24-Hydroxycholesterol

For research use only. Not for therapeutic Use.

  • CAT Number: I013435
  • CAS Number: 30271-38-6
  • Molecular Formula: C27H46O2
  • Molecular Weight: 402.65
  • Purity: ≥95%
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24-Hydroxycholesterol is a natural sterol, which serves as a positive allosteric modulator of N-Methyl-d-Aspartate (NMDA) receptorsR, and a potent activator of the transcription factors LXR.
24S-hydroxycholesterol oxysterol-generating enzyme Cyp46a1 is overexpressed during the angiogenic switch in rat insulin promoter 1-T-antigen 2 (RIP1-Tag2) pNET formation[1].
Hypoxia inducible factor-1a (HIF-1α) controls the overexpression of the enzyme Cyp46a1, which generates the oxysterol 24-hydroxycholesterol in a pancreatic neuroendocrine tumor (pNET) model commonly used to study neoangiogenesis. The activation of the HIF-1α-24S-HC axis ultimately leads to the induction of the angiogenic switch through the positioning of proangiogenic neutrophils in proximity to Cyp46a1+ islets[1]. 24-hydroxycholesterol levels are increased at 2-4 months in the untreated 5XFAD mouse brain and then became similar to those in the B6SJL mouse brain[2].


Catalog Number I013435
CAS Number 30271-38-6
Synonyms

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-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

Molecular Formula C27H46O2
Purity ≥95%
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-GHMQSXNDSA-N
SMILES CC(C)C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
Reference

[1]. Soncini M, et al. 24-Hydroxycholesterol participates in pancreatic neuroendocrine tumor development. Proc Natl Acad Sci U S A. 2016 Oct 11;113(41):E6219-E6227. Epub 2016 Sep 26.
 [Content Brief]

[2]. Mast N, et al. Cholesterol-metabolizing enzyme cytochrome P450 46A1 as a pharmacologic target for Alzheimer’s disease. Neuropharmacology. 2017 Sep 1;123:465-476.
 [Content Brief]

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