The solubility of this material is tested in Chloroform at 20 mg/mL. Other solvents include ethanol, DMSO, and dimethylformamide at a lower rate. The solution stability has not been investigated. However, other sources report that solutions stored in solvent at -20°C to -80°C are stable for up to 6 months.
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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5 MG
€407.00
About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
MDL number:
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.77
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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
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Related Categories
Application
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.[4] 22(R)-Hydroxycholesterol acts as the ligand of liver X receptors that act as sensors of sterol concentration and regulates the fatty acid metabolism.[5]
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
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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
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
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
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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The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.
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Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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What is product H9384, 22(R)-Hydroxycholesterol, soluble in?
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Product H9384, 22(R)-Hydroxycholesterol, is reported to be soluble in chloroform (20mg/ml), absolute ethanol (20mg/ml), DMSO (0.1mg/ml) and dimethylformamide (2mg/ml). Sigma-Aldrich tests solubility of this compound in chloroform at a concentration of 20mg/ml.
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