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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
0000543498
0000543498
0000402311
0000402311
0000296341

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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
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Global Trade Item Number

SKUGTIN
SML1648-1MG04061826694350
SML1648-5MG04061833058688