Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H46O2 |
| Molecular Weight | 402.6529 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C
InChI
InChIKey=IOWMKBFJCNLRTC-XWXSNNQWSA-N
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
24S-hydroxycholesterol (24(S)-HC), the major cholesterol metabolite in the brain, is critical to brain cholesterol metabolism and turnover. This metabolite is a very potent, direct, and selective positive allosteric modulator of N-methyl-D-aspartate receptors (NMDARs) with a mechanism that does not overlap that of other allosteric modulators. NMDARs are glutamate-gated ion channels that are critical to the regulation of excitatory synaptic function in the CNS. It is known, that concentrations of 24(S)-HC in plasma and cerebrospinal fluid (CSF) are significantly higher in Alzheimer's disease and in mild cognitive impairment patients at early stages of the diseases compared to healthy subjects. It was suggested, that 24-hydroxycholesterol, could be a sensitive biomarker for the evaluation of these two diseases.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver. | 1993 Feb 24 |
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| Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile acid biosynthesis. | 1995 Feb |
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| Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. | 1997 Feb 7 |
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| Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol. | 2000 Jun 2 |
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| 24-hydroxycholesterol is a substrate for hepatic cholesterol 7alpha-hydroxylase (CYP7A). | 2000 Oct |
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| Key regulatory oxysterols in liver: analysis as delta4-3-ketone derivatives by HPLC and response to physiological perturbations. | 2001 Apr |
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| Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: abnormal levels of 24S- and 27-hydroxycholesterol. | 2001 Mar |
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| Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. | 2001 Oct 19 |
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| Human sterol 27-hydroxylase (CYP27) overexpressor transgenic mouse model. Evidence against 27-hydroxycholesterol as a critical regulator of cholesterol homeostasis. | 2002 Sep 13 |
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| Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003 Dec 9 |
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| Differential expression of cholesterol hydroxylases in Alzheimer's disease. | 2004 Aug 13 |
|
| Diagnostic use of cerebral and extracerebral oxysterols. | 2004 Feb |
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| Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease. | 2004 Jan |
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| Regulated expression of endothelial lipase by porcine brain capillary endothelial cells constituting the blood-brain barrier. | 2005 Jul |
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| Regulatory effects of synthetic liver X receptor- and peroxisome-proliferator activated receptor agonists on sterol transport pathways in polarized cerebrovascular endothelial cells. | 2006 |
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| Plasma cerebrosterol and magnetic resonance imaging measures in multiple sclerosis. | 2006 Jul |
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| Rediscovery of cerebrosterol. | 2007 Feb |
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| Regulation of alpha- and beta-secretase activity by oxysterols: cerebrosterol stimulates processing of APP via the alpha-secretase pathway. | 2007 Jul 20 |
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| [A new synthesis of cerebrosterol and its 24-epimer from lithocholic acid]. | 2007 Mar-Apr |
|
| 24S-hydroxycholesterol in relation to disease manifestations of acute experimental autoimmune encephalomyelitis. | 2007 May 15 |
|
| 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen. | 2007 Oct |
|
| Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells. | 2008 Dec |
|
| CYP46A1 variants influence Alzheimer's disease risk and brain cholesterol metabolism. | 2009 Apr |
|
| Oxidative damage in dengue fever. | 2009 Aug 15 |
|
| Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells. | 2009 Jan 6 |
|
| A second class of nuclear receptors for oxysterols: Regulation of RORalpha and RORgamma activity by 24S-hydroxycholesterol (cerebrosterol). | 2010 Aug |
|
| Dual roles of nuclear receptor liver X receptor α (LXRα) in the CYP3A4 expression in human hepatocytes as a positive and negative regulator. | 2013 Aug 1 |
Patents
Sample Use Guides
The concentration-response relationship of NMDAR modulation by 24(S)-hydroxycholesterol (24(S)-HC) was explored by preincubating hippocampal neurons for 40 s in increasing concentrations of compound (1-10000 nM) before agonist application. Potentiation value for 24(S)-HC was fit with the Hill equation. EC50 estimates was 1.2 μM for 24(S)-HC (N = 5 cells). Interestingly, 24(S)-HC was active at concentrations well below those measured in the CNS.
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474-73-7
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DTXSID101313419
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m6129
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C044563
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50515
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121948
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47IMW63S3F
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34310
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24S-Hydroxycholesterol
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PARENT (METABOLITE)
SUBSTANCE RECORD
