The solvents recommended for this compound are as follows:
DMF: 2 mg/ml
DMSO: 3 mg/ml
Ethanol: 20 mg/ml
Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
SML1648
24(S)-Hydroxycholesterol
≥98% (HPLC)
Synonym(s):
24S-Hydroxycholesterol, 5-Cholesten-3β,24(S)-diol, Cerebrosterin, Cerebrosterol, Cholest-5-ene-3β,24-diol
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1 MG
€148.00
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€585.00
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1 MG
€148.00
5 MG
€585.00
About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.77
Recommended Products
Quality Level
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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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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Customers Also Viewed
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
Xiaofei Wei et al.
Neuropharmacology, 148, 11-20 (2018-12-31)
24S-hydroxycholesterol (24HC) is the major metabolic breakdown product of cholesterol in the brain. Among its other effects on neurons, 24HC modulates N-methyl-d-aspartate (NMDA or GluN) receptors, but our understanding of this mechanism is poor. We used whole-cell patch clamp recordings
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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