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24(S)-Hydroxycholesterol

Names

[ CAS No. ]:
474-73-7

[ Name ]:
24(S)-Hydroxycholesterol

[Synonym ]:
24S-hydroxycholesterol
Cholest-5-ene-3,24-diol
cholest-5-en-3beta,24S-diol
Cholest-5-ene-3,24-diol, (3β,24S)-
cholest-5-ene-3b,24a-diol
(3b,24S)-Cholest-5-ene-3,24-diol
24(S)-hydroxycholesterol
(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
(3β,24S)-Cholest-5-ene-3,24-diol
24S-Cholest-5-ene-3b,24-diol
24S-OHC
Cerebrosterol
24-hydroxycholesterol
24S-Hydroxy-cholesterol

Biological Activity

[Description]:

24(S)-Hydroxycholesterol (24S-OHC), the major brain cholesterol metabolite, plays an important role to maintain homeostasis of cholesterol in the brain. 24(S)-Hydroxycholesterol (24S-OHC) is one of the most efficient endogenous LXR agonist known and is present in the brain and in the circulation at relatively high levels. 24(S)-Hydroxycholesterol (24S-OHC) is a very potent, direct, and selective positive allosteric modulator of NMDARs with a mechanism that does not overlapthat of other allosteric modulators[1][2][3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR
Signaling Pathways >> Metabolic Enzyme/Protease >> LXR
Research Areas >> Metabolic Disease
Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[Target]

Human Endogenous Metabolite


[References]

[1]. Yuki Kimura, et al. Tocopherol suppresses 24(S)-hydroxycholesterol-induced cell death via inhibition of CaMKII phosphorylation. Biochimie. 2018 Oct;153:203-209.

[2]. M Shafaati, et al. Enhanced production of 24S-hydroxycholesterol is not sufficient to drive liver X receptor target genes in vivo. J Intern Med. 2011 Oct;270(4):377-87.

[3]. Steven M Paul, et al. The major brain cholesterol metabolite 24(S)-hydroxycholesterol is a potent allosteric modulator of N-methyl-D-aspartate receptors. J Neurosci. 2013 Oct 30;33(44):17290-300.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
513.1±23.0 °C at 760 mmHg

[ Melting Point ]:
174-176°C (lit.)

[ Molecular Formula ]:
C27H46O2

[ Molecular Weight ]:
402.653

[ Flash Point ]:
213.5±17.2 °C

[ Exact Mass ]:
402.349792

[ PSA ]:
40.46000

[ LogP ]:
7.66

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
20°C


Related Compounds