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24(S)-Hydroxycholesterol

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Category	Natural Sterols
Catalog NO.	BPG-3290
Product Name	24(S)-Hydroxycholesterol
CAS	474-73-7
Molecular Formula	C27H46O2
Molecular Weight	402.65

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Product Information

Description	(3β,24S)-Cholest-5-ene-3,24-diol is used as a biomarker in the analysis of disease.
Synonyms	Cerebrosterol; Cholest-5-ene-3,24-diol; 24S-hydroxycholesterol; cholest-5-en-3beta,24S-diol; (24S)-cholest-5-ene-3beta,24-diol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-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)C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
InChI	InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(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-/m1/s1
InChIKey	IOWMKBFJCNLRTC-XWXSNNQWSA-N
Boiling Point	513.1°C at 760 mmHg
Melting Point	177-180°C
Purity	> 95%
Density	1.0 g/cm3
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. Rossin D, Dias IHK, Solej M, Milic I, Pitt AR, Iaia N, Scoppapietra L, Devitt A, Nano M, Degiuli M, Volante M, Caccia C, Leoni V, Griffiths HR, Spickett CM, Poli G, Biasi F. Increased production of 27-hydroxycholesterol in human colorectal cancer advanced stage: Possible contribution to cancer cell survival and infiltration. Free Radic Biol Med. 2019 Mar 23;136:35-44. doi: 10.1016/j.freeradbiomed.2019.03.020. [Epub ahead of print]...PubMed ID: 30910555.
2. 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.
3. Kakiyama G, Marques D, Takei H, Nittono H, Erickson S, Fuchs M, Rodriguez-Agudo D, Gil G, Hylemon PB, Zhou H, Bajaj JS, Pandak WM. Mitochondrial oxysterol biosynthetic pathway gives evidence for CYP7B1 as controller of regulatory oxysterols. J Steroid Biochem Mol Biol. 2019 Jan 30;189:36-47. doi: 10.1016/j.jsbmb.2019.01.011. [Epub ahead of print]...PubMed ID: 30710743.

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