(3β,24S)-Cholest-5-ene-3,24-diol

• CAT Number: R018751
• CAS Number: 474-73-7
• Molecular Formula: C27H46O2
• Molecular Weight: 402.663
• Purity: ≥95%
• Synonyms: Cholest-5-ene-3β,24-diol; (24S)-24-Hydroxycholesterol; 24(S)-Hydroxycholesterol; 24-Hydroxycholesterol; 24S-Cholest-5-ene-3β,24-diol; Cerebrosterin; Cerebrosterol; Cholest-5-ene-3β,24β-diol
• Target: Neuronal Signaling
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• 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
• 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
• SMILES: CC(C)C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O

(3β,24S)-Cholest-5-ene-3,24-diol (CAS 474-73-7) is a side-<wbr style="box-sizing: border-box; font-family: Lato, "Lucida Grande", "Lucida Sans Unicode", "Lucida Sans", Geneva, Verdana, sans-serif; font-size: 16px;" />chain substituted oxysterol that has important roles in cholesterol homeostasis. It is generated by the action of CYP46 on cholesterol in the brain and diffuses across the blood-<wbr style="box-sizing: border-box; font-family: Lato, "Lucida Grande", "Lucida Sans Unicode", "Lucida Sans", Geneva, Verdana, sans-serif; font-size: 16px;" />brain barrier to the systemic circulation where it can modulate cell signaling, be used for further sterol biosynthesis, or be metabolized in the liver. It potently activates LXRα and LXRβ nuclear receptors (EC50 = 4 and 3 μM, respectively), causing upregulation of cholesterol-<wbr style="box-sizing: border-box; font-family: Lato, "Lucida Grande", "Lucida Sans Unicode", "Lucida Sans", Geneva, Verdana, sans-serif; font-size: 16px;" />lowering genes. In the brain, this oxysterol controls cholesterol processing to facilitate neurological repair during Alzheimer’s disease and other neuropathological conditions.

Reference

1.Vaya, Jacob, and Hyman M. Schipper. "Oxysterols, cholesterol homeostasis, and Alzheimer disease." Journal of neurochemistry 102.6 (2007): 1727-1737.
2.Janowski, Bethany A., et al. "Structural requirements of ligands for the oxysterol liver X receptors LXRα and LXRβ." Proceedings of the National Academy of Sciences 96.1 (1999): 266-271.
3.Geyeregger, R., M. Zeyda, and T. M. Stulnig. "Liver X receptors in cardiovascular and metabolic disease." Cellular and Molecular Life Sciences 63.5 (2006): 524-539.