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SML1648

24(S)-Hydroxycholesterol

≥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

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.

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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
116M4710V

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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
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

Global Trade Item Number

SKUGTIN
SML1648-1MG04061826694350
SML1648-5MG04061833058688