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24(R)-hydroxycholesterol

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Category	Natural Sterols
Catalog NO.	BPG-3291
Product Name	24(R)-hydroxycholesterol
CAS	27460-26-0
Molecular Formula	C27H46O2
Molecular Weight	402.65

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Description	24(S)-Hydroxy cholesterol is a side-chain substituted oxysterol that is generated from the action of CYP46 on cholesterol found in the brain and plays an important role in cholesterol homeostasis. 24(R)-hydroxy Cholesterol is a synthetic enantiomer of 24(S)-hydroxy cholesterol that activates LXRα and LXRβ nuclear receptors with slightly reduced potency.
Synonyms	(24R)-cholest-5-ene-3beta,24-diol; (3beta,24R)-Cholest-5-ene-3,24-diol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-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-RNCHBCSGSA-N
Boiling Point	513.1±23.0 °C at 760 mmHg
Melting Point	184-187°C
Purity	≥98%
Density	1.03±0.1 g/cm3
Solubility	Soluble in Chloroform (Slightly), Ethyl Acetate (Slightly)
Appearance	White to Off-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. 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.
2. Tajima N, Xiaoyan L, Taniguchi M, Kato N. 24S-hydroxycholesterol alters activity of large-conductance Ca2+-dependent K+ (slo1 BK) channel through intercalation into plasma membrane. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 May 25. pii: S1388-1981(19)30085-X. doi: 10.1016/j.bbalip.2019.05.010. [Epub ahead of print]...PubMed ID: 31136842.
3. 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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