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SML1648

24(S)-Hydroxycholesterol

Name: 24(S)-Hydroxycholesterol
Brand: SIGMA

≥98% (HPLC), cholesterol metabolite, powder

Synonym(s):

24S-Hydroxycholesterol, 5-Cholesten-3β,24(S)-diol, Cerebrosterin, Cerebrosterol, Cholest-5-ene-3β,24-diol

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₄₆O₂

CAS Number:

474-73-7

Molecular Weight:

402.65

UNSPSC Code:

12352211

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Product Name

24(S)-Hydroxycholesterol, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -45 to -52°, c = 1 in chloroform-d

storage condition

desiccated

color

white to beige

solubility

DMSO: 3 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CC[C@H](O)C(C)C)C)(CC3)C)CC=C2C1)C

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

InChI key

IOWMKBFJCNLRTC-XWXSNNQWSA-N

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Related Categories

Bioactive Small Molecules

Biochem/physiol Actions

24(S)-Hydroxycholesterol is the major brain metabolite formed from cholesterol in the brain and is important for brain cholesterol homeostasis in addition to being an an endogenous agonist of the nuclear liver X receptors (LXRs). Impairment of brain cholesterol metabolism has been associated with several neurodegenerative diseases, including multiple sclerosis, Alzheimer′s, and Huntington diseases. The exact role role of 24(S)-Hydroxycholesterol is unclear, and it may have differing effects depending on concentration. Low concentrations can protect neuronal cells against oxidative stress, while high concentrations induce necroptosis-like neuronal cell death. 24(S)-Hydroxycholesterol has also been found to be a potent allosteric modulator of N-methyl-d-aspartate receptors, potentiating NMDAR-mediated EPSCs in rat hippocampal neurons with an EC₅₀ of 1.2 μM.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000543498

0000402311

0000296341

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The major brain cholesterol metabolite 24(S)-hydroxycholesterol is a potent allosteric modulator of N-methyl-D-aspartate receptors.

Steven M Paul et al.

The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(44), 17290-17300 (2013-11-01)

N-methyl-D-aspartate receptors (NMDARs) are glutamate-gated ion channels that are critical to the regulation of excitatory synaptic function in the CNS. NMDARs govern experience-dependent synaptic plasticity and have been implicated in the pathophysiology of various neuropsychiatric disorders including the cognitive deficits

Mitochondrial oxysterol biosynthetic pathway gives evidence for CYP7B1 as controller of regulatory oxysterols.

Genta Kakiyama et al.

The Journal of steroid biochemistry and molecular biology, 189, 36-47 (2019-02-03)

The aim of this paper was to more completely study the mitochondrial CYP27A1 initiated acidic pathway of cholesterol metabolism. The mitochondrial CYP27A1 initiated pathway of cholesterol metabolism (acidic pathway) is known to synthesize two well-described vital regulators of cholesterol/lipid homeostasis

24(S)-Hydroxycholesterol as a Modulator of Neuronal Signaling and Survival.

Min-Yu Sun et al.

The Neuroscientist : a review journal bringing neurobiology, neurology and psychiatry, 22(2), 132-144 (2015-01-30)

The major cholesterol metabolite in brain, 24(S)-hydroxycholesterol (24S-HC), serves as a vehicle for cholesterol removal. Its effects on neuronal function, however, have only recently begun to be investigated. Here, we review that nascent work. Our own studies have demonstrated that

LXRα and LXRβ Nuclear Receptors Evolved in the Common Ancestor of Gnathostomes.

Elza Fonseca et al.

Genome biology and evolution, 9(1), 222-230 (2017-01-07)

Nuclear receptors (NRs) regulate numerous aspects of the endocrine system. They mediate endogenous and exogenous cues, ensuring a homeostatic control of development and metabolism. Gene duplication, loss and mutation have shaped the repertoire and function of NRs in metazoans. Here

Up-regulation of β-amyloidogenesis in neuron-like human cells by both 24- and 27-hydroxycholesterol: protective effect of N-acetyl-cysteine.

Paola Gamba et al.

Aging cell, 13(3), 561-572 (2014-03-13)

An abnormal accumulation of cholesterol oxidation products in the brain of patients with Alzheimer's disease (AD) would further link an impaired cholesterol metabolism in the pathogenesis of the disease. The first evidence stemming from the content of oxysterols in autopsy

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Global Trade Item Number

SKU	GTIN
SML1648-5MG	04061833058688
SML1648-1MG	04061826694350

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