Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

SML1648

Sigma-Aldrich

24(S)-Hydroxycholesterol

≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
474-73-7
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.77
Pricing and availability is not currently available.

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
SML2042H5884H1015
24(S)-Hydroxycholesterol ≥98% (HPLC)

SML1648

24(S)-Hydroxycholesterol

27-hydroxycholesterol ≥98% (HPLC)

SML2042

27-hydroxycholesterol

22(S)-Hydroxycholesterol

H5884

22(S)-Hydroxycholesterol

25-Hydroxycholesterol ≥98%

H1015

25-Hydroxycholesterol

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (TLC)

assay

≥98%

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

-

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

room temp

storage temp.

room temp

storage condition

desiccated

storage condition

-

storage condition

-

storage condition

-

solubility

DMSO: 3 mg/mL, clear (warmed)

solubility

DMSO: 2 mg/mL, clear (warmed)

solubility

-

solubility

-

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).
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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

    • Choose from one of the most recent versions:

    Certificates of Analysis (COA)

    Lot/Batch Number
    116M4710V

    Don't see the Right Version?

    If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

    Search for a COA

    Already Own This Product?

    Find documentation for the products that you have recently purchased in the Document Library.

    Visit the Document Library

    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
    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
    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
    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
    Martina Zandl-Lang et al.
    Biochimica et biophysica acta, 1863(1), 40-60 (2017-09-25)
    Amyloid-β peptides (Aβ) accumulate in cerebral capillaries indicating a central role of the blood-brain barrier (BBB) in the pathogenesis of Alzheimer's disease (AD). Although a relationship between apolipoprotein-, cholesterol- and Aβ metabolism is evident, the interconnecting mechanisms operating in brain
    View All Related Papers

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

    Contact Technical Service