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22-alpha-Hydroxy Cholesterol

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