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H9384

Sigma-Aldrich

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:
17954-98-2
Molecular Weight:
402.65
MDL number:
MFCD00070042
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
24895852
NACRES:
NA.77

Quality Level

200

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

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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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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Lourdes Cruz-Garcia et al.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology, 160(2), 125-136 (2011-06-04)
The liver X receptor (LXR) has recently been described in salmonids. In mammals, this receptor is already known as a transcriptional factor that regulates diverse aspects of cholesterol, fatty acid and carbohydrate metabolism in various tissues, including muscle. Here we
Cynthia Hong et al.
Journal of lipid research, 52(3), 531-539 (2010-12-29)
Ligand activation of liver X receptors (LXRs) has been shown to impact both lipid metabolism and inflammation. One complicating factor in studies utilizing synthetic LXR agonists is the potential for pharmacologic and receptor-independent effects. Here, we describe an LXR gain-of-function
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
V Papadopoulos et al.
Journal of neuroendocrinology, 24(1), 93-101 (2011-06-01)
The overall ability of the brain to synthesise neuroactive steroids led us to the identification of compounds that would reproduce aspects of neurosteroid pharmacology. The rate-determining step in neurosteroid biosynthesis is the import of the substrate cholesterol into the mitochondria
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