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25-hydroxycholesterol-3-sulfate

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Category	Glycosylated Sterols
Catalog NO.	BPG-3285
Product Name	25-hydroxycholesterol-3-sulfate
CAS	884905-07-1
Molecular Formula	C27H45NaO5S
Molecular Weight	504.698

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Product Information

Synonyms	25-hydroxycholesterol-3-sulfate (sodium salt)
IUPAC Name	[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-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-yl] hydrogen sulfate
Canonical SMILES	CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OS(=O)(=O)O)C)C
InChI	InChI=1S/C27H46O5S/c1-18(7-6-14-25(2,3)28)22-10-11-23-21-9-8-19-17-20(32-33(29,30)31)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28H,6-7,9-17H2,1-5H3,(H,29,30,31)/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChIKey	PIUZYOCNZPYXOA-ZHHJOTBYSA-N
Purity	>99%
Appearance	Powder
Shelf Life	1 Year
Storage	-20°C
Exact Mass	504.289
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 64.25%, H 8.99%, Na 4.56%, O 15.85%, S 6.35%

References

1. Beck KR, Inderbinen SG, Kanagaratnam S, Kratschmar DV, Jetten AM, Yamaguchi H, Odermatt A. 11β-Hydroxysteroid dehydrogenases control access of 7β,27-dihydroxycholesterol to retinoid-related orphan receptor γ. J Lipid Res. 2019 Sep;60(9):1535-1546. doi: 10.1194/jlr.M092908. Epub 2019 Jul 4. PMID: 31273032; PMCID: PMC6718442. PubMed ID: 31273032.
2. Xu L, Bai Q, Rodriguez-Agudo D, Hylemon PB, Heuman DM, Pandak WM, Ren S. Regulation of hepatocyte lipid metabolism and inflammatory response by 25-hydroxycholesterol and 25-hydroxycholesterol-3-sulfate. Lipids. 2010 Sep;45(9):821-32. doi: 10.1007/s11745-010-3451-y. Epub 2010 Aug 11. PMID: 20700770. PubMed ID: 20700770.
3. Ma Y, Xu L, Rodriguez-Agudo D, Li X, Heuman DM, Hylemon PB, Pandak WM, Ren S. 25-Hydroxycholesterol-3-sulfate regulates macrophage lipid metabolism via the LXR/SREBP-1 signaling pathway. Am J Physiol Endocrinol Metab. 2008 Dec;295(6):E1369-79. doi: 10.1152/ajpendo.90555.2008. Epub 2008 Oct 14. PMID: 18854425; PMCID: PMC2603552. PubMed ID: 18854425.
4. Ren S, Li X, Rodriguez-Agudo D, Gil G, Hylemon P, Pandak WM. Sulfated oxysterol, 25HC3S, is a potent regulator of lipid metabolism in human hepatocytes. Biochem Biophys Res Commun. 2007 Sep 7;360(4):802-8. doi: 10.1016/j.bbrc.2007.06.143. Epub 2007 Jul 6. PMID: 17624300; PMCID: PMC2728003. PubMed ID: 17624300.

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