Home Other Building Blocks 27-Hydroxycholesterol

27-Hydroxycholesterol

CAS No.:
20380-11-4
Catalog Number:
AG00294D
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$119
- +
5mg
≥95%
1 week
United States
$354
- +
10mg
≥95%
1 week
United States
$619
- +
Product Description
Catalog Number:
AG00294D
Chemical Name:
27-Hydroxycholesterol
CAS Number:
20380-11-4
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
MDL Number:
MFCD00272990
IUPAC Name:
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChI:
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key:
FYHRJWMENCALJY-YSQMORBQSA-N
SMILES:
OC[C@@H](CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)C
UNII:
6T2NA6P5SQ
Properties
Complexity:
612  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
402.35g/mol
Formal Charge:
0
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
402.663g/mol
Monoisotopic Mass:
402.35g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
40.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.1  
Literature
Title Journal
The ROS-mediated activation of IL-6/STAT3 signaling pathway is involved in the 27-hydroxycholesterol-induced cellular senescence in nerve cells. Toxicology in vitro : an international journal published in association with BIBRA 20171201
27-Hydroxycholesterol regulates cholesterol synthesis and transport in C6 glioma cells. Neurotoxicology 20170301
The ROS-mediated activation of STAT-3/VEGF signaling is involved in the 27-hydroxycholesterol-induced angiogenesis in human breast cancer cells. Toxicology letters 20161215
27-Hydroxycholesterol and 7alpha-hydroxycholesterol trigger a sequence of events leading to migration of CCR5-expressing Th1 lymphocytes. Toxicology and applied pharmacology 20140201
Loading into nanoparticles improves quercetin's efficacy in preventing neuroinflammation induced by oxysterols. PloS one 20140101
Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein. The Journal of biological chemistry 20130322
Neonatal cholestasis with increased 3β-monohydroxy-Δ⁵ bile acids in serum and urine: not necessarily primary oxysterol 7α hydroxylase deficiency. Clinica chimica acta; international journal of clinical chemistry 20121009
Increased appearance rate of 27-hydroxycholesterol in vivo in hypercholesterolemia: a possible compensatory mechanism. Nutrition, metabolism, and cardiovascular diseases : NMCD 20121001
Cholesterol metabolism is associated with soluble amyloid precursor protein production in Alzheimer's disease. Journal of neurochemistry 20121001
Relationships of coronary heart disease with 27-hydroxycholesterol, low-density lipoprotein cholesterol, and menopausal hormone therapy. Circulation 20120925
Protective effects of 27- and 24-hydroxycholesterol against staurosporine-induced cell death in undifferentiated neuroblastoma SH-SY5Y cells. Neuroscience letters 20120906
27-hydroxycholesterol and the expression of three estrogen-sensitive proteins in MCF7 cells. Oncology reports 20120901
Increase of 27-hydroxycholesterol in the airways of patients with COPD: possible role of 27-hydroxycholesterol in tissue fibrosis. Chest 20120801
27-Hydroxycholesterol, does it exist? On the nomenclature and stereochemistry of 26-hydroxylated sterols. Steroids 20120501
Liver x receptor modulation of gene expression leading to proluteolytic effects in primate luteal cells. Biology of reproduction 20120301
Endoplasmic reticulum stress-induced CHOP activation mediates the down-regulation of leptin in human neuroblastoma SH-SY5Y cells treated with the oxysterol 27-hydroxycholesterol. Cellular signalling 20120201
side-chain-oxidized oxysterols upregulate ACE2 and Mas receptor in rat primary neurons. Neuro-degenerative diseases 20120101
Markers of cholesterol metabolism in the brain show stronger associations with cerebrovascular disease than Alzheimer's disease. Journal of Alzheimer's disease : JAD 20120101
The oxysterol, 27-hydroxycholesterol, links cholesterol metabolism to bone homeostasis through its actions on the estrogen and liver X receptors. Endocrinology 20111201
The oxysterol 27-hydroxycholesterol regulates α-synuclein and tyrosine hydroxylase expression levels in human neuroblastoma cells through modulation of liver X receptors and estrogen receptors--relevance to Parkinson's disease. Journal of neurochemistry 20111201
27-hydroxycholesterol induces the transition of MCF7 cells into a mesenchymal phenotype. Oncology reports 20110801
Oxysterols direct B-cell migration through EBI2. Nature 20110727
Side chain-oxidized oxysterols regulate the brain renin-angiotensin system through a liver X receptor-dependent mechanism. The Journal of biological chemistry 20110722
Biomarkers of oxidative damage in cigarette smokers: which biomarkers might reflect acute versus chronic oxidative stress? Free radical biology & medicine 20110615
Interaction between 24-hydroxycholesterol, oxidative stress, and amyloid-β in amplifying neuronal damage in Alzheimer's disease: three partners in crime. Aging cell 20110601
Marked accumulation of 27-hydroxycholesterol in the brains of Alzheimer's patients with the Swedish APP 670/671 mutation. Journal of lipid research 20110501
27-Hydroxycholesterol: the first identified endogenous SERM. Trends in endocrinology and metabolism: TEM 20110401
Plasma levels of 27-hydroxycholesterol in humans and mice with monogenic disturbances of high density lipoprotein metabolism. Atherosclerosis 20110201
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 of proteome research 20110107
Upregulation of brain renin angiotensin system by 27-hydroxycholesterol in Alzheimer's disease. Journal of Alzheimer's disease : JAD 20110101
Oxysterol derivatives of cholesterol in neurodegenerative disorders. Current medicinal chemistry 20110101
Silencing GADD153/CHOP gene expression protects against Alzheimer's disease-like pathology induced by 27-hydroxycholesterol in rabbit hippocampus. PloS one 20110101
The endogenous selective estrogen receptor modulator 27-hydroxycholesterol is a negative regulator of bone homeostasis. Endocrinology 20100801
Overexpression of steroidogenic acute regulatory protein increases macrophage cholesterol efflux to apolipoprotein AI. Cardiovascular research 20100601
Marked accumulation of 27-hydroxycholesterol in SPG5 patients with hereditary spastic paresis. Journal of lipid research 20100401
FTY720 stimulates 27-hydroxycholesterol production and confers atheroprotective effects in human primary macrophages. Circulation research 20100305
An alternative pathway of reverse cholesterol transport: the oxysterol 27-hydroxycholesterol. Atherosclerosis 20100301
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids. Biochimica et biophysica acta 20100101
Leptin reduces the accumulation of Abeta and phosphorylated tau induced by 27-hydroxycholesterol in rabbit organotypic slices. Journal of Alzheimer's disease : JAD 20100101
The oxysterol 27-hydroxycholesterol increases β-amyloid and oxidative stress in retinal pigment epithelial cells. BMC ophthalmology 20100101
Vitamin E and enzymatic/oxidative stress-driven oxysterols in amnestic mild cognitive impairment subtypes and Alzheimer's disease. Journal of Alzheimer's disease : JAD 20100101
Expression of sterol 27-hydroxylase in glial cells and its regulation by liver X receptor signaling. Neuroscience 20091201
LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms. Atherosclerosis 20091101
Plasma levels of 24S-hydroxycholesterol reflect brain volumes in patients without objective cognitive impairment but not in those with Alzheimer's disease. Neuroscience letters 20091002
Role of CYP27A1 in progesterone metabolism in vitro and in vivo. American journal of physiology. Endocrinology and metabolism 20091001
Effect of 27-hydroxycholesterol on survival and death of human macrophages and vascular smooth muscle cells. Free radical research 20091001
Regulation of fibroblast mitochondrial 27-hydroxycholesterol production by active plasma membrane cholesterol. Journal of lipid research 20090901
Oxidative damage in dengue fever. Free radical biology & medicine 20090815
Serum 24S-hydroxycholesterol and hippocampal size in middle-aged normal individuals. Neurobiology of aging 20090601
Interactions of oxysterols with membranes and proteins. Molecular aspects of medicine 20090601
Total cholesterol and oxysterols: early markers for cognitive decline in elderly? Neurobiology of aging 20090401
Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS. Journal of lipid research 20090201
Dopant assisted-atmospheric pressure photoionization (DA-APPI) liquid chromatography-mass spectrometry for the quantification of 27-hydroxycholesterol in plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090115
Activity-regulated cytoskeleton-associated protein in rodent brain is down-regulated by high fat diet in vivo and by 27-hydroxycholesterol in vitro. Brain pathology (Zurich, Switzerland) 20090101
Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells. Molecular neurodegeneration 20090101
Impact of 27-hydroxycholesterol on amyloid-beta peptide production and ATP-binding cassette transporter expression in primary human neurons. Journal of Alzheimer's disease : JAD 20090101
Hypercholesterolemia-induced Abeta accumulation in rabbit brain is associated with alteration in IGF-1 signaling. Neurobiology of disease 20081201
Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells. Journal of neurochemistry 20081201
Potential mechanisms linking cholesterol to Alzheimer's disease-like pathology in rabbit brain, hippocampal organotypic slices, and skeletal muscle. Journal of Alzheimer's disease : JAD 20081201
Regulation of alpha-synuclein expression by liver X receptor ligands in vitro. Neuroreport 20081119
27-Hydroxycholesterol: a potential endogenous regulator of estrogen receptor signaling. Trends in pharmacological sciences 20081001
Plasma oxysterols in normal and cholestatic children as indicators of the two pathways of bile acid synthesis. Clinica chimica acta; international journal of clinical chemistry 20080901
Plasma 24S-hydroxycholesterol and other oxysterols in acute closed head injury. Brain injury 20080701
Niemann-Pick C1 protects against atherosclerosis in mice via regulation of macrophage intracellular cholesterol trafficking. The Journal of clinical investigation 20080602
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine. American journal of physiology. Gastrointestinal and liver physiology 20080501
Effectors of rapid homeostatic responses of endoplasmic reticulum cholesterol and 3-hydroxy-3-methylglutaryl-CoA reductase. The Journal of biological chemistry 20080118
27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. Molecular endocrinology (Baltimore, Md.) 20080101
Glucocorticoid receptor-mediated upregulation of human CYP27A1, a potential anti-atherogenic enzyme. Biochimica et biophysica acta 20080101
Biosynthesis of the regulatory oxysterol, 5-cholesten-3beta,25-diol 3-sulfate, in hepatocytes. Journal of lipid research 20071201
27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen. Nature medicine 20071001
Lipoprotein distribution and biological variation of 24S- and 27-hydroxycholesterol in healthy volunteers. Atherosclerosis 20070901
Changes in classic and alternative pathways of bile acid synthesis in chronic liver disease. Clinica chimica acta; international journal of clinical chemistry 20070701
24S-hydroxycholesterol in relation to disease manifestations of acute experimental autoimmune encephalomyelitis. Journal of neuroscience research 20070515
Unique patient with cerebrotendinous xanthomatosis. Evidence for presence of a defect in a gene that is not identical to sterol 27-hydroxylase. Journal of internal medicine 20070501
Novel route for elimination of brain oxysterols across the blood-brain barrier: conversion into 7alpha-hydroxy-3-oxo-4-cholestenoic acid. Journal of lipid research 20070401
Osteopontin levels are associated with cholesterol synthesis markers in mildly hypercholesterolaemic patients. Acta cardiologica 20070401
PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine. Journal of lipid research 20070201
Enzymatic reduction of oxysterols impairs LXR signaling in cultured cells and the livers of mice. Cell metabolism 20070101
Crossing the barrier: oxysterols as cholesterol transporters and metabolic modulators in the brain. Journal of internal medicine 20061201
High-dose statin treatment does not alter plasma marker for brain cholesterol metabolism in patients with moderately elevated plasma cholesterol levels. Journal of clinical pharmacology 20060701
Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization. Organic letters 20060525
Short-term hepatic effects of depleted uranium on xenobiotic and bile acid metabolizing cytochrome P450 enzymes in the rat. Archives of toxicology 20060401
Biliary lipids, cholesterol and bile synthesis: different adaptive mechanisms to dietary cholesterol in lean and obese subjects. Alimentary pharmacology & therapeutics 20060401
27-Hydroxycholesterol causes remodeling in endothelial cell membrane lipid composition comparable to remodeling in the failed vein grafts of CABG patients. Life sciences 20060125
Effect of pravastatin on plasma sterols and oxysterols in men. European journal of clinical pharmacology 20060101
Oxysterols and Alzheimer's disease. Acta neurologica Scandinavica. Supplementum 20060101
Mitochondrial cholesterol transport: a possible target in the management of hyperlipidemia. Lipids 20051201
Crossing the barrier: net flux of 27-hydroxycholesterol into the human brain. Journal of lipid research 20050501
A minimally invasive technique for the evaluation of the regulatory steps of the two major pathways of bile acid synthesis. Clinica chimica acta; international journal of clinical chemistry 20050501
Detection of the steroidogenic acute regulatory protein, StAR, in human liver cells. Biochimica et biophysica acta 20050415
Regulation of sterol 27-hydroxylase in human monocyte-derived macrophages: up-regulation by transforming growth factor beta1. Biochimica et biophysica acta 20050221
Adipocytic differentiation and liver x receptor pathways regulate the accumulation of triacylglycerols in human vascular smooth muscle cells. The Journal of biological chemistry 20050204
Patients with atherosclerosis may have increased circulating levels of 27-hydroxycholesterol and cholestenoic acid. Scandinavian journal of clinical and laboratory investigation 20050101
Serum cholestenoic acid as a potential marker of pulmonary cholesterol homeostasis: increased levels in patients with pulmonary alveolar proteinosis. Journal of lipid research 20041201
Altered levels of plasma 24S- and 27-hydroxycholesterol in demented patients. Neuroscience letters 20040930
Differential expression of cholesterol hydroxylases in Alzheimer's disease. The Journal of biological chemistry 20040813
27-Hydroxycholesterol inhibits neutral sphingomyelinase in cultured human endothelial cells. Life sciences 20040813
Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry. Journal of lipid research 20040401
Diagnostic use of cerebral and extracerebral oxysterols. Clinical chemistry and laboratory medicine 20040201
Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease. Journal of lipid research 20040101
Significance of plasma 7alpha-hydroxy-4-cholesten-3-one and 27-hydroxycholesterol concentrations as markers for hepatic bile acid synthesis in cholesterol-fed rabbits. Metabolism: clinical and experimental 20040101
Novel sterols synthesized via the CYP27A1 metabolic pathway. Archives of biochemistry and biophysics 20031201
Clofibrate, a peroxisome-proliferator, enhances reverse cholesterol transport through cytochrome P450 activation and oxysterol generation. The Tohoku journal of experimental medicine 20031201
Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man. Free radical biology & medicine 20031015
On the origin of the cholestenoic acids in human circulation. Steroids 20030901
Effects of dietary 27-hydroxycholesterol on cholesterol metabolism and bile acid biosynthesis in the hamster. Canadian journal of physiology and pharmacology 20030901
27-Hydroxylation of 7- and 8-dehydrocholesterol in Smith-Lemli-Opitz syndrome: a novel metabolic pathway. Steroids 20030801
NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols. The Journal of biological chemistry 20030711
Side chain oxidized oxysterols in cerebrospinal fluid and the integrity of blood-brain and blood-cerebrospinal fluid barriers. Journal of lipid research 20030401
Expression of sterol 27-hydroxylase (CYP27A1) enhances cholesterol efflux. The Journal of biological chemistry 20030328
Marked induction of sterol 27-hydroxylase activity and mRNA levels during differentiation of human cultured monocytes into macrophages. Biochimica et biophysica acta 20030217
Serum cholesterol, precursors and metabolites and cognitive performance in an aging population. Neurobiology of aging 20030101
Transport of cholesterol into mitochondria is rate-limiting for bile acid synthesis via the alternative pathway in primary rat hepatocytes. The Journal of biological chemistry 20021213
Human sterol 27-hydroxylase (CYP27) overexpressor transgenic mouse model. Evidence against 27-hydroxycholesterol as a critical regulator of cholesterol homeostasis. The Journal of biological chemistry 20020913
Mechanism of accumulation of cholesterol and cholestanol in tendons and the role of sterol 27-hydroxylase (CYP27A1). Arteriosclerosis, thrombosis, and vascular biology 20020701
Regulation of oxysterol 7alpha-hydroxylase (CYP7B1) in primary cultures of rat hepatocytes. Hepatology (Baltimore, Md.) 20020601
Conversion of 7 alpha-hydroxycholesterol to bile acid in human subjects: is there an alternate pathway favoring cholic acid synthesis? The Journal of laboratory and clinical medicine 20020201
Oxysterols induce interleukin-1beta production in human macrophages. European journal of clinical investigation 20020101
Effect of deposited lipids in atheromatous lesions on the migration of vascular smooth muscle cells. Journal of atherosclerosis and thrombosis 20020101
Immune complexes and IFN-gamma decrease cholesterol 27-hydroxylase in human arterial endothelium and macrophages. Journal of lipid research 20011101
27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. The Journal of biological chemistry 20011019
Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. The Journal of biological chemistry 20011019
Overexpression of CYP27 in hepatic and extrahepatic cells: role in the regulation of cholesterol homeostasis. American journal of physiology. Gastrointestinal and liver physiology 20010701
Cholesterol dynamics in the foetal and neonatal brain as reflected by circulatory levels of 24S-hydroxycholesterol. Acta paediatrica (Oslo, Norway : 1992) 20010601
Selective distribution of oxysterols in atherosclerotic lesions and human plasma lipoproteins. Free radical research 20010501
Coronary atherosclerosis and oxidative stress as reflected by autoantibodies against oxidized low-density lipoprotein and oxysterols. Atherosclerosis 20010401
Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha. Journal of medicinal chemistry 20010315
Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: abnormal levels of 24S- and 27-hydroxycholesterol. Journal of lipid research 20010301
Cholesterol metabolism in primary biliary cirrhosis during simvastatin and UDCA administration. Journal of lipid research 20010301
A potential role for sterol 27-hydroxylase in atherogenesis. Atherosclerosis 20010201
Evidence that the major oxysterols in human circulation originate from distinct pools of cholesterol: a stable isotope study. Journal of lipid research 20010101
Oxysterol 7 alpha-hydroxylase activity by cholesterol 7 alpha-hydroxylase (CYP7A). The Journal of biological chemistry 20001103
24-hydroxycholesterol is a substrate for hepatic cholesterol 7alpha-hydroxylase (CYP7A). Journal of lipid research 20001001
Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol. The Journal of biological chemistry 20000602
Structure and functions of human oxysterol 7alpha-hydroxylase cDNAs and gene CYP7B1. Journal of lipid research 19991201
Oxysterol regulation of steroidogenic acute regulatory protein gene expression. Structural specificity and transcriptional and posttranscriptional actions. The Journal of biological chemistry 19981113
Activities of recombinant human cytochrome P450c27 (CYP27) which produce intermediates of alternative bile acid biosynthetic pathways. The Journal of biological chemistry 19980717
Sterol 27-hydroxylase: expression in human arterial endothelium. Journal of lipid research 19970601
Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols. Proceedings of the National Academy of Sciences of the United States of America 19970513
Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase. Biochimica et biophysica acta 19970218
Localization of sterol 27-hydroxylase immuno-reactivity in human atherosclerotic plaques. Biochimica et biophysica acta 19970218
Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. The Journal of biological chemistry 19970207
Effects of cyclosporin on cholesterol 27-hydroxylation and LDL receptor activity in HepG2 cells. Journal of lipid research 19960101
Esterification of oxysterols by human plasma lecithin-cholesterol acyltransferase. The Journal of biological chemistry 19950519
Effects of 26-aminocholesterol, 27-hydroxycholesterol, and 25-hydroxycholesterol on proliferation and cholesterol homeostasis in arterial myocytes. Arteriosclerosis, thrombosis, and vascular biology 19950301
7 Alpha-hydroxylation of 27-hydroxycholesterol in rat brain microsomes. Comptes rendus de l'Academie des sciences. Serie III, Sciences de la vie 19950301
Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile acid biosynthesis. Journal of lipid research 19950201
Synthesis of 27-hydroxycholesterol in rat liver mitochondria: HPLC assay and marked activation by exogenous cholesterol. Journal of lipid research 19930401
24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver. Biochimica et biophysica acta 19930224
Properties