/c1-17(2)6-11-25(29)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+/m0/s1
InChI key
RZPAXNJLEKLXNO-GFKLAVDKSA-N
Application
Bovine aortic endothelial cells were treated with 22(R)-Hydroxycholesterol to study the effects on production of free radicals and in studies related to fatty acid metabolism.
Biochem/physiol Actions
22(R)-Hydroxycholesterol is an intermediate of the pregnenolone synthesis pathway from cholesterol. It reported has neuroprotective properties and protects the neurons against β-amyloid-induced cell death. 22(R)-Hydroxycholesterol acts as the ligand of liver X receptors that act as sensors of sterol concentration and regulates the fatty acid metabolism.
Preparation Note
22(R)-Hydroxycholesterol yield clear, colorless solution in chloroform.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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A Chawla et al.
Science (New York, N.Y.), 294(5548), 1866-1870 (2001-12-01)
Cholesterol, fatty acids, fat-soluble vitamins, and other lipids present in our diets are not only nutritionally important but serve as precursors for ligands that bind to receptors in the nucleus. To become biologically active, these lipids must first be absorbed
Zhi-Xing Yao et al.
Journal of neurochemistry, 83(5), 1110-1119 (2002-11-20)
22R-hydroxycholesterol, a steroid intermediate in the pathway of pregnenolone formation from cholesterol, was found at lower levels in Alzheimer's disease (AD) hippocampus and frontal cortex tissue specimens compared to age-matched controls. beta-Amyloid (Abeta) peptide has been shown to be neurotoxic
Jingsong Ou et al.
Circulation research, 97(11), 1190-1197 (2005-10-15)
Previously we showed L-4F, a novel apolipoprotein A-I (apoA-I) mimetic, improved vasodilation in 2 dissimilar models of vascular disease: hypercholesterolemic LDL receptor-null (Ldlr(-/-)) mice and transgenic sickle cell disease mice. Here we determine the mechanisms by which D-4F improves vasodilation
Global Trade Item Number
| SKU | GTIN |
|---|---|
| H9384-1MG | 04061833812440 |
| H9384-5MG | 04061833812457 |