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
CC(C)[C@@H](O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
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
| Molecular Formula | C27H46O2 |
| Molecular Weight | 402.6529 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Dual roles of nuclear receptor liver X receptor α (LXRα) in the CYP3A4 expression in human hepatocytes as a positive and negative regulator. | 2013-08-01 |
|
| A second class of nuclear receptors for oxysterols: Regulation of RORalpha and RORgamma activity by 24S-hydroxycholesterol (cerebrosterol). | 2010-08 |
|
| Oxidative damage in dengue fever. | 2009-08-15 |
|
| CYP46A1 variants influence Alzheimer's disease risk and brain cholesterol metabolism. | 2009-04 |
|
| Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells. | 2009-01-06 |
|
| Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells. | 2008-12 |
|
| 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen. | 2007-10 |
|
| Regulation of alpha- and beta-secretase activity by oxysterols: cerebrosterol stimulates processing of APP via the alpha-secretase pathway. | 2007-07-20 |
|
| 24S-hydroxycholesterol in relation to disease manifestations of acute experimental autoimmune encephalomyelitis. | 2007-05-15 |
|
| [A new synthesis of cerebrosterol and its 24-epimer from lithocholic acid]. | 2007-05-05 |
|
| Rediscovery of cerebrosterol. | 2007-02 |
|
| Plasma cerebrosterol and magnetic resonance imaging measures in multiple sclerosis. | 2006-07 |
|
| Regulatory effects of synthetic liver X receptor- and peroxisome-proliferator activated receptor agonists on sterol transport pathways in polarized cerebrovascular endothelial cells. | 2006 |
|
| Regulated expression of endothelial lipase by porcine brain capillary endothelial cells constituting the blood-brain barrier. | 2005-07 |
|
| Differential expression of cholesterol hydroxylases in Alzheimer's disease. | 2004-08-13 |
|
| Diagnostic use of cerebral and extracerebral oxysterols. | 2004-02 |
|
| Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease. | 2004-01 |
|
| Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003-12-09 |
|
| Human sterol 27-hydroxylase (CYP27) overexpressor transgenic mouse model. Evidence against 27-hydroxycholesterol as a critical regulator of cholesterol homeostasis. | 2002-09-13 |
|
| Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. | 2001-10-19 |
|
| Key regulatory oxysterols in liver: analysis as delta4-3-ketone derivatives by HPLC and response to physiological perturbations. | 2001-04 |
|
| Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: abnormal levels of 24S- and 27-hydroxycholesterol. | 2001-03 |
|
| 24-hydroxycholesterol is a substrate for hepatic cholesterol 7alpha-hydroxylase (CYP7A). | 2000-10 |
|
| Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol. | 2000-06-02 |
|
| Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. | 1997-02-07 |
|
| Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile acid biosynthesis. | 1995-02 |
|
| 24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver. | 1993-02-24 |
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.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 19:35:12 GMT 2025
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on
Mon Mar 31 19:35:12 GMT 2025
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| Record UNII |
47IMW63S3F
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| Record Status |
Validated (UNII)
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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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34310
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24S-Hydroxycholesterol
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| Related Record | Type | Details | ||
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PARENT -> METABOLITE |
In human brain
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