7β-Hydroxy Cholesterol

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Category	Glycosylated Sterols
Catalog NO.	BPG-3284
Product Name	7β-Hydroxy Cholesterol
CAS	566-27-8
Molecular Formula	C27H46O2
Molecular Weight	402.65

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Product Information

Description	7β-Hydroxy Cholesterol is a metabolite of Cholesterol. Increased levels of 7β-Hydroxycholesterol correlate with increased risk of cardiovascular diseases including atherosclerosis.
Synonyms	(3β,7β)-Cholest-5-ene-3,7-diol; Cholest-5-ene-3β,7β-diol; 5-Cholestene-3β,7β-diol; 7β-Hydroxycholest-5-en-3β-ol
IUPAC Name	(3S,7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C
InChI	InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1
InChIKey	OYXZMSRRJOYLLO-KGZHIOMZSA-N
Melting Point	165-167°C (lit.)
Purity	> 95%
Solubility	Soluble in Chloroform and Methanol
Appearance	White to Off-white Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	402.35
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 80.54%, H 11.51%, O 7.95%

References

1. Olżyńska A, Kulig W, Mikkolainen H, Czerniak T, Jurkiewicz P, Cwiklik L, Rog T, Hof M, Jungwirth P, Vattulainen I. Tail-Oxidized Cholesterol Enhances Membrane Permeability for Small Solutes. Langmuir. 2020 Aug 28. doi: 10.1021/acs.langmuir.0c01590. Epub ahead of print. PMID: 32804507. PubMed ID: 32804507.
2. Yalcinkaya M, Kerksiek A, Gebert K, Annema W, Sibler R, Radosavljevic S, Luetjohann D, Rohrer L, von Eckardstein A. HDL inhibits endoplasmic reticulum stress-induced apoptosis of pancreatic β-cells in vitro by activation of Smoothened. J Lipid Res. 2020 Jan 6:jlr.RA119000509. doi: 10.1194/jlr.RA119000509. Epub ahead of print. PMID: 31907205. PubMed ID: 31907205.
3. Wang C, Siriwardane DA, Jiang W, Mudalige T. Quantitative analysis of cholesterol oxidation products and desmosterol in parenteral liposomal pharmaceutical formulations. Int J Pharm. 2019 Oct 5;569:118576. doi: 10.1016/j.ijpharm.2019.118576. Epub 2019 Jul 27. PubMed ID: 31362094.
4. Rossin D, Barbosa-Pereira L, Iaia N, Testa G, Sottero B, Poli G, Zeppa G, Biasi F. A Dietary Mixture of Oxysterols Induces In Vitro Intestinal Inflammation through TLR2/4 Activation: The Protective Effect of Cocoa Bean Shells. Antioxidants (Basel). 2019 May 31;8(6). pii: E151. doi: 10.3390/antiox8060151. PubMed ID: 31151323.
5. Kunz S, Matysik S. A comprehensive method to determine sterol species in human faeces by GC-triple quadrupole MS. J Steroid Biochem Mol Biol. 2019 Mar 25;190:99-103. doi: 10.1016/j.jsbmb.2019.03.014. [Epub ahead of print]...PubMed ID: 30923016.

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