20(S)-Hydroxycholesterol

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Category	Natural Sterols
Catalog NO.	BPG-3294
Product Name	20(S)-Hydroxycholesterol
CAS	516-72-3
Molecular Formula	C27H46O2
Molecular Weight	402.65

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Product Information
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Product Information

Description	20(S)-Hydroxycholesterol is an allosteric activator of the Hedgehog signaling pathway Smoothened (Smo) oncoprotein. 20(S)-Hydroxycholesterol induces Smo accumulation in primary cilia, and also exhibits osteogenic activity and activates the liver X receptor (LXR).
Synonyms	20-hydroxycholesterol; 20alpha-Hydroxycholesterol; (20S)-20-Hydroxycholesterol; cholest-5-en-3beta,20-diol; 20S-Cholest-5-ene-3beta,20-diol; 20α-hydroxycholesterol
IUPAC Name	(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-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)CCCC(C)(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
InChI	InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChIKey	MCKLJFJEQRYRQT-APGJSSKUSA-N
Melting Point	125-132°C
Purity	>99%
Solubility	Soluble in Chloroform and Methanol
Appearance	Powder
Shelf Life	3 months
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. Zhang Z, Yomo D, Gradinaru C. Choosing the right fluorophore for single-molecule fluorescence studies in a lipid environment. Biochim Biophys Acta Biomembr. 2017 Jul;1859(7):1242-1253. doi: 10.1016/j.bbamem.2017.04.001. Epub 2017 Apr 6. PMID: 28392350. PubMed ID: 28392350.

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