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22-alpha-Hydroxy Cholesterol

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Category	Glycosylated Sterols
Catalog NO.	BPG-3283
Product Name	22-alpha-Hydroxy Cholesterol
CAS	17954-98-2
Molecular Formula	C27H46O2
Molecular Weight	402.67

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Description	22α-Hydroxy Cholesterol is the 22R-metabolite of Cholesterol. 22-Hydroxycholesterol inhibits chemokine receptor activity.
Synonyms	(3β,22R)-Cholest-5-ene-3,22-diol; (20S,22R)-Cholest-5-ene-3β,22-diol; (22R)-22-Hydroxycholesterol; (22R)-Cholest-5-ene-3β,22-diol; (22R)-Hydroxycholesterol; 22α-Hydroxycholesterol; Cholest-5-ene-3β,22(R)-diol; Narthesterol
IUPAC Name	(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES	CC(C)CCC(C(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
InChI	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
InChIKey	RZPAXNJLEKLXNO-GFKLAVDKSA-N
Boiling Point	513.1°C at 760 mmHg
Melting Point	184-185°C
Purity	> 95%
Density	1.03 g/cm3
Appearance	Crystalline 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. Hassani-Nezhad-Gashti F, Salonurmi T, Hautajärvi H, Rysä J, Hakkola J, Hukkanen J. Pregnane X Receptor Activator Rifampin Increases Blood Pressure and Stimulates Plasma Renin Activity. Clin Pharmacol Ther. 2020 Apr 28. doi: 10.1002/cpt.1871. Epub ahead of print. PMID: 32344455. PubMed ID: 32344455.
2. 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.
3. Hutchinson SA, Lianto P, Roberg-Larsen H, Battaglia S, Hughes TA, Thorne JL. ER-Negative Breast Cancer Is Highly Responsive to Cholesterol Metabolite Signalling. Nutrients. 2019 Nov 1;11(11). pii: E2618. doi: 10.3390/nu11112618. PubMed ID: 31683867.
4. Solheim S, Hutchinson SA, Lundanes E, Wilson SR, Thorne JL, Roberg-Larsen H. Fast liquid chromatography-mass spectrometry reveals side chain oxysterol heterogeneity in breast cancer tumour samples. J Steroid Biochem Mol Biol. 2019 Feb 16. pii: S0960-0760(18)30754-4. doi: 10.1016/j.jsbmb.2019.02.004. [Epub ahead of print]...PubMed ID: 30779932.
5. Becares N, Gage MC, Voisin M, Shrestha E, Martin-Gutierrez L, Liang N, Louie R, Pourcet B, Pello OM, Luong TV, Goñi S, Pichardo-Almarza C, Røberg-Larsen H, Diaz-Zuccarini V, Steffensen KR, O'Brien A, Garabedian MJ, Rombouts K, Treuter E, Pineda-Torra I. Impaired LXRα Phosphorylation Attenuates Progression of Fatty Liver Disease. Cell Rep. 2019 Jan 22;26(4):984-995.e6. doi: 10.1016/j.celrep.2018.12.094. PubMed ID: 30673619.

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