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H9384 Sigma-Aldrich

22(R)-Hydroxycholesterol

≥98%

Synonym: 22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol

  • CAS Number 17954-98-2

  • Empirical Formula (Hill Notation) C27H46O2

  • Molecular Weight 402.65

  •  MDL number MFCD00070042

  •  eCl@ss 39023139

  •  PubChem Substance ID 24895852

  •  NACRES NA.77

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Properties

Related Categories Biochemicals and Reagents, Cell Biology, Cholesterol and Derivatives, Lipids, Metabolic Pathways,
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

Description

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.

Packaging

1, 5 mg in glass bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H9384.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

How does the storage temperature relate to shipping conditions?
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. See Shipping and Storage for more information.
Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
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What is the Department of Transportation shipping information for this product?
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.
What is product H9384, 22(R)-Hydroxycholesterol, soluble in?
Product H9384, 22(R)-Hydroxycholesterol, is reported to besoluble 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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Protocols & Articles
Peer-Reviewed Papers
15

References

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