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24(R/S),25-epoxycholesterol

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Category	Oxysterols
Catalog NO.	BPG-3300
Product Name	24(R/S),25-epoxycholesterol
CAS	72542-49-5
Molecular Formula	C27H44O2
Molecular Weight	400.64

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Description	24(R/S),25-epoxycholesterol is a side chain substituted cholesterol. It has been used as a liver X receptor ligand in breast cancer cell lines. The level of 24(R/S),25-epoxycholesterol is elevated in gastric carcinoma and may also inhibit gastric tumor invasion. 24(R/S),25-epoxycholesterol regulates gastric epithelial function and also may modulate the phosphatidylinositol 3-kinase - protein kinase B (PI3K/AKT) signaling.
Synonyms	24(R/S),25-EC
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2R)-3,3-dimethyloxiran-2-yl]butan-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(CCC1C(O1)(C)C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C
InChI	InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24-,26+,27-/m1/s1
InChIKey	OSENKJZWYQXHBN-PJXSLZQESA-N
Purity	>99%
Appearance	Powder
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	400.334
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 80.94%, H 11.07%, O 7.99%

References

1. Hutchinson SA, Lianto P, Moore JB, Hughes TA, Thorne JL. Phytosterols Inhibit Side-Chain Oxysterol Mediated Activation of LXR in Breast Cancer Cells. Int J Mol Sci. 2019 Jul 2;20(13). pii: E3241. doi: 10.3390/ijms20133241. PubMed ID: 31269628.

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