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7α-Hydroxy Cholesterol

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Category	Cholesteryl Esters
Catalog NO.	BPG-3282
Product Name	7α-Hydroxy Cholesterol
CAS	566-26-7
Molecular Formula	C27H46O2
Molecular Weight	402.65

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Description	7α-hydroxy Cholesterol is an oxysterol and a precursor in the biosynthesis of the bile acids cholic acid and chenodeoxycholic acid. 7α-Hydroxy Cholesterol is also a secondary metabolite of Cholesterol. 7α-hydroxy Cholesterol (40 µM) increases levels of the adhesion molecules ICAM-1, VCAM-1, and E-selectin in human umbilical vein endothelial cells (HUVECs).
Synonyms	cholest-5-ene-3β,7α-diol; 7alpha-hydroxy-cholesterol; 7-alpha-OHC
IUPAC Name	(3S,7S,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-RVOWOUOISA-N
Boiling Point	515.3°C at 760 mmHg
Melting Point	183-185°C
Purity	> 95%
Solubility	Soluble in Chloroform
Appearance	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. Abrams ME, Johnson KA, Perelman SS, Zhang LS, Endapally S, Mar KB, Thompson BM, McDonald JG, Schoggins JW, Radhakrishnan A, Alto NM. Oxysterols provide innate immunity to bacterial infection by mobilizing cell surface accessible cholesterol. Nat Microbiol. 2020 Apr 13. doi: 10.1038/s41564-020-0701-5. Epub ahead of print. PMID: 32284563. PubMed ID: 32284563.
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. 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.
4. Wnętrzak A, Chachaj-Brekiesz A, Janikowska-Sagan M, Dynarowicz-Latka P. Influence of 7α-hydroxycholesterol on sphingomyelin and sphingomyelin/phosphatidylcholine films - The Langmuir monolayer study complemented with theoretical calculations. Biochim Biophys Acta Biomembr. 2019 Apr 1;1861(4):861-870. doi: 10.1016/j.bbamem.2019.01.020. Epub 2019 Feb 1. PubMed ID: 30716293.
5. Wang X, Sun J, Zhao XE, Xu Y, Sun L, Zhu S, You J, Wang X. Stable isotope labeling derivatization coupled with magnetic dispersive solid phase extraction for the determination of hydroxyl-containing cholesterol and metabolites by in vivo microdialysis and ultra-high performance liquid chromatography tandem mass spectrometry. J Chromatogr A. 2019 Feb 14. pii: S0021-9673(19)30151-7. doi: 10.1016/j.chroma.2019.02.021. [Epub ahead of print]...PubMed ID: 30797576.

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