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474-73-7,MFCD03695560
Catalog No.:AA00DDHH

474-73-7 | 24-Hydroxycholesterol

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DDHH
Chemical Name:
24-Hydroxycholesterol
CAS Number:
474-73-7
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
MDL Number:
MFCD03695560
SMILES:
OC1CCC2(C(=CCC3C2CCC2(C3CCC2C(CCC(C(C)C)O)C)C)C1)C
Properties
Properties
 
Form:
Solid  
MP:
181-184°C   
Storage:
2-8℃;  

Computed Properties
 
Complexity:
624  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
7  

Literature

Title: Loading into nanoparticles improves quercetin's efficacy in preventing neuroinflammation induced by oxysterols.

Journal: PloS one 20140101

Title: Dual roles of nuclear receptor liver X receptor α (LXRα) in the CYP3A4 expression in human hepatocytes as a positive and negative regulator.

Journal: Biochemical pharmacology 20130801

Title: Steady-state levels of retinal 24S-hydroxycholesterol are maintained by glial cells intervention after elevation of intraocular pressure in the rat.

Journal: Acta ophthalmologica 20121101

Title: Single nucleotide polymorphism in the cholesterol-24S-hydroxylase (CYP46A1) gene and its association with CFH and LOC387715 gene polymorphisms in age-related macular degeneration.

Journal: Investigative ophthalmology & visual science 20121009

Title: Cholesterol metabolism is associated with soluble amyloid precursor protein production in Alzheimer's disease.

Journal: Journal of neurochemistry 20121001

Title: Protective effects of 27- and 24-hydroxycholesterol against staurosporine-induced cell death in undifferentiated neuroblastoma SH-SY5Y cells.

Journal: Neuroscience letters 20120906

Title: Cholesterol loss during glutamate-mediated excitotoxicity.

Journal: The EMBO journal 20120404

Title: Interactions of amyloid β peptide 1-40 and cerebrosterol.

Journal: Neurochemical research 20120301

Title: side-chain-oxidized oxysterols upregulate ACE2 and Mas receptor in rat primary neurons.

Journal: Neuro-degenerative diseases 20120101

Title: Markers of cholesterol metabolism in the brain show stronger associations with cerebrovascular disease than Alzheimer's disease.

Journal: Journal of Alzheimer's disease : JAD 20120101

Title: Brain pericytes ABCA1 expression mediates cholesterol efflux but not cellular amyloid-β peptide accumulation.

Journal: Journal of Alzheimer's disease : JAD 20120101

Title: Enhanced production of 24S-hydroxycholesterol is not sufficient to drive liver X receptor target genes in vivo.

Journal: Journal of internal medicine 20111001

Title: 24S-hydroxycholesterol and cholesterol-24S-hydroxylase (CYP46A1) in the retina: from cholesterol homeostasis to pathophysiology of glaucoma.

Journal: Chemistry and physics of lipids 20110901

Title: Oxidative damage in ischemic stroke revealed using multiple biomarkers.

Journal: Stroke 20110801

Title: Side chain-oxidized oxysterols regulate the brain renin-angiotensin system through a liver X receptor-dependent mechanism.

Journal: The Journal of biological chemistry 20110722

Title: 24(S)-hydroxycholesterol induces neuronal cell death through necroptosis, a form of programmed necrosis.

Journal: The Journal of biological chemistry 20110715

Title: Biomarkers of oxidative damage in cigarette smokers: which biomarkers might reflect acute versus chronic oxidative stress?

Journal: Free radical biology & medicine 20110615

Title: Interaction between 24-hydroxycholesterol, oxidative stress, and amyloid-β in amplifying neuronal damage in Alzheimer's disease: three partners in crime.

Journal: Aging cell 20110601

Title: Cerebral accumulation of dietary derivable plant sterols does not interfere with memory and anxiety related behavior in Abcg5-/- mice.

Journal: Plant foods for human nutrition (Dordrecht, Netherlands) 20110601

Title: Quantification of cholesterol-metabolizing P450s CYP27A1 and CYP46A1 in neural tissues reveals a lack of enzyme-product correlations in human retina but not human brain.

Journal: Journal of proteome research 20110107

Title: Cholestenoic Acid is an important elimination product of cholesterol in the retina: comparison of retinal cholesterol metabolism with that in the brain.

Journal: Investigative ophthalmology & visual science 20110101

Title: Oxysterol derivatives of cholesterol in neurodegenerative disorders.

Journal: Current medicinal chemistry 20110101

Title: Plasma 24S-hydroxycholesterol levels in elderly subjects with late onset Alzheimer's disease or vascular dementia: a case-control study.

Journal: BMC neurology 20110101

Title: Cerebrospinal fluid and blood biomarkers of neuroaxonal damage in multiple sclerosis.

Journal: Multiple sclerosis international 20110101

Title: LXR-α genomics programmes neuronal death observed in Alzheimer's disease.

Journal: Apoptosis : an international journal on programmed cell death 20101201

Title: Modulators of the hedgehog signaling pathway.

Journal: Bioorganic & medicinal chemistry 20100915

Title: The effect of APOE genotype on brain levels of oxysterols in young and old human APOE epsilon2, epsilon3 and epsilon4 knock-in mice.

Journal: Neuroscience 20100811

Title: A second class of nuclear receptors for oxysterols: Regulation of RORalpha and RORgamma activity by 24S-hydroxycholesterol (cerebrosterol).

Journal: Biochimica et biophysica acta 20100801

Title: 24S-hydroxycholesterol effects on lipid metabolism genes are modeled in traumatic brain injury.

Journal: Brain research 20100310

Title: The antifungal drug voriconazole is an efficient inhibitor of brain cholesterol 24S-hydroxylase in vitro and in vivo.

Journal: Journal of lipid research 20100201

Title: Adeno-associated virus gene therapy with cholesterol 24-hydroxylase reduces the amyloid pathology before or after the onset of amyloid plaques in mouse models of Alzheimer's disease.

Journal: Molecular therapy : the journal of the American Society of Gene Therapy 20100101

Title: Effects of simvastatin on cholesterol metabolism and Alzheimer disease biomarkers.

Journal: Alzheimer disease and associated disorders 20100101

Title: Effects of cholesterol and its 24S-OH and 25-OH oxysterols on choline acetyltransferase-positive neurons in brain slices.

Journal: Pharmacology 20100101

Title: Primary open-angle glaucoma: association with cholesterol 24S-hydroxylase (CYP46A1) gene polymorphism and plasma 24-hydroxycholesterol levels.

Journal: Investigative ophthalmology & visual science 20091201

Title: Polar metabolite of cholesterol induces rat cognitive dysfunctions.

Journal: Neuroscience 20091201

Title: Plasma levels of 24S-hydroxycholesterol reflect brain volumes in patients without objective cognitive impairment but not in those with Alzheimer's disease.

Journal: Neuroscience letters 20091002

Title: 24-hydroxycholesterol sulfation by human cytosolic sulfotransferases: formation of monosulfates and disulfates, molecular modeling, sulfatase sensitivity, and inhibition of liver x receptor activation.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20091001

Title: Oxidative damage in dengue fever.

Journal: Free radical biology & medicine 20090815

Title: Serum 24S-hydroxycholesterol and hippocampal size in middle-aged normal individuals.

Journal: Neurobiology of aging 20090601

Title: Steroid and protein ligand binding to cytochrome P450 46A1 as assessed by hydrogen-deuterium exchange and mass spectrometry.

Journal: Biochemistry 20090519

Title: CYP46A1 variants influence Alzheimer's disease risk and brain cholesterol metabolism.

Journal: European psychiatry : the journal of the Association of European Psychiatrists 20090401

Title: Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS.

Journal: Journal of lipid research 20090201

Title: Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells.

Journal: Molecular neurodegeneration 20090101

Title: Oxysterols as markers of neurological disease--a review.

Journal: Scandinavian journal of clinical and laboratory investigation 20090101

Title: Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells.

Journal: Journal of neurochemistry 20081201

Title: A comparison of the potential unfavorable effects of oxycholesterol and oxyphytosterol in mice: different effects, on cerebral 24S-hydroxychoelsterol and serum triacylglycerols levels.

Journal: Bioscience, biotechnology, and biochemistry 20081201

Title: Plasma 24S-hydroxycholesterol and caudate MRI in pre-manifest and early Huntington's disease.

Journal: Brain : a journal of neurology 20081101

Title: Liquid chromatography-tandem mass spectrometry determination of plasma 24S-hydroxycholesterol with chromatographic separation of 25-hydroxycholesterol.

Journal: Analytical biochemistry 20081001

Title: Plasma 24S-hydroxycholesterol and other oxysterols in acute closed head injury.

Journal: Brain injury 20080701

Title: The effect of 24S-hydroxycholesterol on cholesterol homeostasis in neurons: quantitative changes to the cortical neuron proteome.

Journal: Journal of proteome research 20080401

Title: Complex of amyloid beta peptides with 24-hydroxycholesterol and its effect on hemicholinium-3 sensitive carriers.

Journal: Neurochemical research 20080301

Title: [Synthesis of sterols oxygenated in the terminal fragment of their side chains].

Journal: Bioorganicheskaia khimiia 20080101

Title: Brain-to-blood elimination of 24S-hydroxycholesterol from rat brain is mediated by organic anion transporting polypeptide 2 (oatp2) at the blood-brain barrier.

Journal: Journal of neurochemistry 20071101

Title: Degradation of 24S-hydroxycholesterol in men is not regulated by CYP7A1.

Journal: International journal of clinical pharmacology and therapeutics 20071101

Title: 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen.

Journal: Nature medicine 20071001

Title: Levels of ApoE in cerebrospinal fluid are correlated with Tau and 24S-hydroxycholesterol in patients with cognitive disorders.

Journal: Neuroscience letters 20070925

Title: Cholesterol biosynthesis pathway is disturbed in YAC128 mice and is modulated by huntingtin mutation.

Journal: Human molecular genetics 20070915

Title: Lipoprotein distribution and biological variation of 24S- and 27-hydroxycholesterol in healthy volunteers.

Journal: Atherosclerosis 20070901

Title: Plasma 24S hydroxycholesterol response to statins in Alzheimer's disease patients: effects of gender, CYP46, and ApoE polymorphisms.

Journal: Journal of molecular neuroscience : MN 20070901

Title: Regulation of alpha- and beta-secretase activity by oxysterols: cerebrosterol stimulates processing of APP via the alpha-secretase pathway.

Journal: Biochemical and biophysical research communications 20070720

Title: 24S-hydroxycholesterol in relation to disease manifestations of acute experimental autoimmune encephalomyelitis.

Journal: Journal of neuroscience research 20070515

Title: Unique patient with cerebrotendinous xanthomatosis. Evidence for presence of a defect in a gene that is not identical to sterol 27-hydroxylase.

Journal: Journal of internal medicine 20070501

Title: Liquid chromatography-mass spectrometry utilizing multi-stage fragmentation for the identification of oxysterols.

Journal: Journal of lipid research 20070401

Title: Oxysterols induced inflammation and oxidation in primary porcine retinal pigment epithelial cells.

Journal: Current eye research 20070301

Title: 24S-hydroxycholesterol induces cholesterol release from choroid plexus epithelial cells in an apical- and apoE isoform-dependent manner concomitantly with the induction of ABCA1 and ABCG1 expression.

Journal: Journal of neurochemistry 20070201

Title: Rediscovery of cerebrosterol.

Journal: Lipids 20070201

Title: Enzymatic reduction of oxysterols impairs LXR signaling in cultured cells and the livers of mice.

Journal: Cell metabolism 20070101

Title: [A new synthesis of cerebrosterol and its 24-epimer from lithocholic acid].

Journal: Bioorganicheskaia khimiia 20070101

Title: Crossing the barrier: oxysterols as cholesterol transporters and metabolic modulators in the brain.

Journal: Journal of internal medicine 20061201

Title: Plasma cerebrosterol and magnetic resonance imaging measures in multiple sclerosis.

Journal: Clinical neurology and neurosurgery 20060701

Title: High-dose statin treatment does not alter plasma marker for brain cholesterol metabolism in patients with moderately elevated plasma cholesterol levels.

Journal: Journal of clinical pharmacology 20060701

Title: Lovastatin modulates increased cholesterol and oxysterol levels and has a neuroprotective effect on rat hippocampal neurons after kainate injury.

Journal: Journal of neuropathology and experimental neurology 20060701

Title: 24(S)-hydroxycholesterol participates in a liver X receptor-controlled pathway in astrocytes that regulates apolipoprotein E-mediated cholesterol efflux.

Journal: The Journal of biological chemistry 20060505

Title: Polymorphism in ABCA1 influences CSF 24S-hydroxycholesterol levels but is not a major risk factor of Alzheimer's disease.

Journal: International journal of molecular medicine 20060501

Title: Cholesterol and 24S-hydroxycholesterol trafficking in Alzheimer's disease.

Journal: Expert review of neurotherapeutics 20060501

Title: Are the CSF levels of 24S-hydroxycholesterol a sensitive biomarker for mild cognitive impairment?

Journal: Neuroscience letters 20060401

Title: Polymorphism in neuropeptide Y influences CSF cholesterol levels but is no major risk factor of Alzheimer's disease.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20060201

Title: Circulating biomarkers of cognitive decline and dementia.

Journal: Clinica chimica acta; international journal of clinical chemistry 20060201

Title: Effect of pravastatin on plasma sterols and oxysterols in men.

Journal: European journal of clinical pharmacology 20060101

Title: Regulatory effects of synthetic liver X receptor- and peroxisome-proliferator activated receptor agonists on sterol transport pathways in polarized cerebrovascular endothelial cells.

Journal: The international journal of biochemistry & cell biology 20060101

Title: Cholesterol metabolism in the brain: importance of 24S-hydroxylation.

Journal: Acta neurologica Scandinavica. Supplementum 20060101

Title: Oxysterols and Alzheimer's disease.

Journal: Acta neurologica Scandinavica. Supplementum 20060101

Title: Influence of peroxisome proliferator-activated receptor gamma gene polymorphism on 24S-hydroxycholesterol levels in Alzheimer's patients.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20051001

Title: Regulated expression of endothelial lipase by porcine brain capillary endothelial cells constituting the blood-brain barrier.

Journal: Journal of neurochemistry 20050701

Title: A cluster of cholesterol-related genes confers susceptibility for Alzheimer's disease.

Journal: The Journal of clinical psychiatry 20050701

Title: 24S-hydroxycholesterol induces inflammatory gene expression in primary human neural cells.

Journal: Neuroreport 20050621

Title: Effect of raloxifene and hormone therapy on serum markers of brain and whole-body cholesterol metabolism in postmenopausal women.

Journal: Maturitas 20050411

Title: Biological markers in CSF and blood for axonal degeneration in multiple sclerosis.

Journal: The Lancet. Neurology 20050101

Title: Altered levels of plasma 24S- and 27-hydroxycholesterol in demented patients.

Journal: Neuroscience letters 20040930

Title: Does brain specific 24S-hydroxycholesterol in plasma indicate the disruption of the blood-brain barrier in patients with ischemic stroke?

Journal: Neuroscience letters 20040923

Title: Cholesterol in neurologic disorders of the elderly: stroke and Alzheimer's disease.

Journal: Neurobiology of aging 20040901

Title: Differential expression of cholesterol hydroxylases in Alzheimer's disease.

Journal: The Journal of biological chemistry 20040813

Title: High doses of simvastatin, pravastatin, and cholesterol reduce brain cholesterol synthesis in guinea pigs.

Journal: Steroids 20040601

Title: Brain cholesterol: long secret life behind a barrier.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040501

Title: Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry.

Journal: Journal of lipid research 20040401

Title: Diagnostic use of cerebral and extracerebral oxysterols.

Journal: Clinical chemistry and laboratory medicine 20040201

Title: The effects of gender and CYP46 and apo E polymorphism on 24S-hydroxycholesterol levels in Alzheimer's patients treated with statins.

Journal: Current Alzheimer research 20040201

Title: Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease.

Journal: Journal of lipid research 20040101

Title: Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain.

Journal: Biochemistry 20031209

Title: Combination of serum markers related to several mechanisms in Alzheimer's disease.

Journal: Neurobiology of aging 20031101

Title: 24S-hydroxycholesterol: a marker of brain cholesterol metabolism.

Journal: Pharmacopsychiatry 20030901

Title: Decreased levels of the brain specific 24S-hydroxycholesterol and cholesterol precursors in serum of multiple sclerosis patients.

Journal: Neuroscience letters 20030828

Title: On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation.

Journal: Journal of lipid research 20030801

Title: Side chain oxidized oxysterols in cerebrospinal fluid and the integrity of blood-brain and blood-cerebrospinal fluid barriers.

Journal: Journal of lipid research 20030401

Title: Reduction in levels of 24S-hydroxycholesterol by statin treatment in patients with Alzheimer disease.

Journal: Archives of neurology 20030401

Title: Serum cholesterol, precursors and metabolites and cognitive performance in an aging population.

Journal: Neurobiology of aging 20030101

Title: Increased brain beta-amyloid load, phosphorylated tau, and risk of Alzheimer disease associated with an intronic CYP46 polymorphism.

Journal: Archives of neurology 20030101

Title: The role of 24S-hydroxycholesterol in Alzheimer's disease.

Journal: The journal of nutrition, health & aging 20030101

Title: Changes in human plasma levels of the brain specific oxysterol 24S-hydroxycholesterol during progression of multiple sclerosis.

Journal: Neuroscience letters 20021018

Title: Human sterol 27-hydroxylase (CYP27) overexpressor transgenic mouse model. Evidence against 27-hydroxycholesterol as a critical regulator of cholesterol homeostasis.

Journal: The Journal of biological chemistry 20020913

Title: Cerebrospinal fluid 24S-hydroxycholesterol is increased in patients with Alzheimer's disease compared to healthy controls.

Journal: Neuroscience letters 20020510

Title: Reduction of plasma 24S-hydroxycholesterol (cerebrosterol) levels using high-dosage simvastatin in patients with hypercholesterolemia: evidence that simvastatin affects cholesterol metabolism in the human brain.

Journal: Archives of neurology 20020201

Title: 24S-hydroxycholesterol in cerebrospinal fluid is elevated in early stages of dementia.

Journal: Journal of psychiatric research 20020101

Title: Polymorphism in the cholesterol 24S-hydroxylase gene is associated with Alzheimer's disease.

Journal: Molecular psychiatry 20020101

Title: On the turnover of brain cholesterol in patients with Alzheimer's disease. Abnormal induction of the cholesterol-catabolic enzyme CYP46 in glial cells.

Journal: Neuroscience letters 20011113

Title: Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4.

Journal: The Journal of biological chemistry 20011019

Title: From brain to bile. Evidence that conjugation and omega-hydroxylation are important for elimination of 24S-hydroxycholesterol (cerebrosterol) in humans.

Journal: The Journal of biological chemistry 20011005

Title: Cholesterol dynamics in the foetal and neonatal brain as reflected by circulatory levels of 24S-hydroxycholesterol.

Journal: Acta paediatrica (Oslo, Norway : 1992) 20010601

Title: Key regulatory oxysterols in liver: analysis as delta4-3-ketone derivatives by HPLC and response to physiological perturbations.

Journal: Journal of lipid research 20010401

Title: Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.

Journal: Journal of medicinal chemistry 20010315

Title: Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: abnormal levels of 24S- and 27-hydroxycholesterol.

Journal: Journal of lipid research 20010301

Title: Evidence that the major oxysterols in human circulation originate from distinct pools of cholesterol: a stable isotope study.

Journal: Journal of lipid research 20010101

Title: Neurotoxicity of 24-hydroxycholesterol, an important cholesterol elimination product of the brain, may be prevented by vitamin E and estradiol-17beta.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20010101

Title: 24-hydroxycholesterol is a substrate for hepatic cholesterol 7alpha-hydroxylase (CYP7A).

Journal: Journal of lipid research 20001001

Title: Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol.

Journal: The Journal of biological chemistry 20000602

Title: Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway.

Journal: The Journal of biological chemistry 19970207

Title: Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile acid biosynthesis.

Journal: Journal of lipid research 19950201

Title: 24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver.

Journal: Biochimica et biophysica acta 19930224

Title: Yuki Kimura, et al. Tocopherol suppresses 24(S)-hydroxycholesterol-induced cell death via inhibition of CaMKII phosphorylation. Biochimie. 2018 Oct;153:203-209.

Title: M Shafaati, et al. Enhanced production of 24S-hydroxycholesterol is not sufficient to drive liver X receptor target genes in vivo. J Intern Med. 2011 Oct;270(4):377-87.

Title: Steven M Paul, et al. The major brain cholesterol metabolite 24(S)-hydroxycholesterol is a potent allosteric modulator of N-methyl-D-aspartate receptors. J Neurosci. 2013 Oct 30;33(44):17290-300.

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Tags:474-73-7 Molecular Formula|474-73-7 MDL|474-73-7 SMILES|474-73-7 24-Hydroxycholesterol