24-Hydroxycholesterol

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.

Product information

CAS Number: 30271-38-6

Molecular Weight: 402.65

Formula: C27H46O2

Chemical Name: (1R,3aS,3bS,7S,9aR,9bS,11aR)-3a,3b,9b-trihydrogenio-1-[(2R)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

Smiles: CC(C)C(O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChiKey: IOWMKBFJCNLRTC-GHMQSXNDSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

24S-hydroxycholesterol oxysterol-generating enzyme Cyp46a1 is overexpressed during the angiogenic switch in rat insulin promoter 1-T-antigen 2 (RIP1-Tag2) pNET formation.

In Vivo:

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. 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.

References:

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.
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.

Products are for research use only. Not for human use.