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cholesteryl linoleate
cholesterol 1-(9Z,12Z-octadecadienoate)

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Name:[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z)-octadeca-9,12-dienoate
CAS Number: 604-33-1Picture of molecule3D/inchi
Other(deleted CASRN):100339-48-8
ECHA EINECS - REACH Pre-Reg:210-065-9
FDA UNII: 75427237HI
Nikkaji Web:J150.304I
Beilstein Number:2343143
MDL:MFCD00003644
XlogP3-AA:15.90 (est)
Molecular Weight:649.09912000
Formula:C45 H76 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 677.30 °C. @ 760.00 mm Hg (est)
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): 18.170 (est)
Soluble in:
 water, 1.653e-013 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Linoleic Acid Cholesterol Ester 95%
Santa Cruz Biotechnology
For experimental / research use only.
Cholesteryl Linoleate
Sigma-Aldrich: Sigma
For experimental / research use only.
Cholesteryl Linoleate ≥98% (HPLC; detection at 205 nm)
sds
TCI AMERICA
For experimental / research use only.
Cholesterol Linoleate >95.0%(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for cholesteryl linoleate usage levels up to:
 not for fragrance use.
 
Recommendation for cholesteryl linoleate flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):604-33-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5287939
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z)-octadeca-9,12-dienoate
Chemidplus:0000604331
 
References:
 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z)-octadeca-9,12-dienoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5287939
Pubchem (sid):135050401
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C15441
HMDB (The Human Metabolome Database):HMDB00610
FooDB:FDB022141
Export Tariff Code:2937.29.9090
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
(Z,Z)-(3b)-cholest-5-en-3-ol 9,12-octadecadienoate
(3b)-cholest-5-en-3-yl (9Z,12Z)-9,12-octadecadienoate
(3a,8a,17a)-cholest-5-en-3-yl (9Z,12Z)-octadeca-9,12-dienoate
(3b)-cholest-5-en-3-yl (9Z,12Z)-octadeca-9,12-dienoate
 cholesterol 1-(9Z,12Z-octadecadienoate)
 cholesterol 1-linoleoate
 cholesterol linoleate
 cholesterol, linoleate (8CI)
 cholesteryl 1-(9Z,12Z-octadecadienoate)
 cholesteryl 1-linoleoate
 cholesteryllinoleate
[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z)-octadeca-9,12-dienoate
 linoleic acid cholesteryl ester
 linoleic acid, cholesteryl ester
1-linoleoyl-cholesterol
9,12-octadecadienoic acid, (3a)-cholest-5-en-3-yl ester, (9Z,12Z)-
9,12-octadecadienoic acid, (3b)-cholest-5-en-3-yl ester, (9Z,12Z)-
 

Articles:

PubMed:Release and Capture of Bioactive Oxidized Phospholipids and Oxidized Cholesteryl Esters During Percutaneous Coronary and Peripheral Arterial Interventions in Humans.
PubMed:LDL cholesterol recycles to the plasma membrane via a Rab8a-Myosin5b-actin-dependent membrane transport route.
PubMed:Cholesteryl ester species differently elevate plasma cholesterol in hamsters.
PubMed:Effects of aerobic exercise on lipid-effector molecules of the innate immune response.
PubMed:Modified lipoprotein-derived lipid particles accumulate in human stenotic aortic valves.
PubMed:Occurrence of cytotoxic 9-oxononanoyl secosterol aldehydes in human low-density lipoprotein.
PubMed:The regional ratio of cholesteryl palmitate to cholesteryl oleate measured by ToF-SIMS as a key parameter of atherosclerosis.
PubMed:Diet-induced alterations of host cholesterol metabolism are likely to affect the gut microbiota composition in hamsters.
PubMed:The Chlamydia trachomatis CT149 protein exhibits esterase activity in vitro and catalyzes cholesteryl ester hydrolysis when expressed in HeLa cells.
PubMed:Cholesteryl ester acyl oxidation and remodeling in murine macrophages: formation of oxidized phosphatidylcholine.
PubMed:Electrospray MS/MS reveals extensive and nonspecific oxidation of cholesterol esters in human peripheral vascular lesions.
PubMed:Lipid markers of "geometrical" radical stress: synthesis of monotrans cholesteryl ester isomers and detection in human plasma.
PubMed:Accumulation and aberrant composition of cholesteryl esters in Scrapie-infected N2a cells and C57BL/6 mouse brains.
PubMed:Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro.
PubMed:Intramural coronary lipid injection induces atheromatous lesions expressing proinflammatory chemokines: implications for the development of a porcine model of atherosclerosis.
PubMed:Pyripyropene A, an acyl-coenzyme A:cholesterol acyltransferase 2-selective inhibitor, attenuates hypercholesterolemia and atherosclerosis in murine models of hyperlipidemia.
PubMed:Modification of composition of a nanoemulsion with different cholesteryl ester molecular species: effects on stability, peroxidation, and cell uptake.
PubMed:The serum fatty acids myristic acid and linoleic acid are better predictors of serum cholesterol concentrations when measured as molecular percentages rather than as absolute concentrations.
PubMed:The core-aldehyde 9-oxononanoyl cholesterol increases the level of transforming growth factor beta1-specific receptors on promonocytic U937 cell membranes.
PubMed:LDL cholesteryl oleate as a predictor for atherosclerosis: evidence from human and animal studies on dietary fat.
PubMed:Transport of LDL-derived cholesterol from the NPC1 compartment to the ER involves the trans-Golgi network and the SNARE protein complex.
PubMed:Lipids including cholesteryl linoleate and cholesteryl arachidonate contribute to the inherent antibacterial activity of human nasal fluid.
PubMed:Macrophage activation induces formation of the anti-inflammatory lipid cholesteryl-nitrolinoleate.
PubMed:Hexadecylphosphocholine interferes with the intracellular transport of cholesterol in HepG2 cells.
PubMed:Paraoxonase and platelet-activating factor acetylhydrolase activities in lipoproteins of beta-thalassemia/hemoglobin E patients.
PubMed:Detection of cholesteryl ester hydroperoxide isomers using gas chromatography-mass spectrometry combined with thin-layer chromatography blotting.
PubMed:ABCA1 overexpression in the liver of LDLr-KO mice leads to accumulation of pro-atherogenic lipoproteins and enhanced atherosclerosis.
PubMed:Roles of endogenously synthesized sterols in the endocytic pathway.
PubMed:The reduction of cholesteryl linoleate in lipoproteins: an index of clinical severity in beta-thalassemia/Hb E.
PubMed:Serum fatty acids as biomarkers of fat intake predict serum cholesterol concentrations in a population-based survey of New Zealand adolescents and adults.
PubMed:Expression and synthesis of TGFbeta1 is induced in macrophages by 9-oxononanoyl cholesterol, a major cholesteryl ester oxidation product.
PubMed:Identification of 9-hydroxyoctadecadienoic acid and other oxidized free fatty acids as ligands of the G protein-coupled receptor G2A.
PubMed:Selective uptake and efflux of cholesteryl linoleate in LDL by macrophages expressing 12/15-lipoxygenase.
PubMed:Lipoprotein-like particles and cholesteryl esters in human Bruch's membrane: initial characterization.
PubMed:Endovascular needle injection of cholesteryl linoleate into the arterial wall produces complex vascular lesions identifiable by intravascular ultrasound: early development in a porcine model of vulnerable plaque.
PubMed:Cholesterol esterase action on human high density lipoproteins and inhibition studies: detection by MALDI-TOF MS.
PubMed:Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins.
PubMed:Pravastatin sodium, an inhibitor of HMG-CoA reductase, decreases HDL cholesterol by transfer of cholesteryl ester from HDL to VLDL in Japanese white rabbits.
PubMed:Omapatrilat decreased macrophage oxidative status and atherosclerosis progression in atherosclerotic apolipoprotein E-deficient mice.
PubMed:Effects of LDL, cholesterol, and their oxidized forms on the precipitation kinetics of calcium phosphates.
PubMed:Vitamin C inhibits lipid oxidation in human HDL.
PubMed:Sequence of the lid affects activity and specificity of Candida rugosa lipase isoenzymes.
PubMed:Cholesteryl ester oxidation products in atherosclerosis.
PubMed:Autoantibody-mediated atherosclerosis.
PubMed:Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins.
PubMed:Lipid peroxidation and nitric oxide inactivation in postmenopausal women.
PubMed:Lipid peroxidation and vitamin E in human coronary atherosclerotic lesions.
PubMed:Transient experimental anemia in cholesterol-fed rabbits induces systemic overexpression of the reticulocyte-type 15-lipoxygenase and protects from aortic lipid deposition.
PubMed:Synthesis and biochemical properties of a new photoactivatable cholesterol analog 7,7-azocholestanol and its linoleate ester in Chinese hamster ovary cell lines.
PubMed:Determination of the alpha-tocopherol inhibition rate constant for peroxidation in low-density lipoprotein.
PubMed:Preparation of the addition products of alpha-tocopherol with cholesteryl linoleate-peroxyl radicals.
PubMed:Oxidized cholesteryl linoleates stimulate endothelial cells to bind monocytes via the extracellular signal-regulated kinase 1/2 pathway.
PubMed:In vivo contribution of LCAT to apolipoprotein B lipoprotein cholesteryl esters in LDL receptor and apolipoprotein E knockout mice.
PubMed:Thin-layer chromatography blotting for the fluorescence detection of phospholipid hydroperoxides and cholesteryl ester hydroperoxides.
PubMed:Estradiol esterification in the human preovulatory follicle.
PubMed:Supplementation of postmenopausal women with fish oil does not increase overall oxidation of LDL ex vivo compared to dietary oils rich in oleate and linoleate.
PubMed:Fate of lipid hydroperoxides in blood plasma.
PubMed:Design of unsymmetrical azo initiators to increase radical generation efficiency in low-density lipoproteins.
PubMed:Normal high density lipoprotein inhibits three steps in the formation of mildly oxidized low density lipoprotein: steps 2 and 3.
PubMed:Niemann-pick type C1 (NPC1) overexpression alters cellular cholesterol homeostasis.
PubMed:Presence of regio-isomeric cholesteryl linoleate hydroperoxides and hydroxides in plasma from healthy humans as evidence of free radical-mediated lipid peroxidation in vivo.
PubMed:Low density lipoprotein as a carrier of cytostatics in cancer chemotherapy: study of stability of drug-carrier complexes in blood.
PubMed:Human serum paraoxonases (PON1) Q and R selectively decrease lipid peroxides in human coronary and carotid atherosclerotic lesions: PON1 esterase and peroxidase-like activities.
PubMed:Macrophages can decrease the level of cholesteryl ester hydroperoxides in low density lipoprotein.
PubMed:Regioisomeric distribution of cholesteryl linoleate hydroperoxides and hydroxides in plasma from healthy humans provides evidence for free radical-mediated lipid peroxidation in vivo.
PubMed:Downregulation by tumor necrosis factor-alpha of monocyte CCR2 expression and monocyte chemotactic protein-1-induced transendothelial migration is antagonized by oxidized low-density lipoprotein: a potential mechanism of monocyte retention in atherosclerotic lesions.
PubMed:Coexistence of oxidized lipids and alpha-tocopherol in all lipoprotein density fractions isolated from advanced human atherosclerotic plaques.
PubMed:Macrophage-enhanced formation of cholesteryl ester-core aldehydes during oxidation of low density lipoprotein.
PubMed:Time-dependent changes to lipids and antioxidants in plasma and aortas of apolipoprotein E knockout mice.
PubMed:Human serum paraoxonase (PON 1) is inactivated by oxidized low density lipoprotein and preserved by antioxidants.
PubMed:When and why a water-soluble antioxidant becomes pro-oxidant during copper-induced low-density lipoprotein oxidation: a study using uric acid.
PubMed:Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits.
PubMed:Monoclonal autoantibodies specific for oxidized phospholipids or oxidized phospholipid-protein adducts inhibit macrophage uptake of oxidized low-density lipoproteins.
PubMed:Immunization of LDL receptor-deficient mice with homologous malondialdehyde-modified and native LDL reduces progression of atherosclerosis by mechanisms other than induction of high titers of antibodies to oxidative neoepitopes.
PubMed:LDL size distribution in relation to insulin sensitivity and lipoprotein pattern in young and healthy subjects.
PubMed:Accumulation and metabolism of low density lipoprotein-derived cholesteryl linoleate hydroperoxide and hydroxide by macrophages.
PubMed:Quantitative analysis of cholesterol and cholesteryl esters in human atherosclerotic plaques using near-infrared Raman spectroscopy.
PubMed:The rabbit 15-lipoxygenase preferentially oxygenates LDL cholesterol esters, and this reaction does not require vitamin E.
PubMed:Femtomole analysis of 9-oxononanoyl cholesterol by high performance liquid chromatography.
PubMed:Cholesteryl hydroperoxyoctadecadienoate from oxidized low density lipoprotein inactivates platelet-derived growth factor.
PubMed:Direct observation of lipoprotein cholesterol ester degradation in lysosomes.
PubMed:Paraoxonase inhibits high-density lipoprotein oxidation and preserves its functions. A possible peroxidative role for paraoxonase.
PubMed:High-density lipoprotein (HDL3)-associated alpha-tocopherol is taken up by HepG2 cells via the selective uptake pathway and resecreted with endogenously synthesized apo-lipoprotein B-rich lipoprotein particles.
PubMed:The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation.
PubMed:Copper can promote oxidation of LDL by markedly different mechanisms.
PubMed:Oxidation of high density lipoproteins. II. Evidence for direct reduction of lipid hydroperoxides by methionine residues of apolipoproteins AI and AII.
PubMed:Cholesteryl ester hydroperoxide formation in myoglobin-catalyzed low density lipoprotein oxidation: concerted antioxidant activity of caffeic and p-coumaric acids with ascorbate.
PubMed:Intracellular trafficking of the free cholesterol derived from LDL cholesteryl ester is defective in vivo in Niemann-Pick C disease: insights on normal metabolism of HDL and LDL gained from the NP-C mutation.
PubMed:Separation and characterization of cholesteryl oxo- and hydroxy-linoleate isolated from human atherosclerotic plaque.
PubMed:Oxidation of free fatty acids in low density lipoprotein by 15-lipoxygenase stimulates nonenzymic, alpha-tocopherol-mediated peroxidation of cholesteryl esters.
PubMed:Interactions between lifestyle-related factors and the ApoE polymorphism on plasma lipids and apolipoproteins. The EARS Study. European Atherosclerosis Research Study.
PubMed:The fate of cholesterol exiting lysosomes.
PubMed:Lysophosphatidylcholine promotes cholesterol efflux from mouse macrophage foam cells.
PubMed:Oxidation products of cholesteryl linoleate are resistant to hydrolysis in macrophages, form complexes with proteins, and are present in human atherosclerotic lesions.
PubMed:Toxicity of polyunsaturated fatty acid esters for human monocyte-macrophages: the anomalous behaviour of cholesteryl linolenate.
PubMed:Role of alpha-tocopheroxyl radical in the initiation of lipid peroxidation in human low-density lipoprotein exposed to horse radish peroxidase.
PubMed:Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation.
PubMed:Oxidation of LDL by recombinant human 15-lipoxygenase: evidence for alpha-tocopherol-dependent oxidation of esterified core and surface lipids.
PubMed:Disappearance of two major phosphatidylcholines from plasma is predominantly via LCAT and hepatic lipase.
PubMed:Phagocytosis of mast cell granule remnant-bound LDL by smooth muscle cells of synthetic phenotype: a scavenger receptor-mediated process that effectively stimulates cytoplasmic cholesteryl ester synthesis.
PubMed:Catalytic properties of the purified rat hepatic cytosolic cholesteryl ester hydrolase.
PubMed:Identification and quantification of regioisomeric cholesteryl linoleate hydroperoxides in oxidized human low density lipoprotein and high density lipoprotein.
PubMed:Slow beta-migrating lipoprotein: an atherogenic subclass of low density lipoproteins.
PubMed:Reaction of phosphatidylcholine hydroperoxide in human plasma: the role of peroxidase and lecithin:cholesterol acyltransferase.
PubMed:Rapid reduction and removal of HDL- but not LDL-associated cholesteryl ester hydroperoxides by rat liver perfused in situ.
PubMed:Peroxidized low-density lipoprotein with four kinds of hydroperoxidized cholesteryl linoleate estimated in plasma of young heavy smokers.
PubMed:Chemical characterization of peroxidized low-density lipoprotein in plasma and aortic atheroma.
PubMed:Coulometric detection in high-performance liquid chromatographic analysis of cholesteryl ester hydroperoxides.
PubMed:Dietary antioxidants and cigarette smoke-induced biomolecular damage: a complex interaction.
PubMed:Effects of the neutral lipid content of high density lipoprotein on apolipoprotein A-I structure and particle stability.
PubMed:Human atherosclerotic plaque contains both oxidized lipids and relatively large amounts of alpha-tocopherol and ascorbate.
PubMed:Exchange of oxidized cholesteryl linoleate between LDL and HDL mediated by cholesteryl ester transfer protein.
PubMed:The inhibition of foam cell formation by sodium diethyldithiocarbamate.
PubMed:High-performance liquid chromatography with mercury cathode electrochemical detection: application to lipid hydroperoxide analysis.
PubMed:Dietary polyunsaturated fat modifies low-density lipoproteins and reduces atherosclerosis of nonhuman primates with high and low diet responsiveness.
PubMed:Microsomal glutathione transferase: lipid-derived substrates and lipid dependence.
PubMed:Lipoxygenase contributes to the oxidation of lipids in human atherosclerotic plaques.
PubMed:Phase behavior and crystalline structures of cholesteryl ester mixtures: a C-13 MASNMR study.
PubMed:HDL-mediated efflux of intracellular cholesterol is impaired in fibroblasts from Tangier disease patients.
PubMed:EDTA differentially and incompletely inhibits components of prolonged cell-mediated oxidation of low-density lipoprotein.
PubMed:Progesterone stimulation of HMG-CoA reductase activity in cultured cells.
PubMed:Structure of uncomplexed and linoleate-bound Candida cylindracea cholesterol esterase.
PubMed:The influence of cholesteryl ester content on hepatocyte triolein emulsion uptake.
PubMed:Free radical scavenging properties of apomorphine enantiomers and dopamine: possible implication in their mechanism of action in parkinsonism.
PubMed:Lipid oxidation, lipoprotein cell-association and ceroid accumulation in P388D1 macrophage-like cells.
PubMed:Human blood cells support the reduction of low-density-lipoprotein-associated cholesteryl ester hydroperoxides by albumin-bound ebselen.
PubMed:Predominance of esterified hydroperoxy-linoleic acid in human monocyte-oxidized LDL.
PubMed:Development of the atherosclerotic core region. Chemical and ultrastructural analysis of microdissected atherosclerotic lesions from human aorta.
PubMed:Biomarkers of dietary fat composition in young adults with a parental history of premature coronary heart disease compared with controls. The EARS Study.
PubMed:Combined effects of magnesium deficiency and an atherogenic level of low density lipoprotein on uptake and metabolism of low density lipoprotein by cultured human endothelial cells. I. Biochemical data.
PubMed:Cholesteryl esters on the body surfaces of the camel tick, Hyalomma dromedarii (Koch, 1844) and the brown dog tick, Rhipicephalus sanguineus (Latreille, 1806).
PubMed:ACAT inhibition decreases LDL cholesterol in rabbits fed a cholesterol-free diet. Marked changes in LDL cholesterol without changes in LDL receptor mRNA abundance.
PubMed:Reduction of HDL- and LDL-associated cholesterylester and phospholipid hydroperoxides by phospholipid hydroperoxide glutathione peroxidase and Ebselen (PZ 51).
PubMed:Differing effects of probucol and vitamin E on the oxidation of lipoproteins, ceroid accumulation and protein uptake by macrophages.
PubMed:Cholesterol oxidation in muscle tissue.
PubMed:Plasma peroxidized low-density lipoprotein with hydroperoxidized cholesteryl linoleates estimated in patients with familial hypercholesterolemia.
PubMed:Greater selective uptake by Hep G2 cells of high-density lipoprotein cholesteryl ester hydroperoxides than of unoxidized cholesteryl esters.
PubMed:The oxidation of blood plasma and low density lipoprotein components by chemically generated singlet oxygen.
PubMed:A method for defining the stages of low-density lipoprotein oxidation by the separation of cholesterol- and cholesteryl ester-oxidation products using HPLC.
PubMed:The role of subfractions of high density lipoprotein in the in vivo transport of cholesterol from cholesterol-loaded hepatic and peripheral endothelial cells in the New Zealand white rabbit.
PubMed:Oxidative alterations in the experimental glycation model of diabetes mellitus are due to protein-glucose adduct oxidation. Some fundamental differences in proposed mechanisms of glucose oxidation and oxidant production.
PubMed:Identification of core aldehydes among in vitro peroxidation products of cholesteryl esters.
PubMed:Flow cytometric measurement of ceroid accumulation in macrophages.
PubMed:Evaluation of oxidized low-density lipoprotein and large molecular size low-density lipoproteins in atherosclerosis.
PubMed:Ascorbic acid oxidation: a potential cause of the elevated severity of atherosclerosis in diabetes mellitus?
PubMed:An interaction between the human cholesteryl ester transfer protein (CETP) and apolipoprotein A-I genes in transgenic mice results in a profound CETP-mediated depression of high density lipoprotein cholesterol levels.
PubMed:Identification of cholesterol-bound aldehydes in copper-oxidized low density lipoprotein.
PubMed:Biosynthesis of cholesterol linoleate by polyethylene glycol-modified cholesterol esterase in organic solvents.
PubMed:Malondialdehyde modification and copper-induced autooxidation of high-density lipoprotein decrease cholesterol efflux from human cultured fibroblasts.
PubMed:Effect of conditioning of beta-migrating very low-density lipoprotein with macrophages on the accumulation of cholesteryl esters in smooth muscle cells.
PubMed:Serum cholesterol, cholesteryl ester, and high-density lipoprotein development in newborn infants: response to formulas supplemented with cholesterol and gamma-linolenic acid.
PubMed:Cellular damage in mouse peritoneal macrophages exposed to cholesteryl linoleate.
PubMed:Oxygen radicals and atherosclerosis.
PubMed:Use of radiation suicide to isolate constitutive and temperature-sensitive conditional Chinese hamster ovary cell mutants with defects in the endocytosis of low density lipoprotein.
PubMed:Lipid hydroperoxide involvement in copper-dependent and independent oxidation of low density lipoproteins.
PubMed:In vivo effect of simvastatin on lipoprotein cholesteryl ester metabolism in normocholesterolemic volunteers.
PubMed:Familial cholesteryl ester transfer protein deficiency is associated with triglyceride-rich low density lipoproteins containing cholesteryl esters of probable intracellular origin.
PubMed:Ceroid accumulation by murine peritoneal macrophages exposed to artificial lipid-containing particles: the role of the hydrophilic component.
PubMed:Growth-related modulation of human skin fibroblast cholesterol distribution and metabolism.
PubMed:Eutectic interactions between saturated and unsaturated chain cholesteryl esters: comparison of calculated and observed phase diagrams.
PubMed:Binary phase behavior of cholesteryl oleate with cholesteryl linoleate.
PubMed:Effects of oxidatively modified LDL on cholesterol esterification in cultured macrophages.
PubMed:Oxidation of cholesteryl linoleate by human monocyte-macrophages in vitro.
PubMed:Impaired plasma cholesteryl ester transfer with accumulation of larger high density lipoproteins in some families of baboons (Papio sp.).
PubMed:High-density-lipoprotein-induced cholesterol efflux from arterial smooth muscle cell derived foam cells: functional relationship of the cholesteryl ester cycle and eicosanoid biosynthesis.
PubMed:Lecithin-cholesterol acyltransferase (LCAT) catalyzes transacylation of intact cholesteryl esters. Evidence for the partial reversal of the forward LCAT reaction.
PubMed:Differential regulation of low density lipoprotein suppression of HMG-CoA reductase activity in cultured cells by inhibitors of cholesterol biosynthesis.
PubMed:Rapid intracellular transport of LDL-derived cholesterol to the plasma membrane in cultured fibroblasts.
PubMed:Presence of cholesteryl ester hydroperoxide in human blood plasma.
PubMed:Serum lipoprotein and Trypanosoma brucei brucei interactions in vitro.
PubMed:Metabolism of acetylated low density lipoproteins by monocyte-derived macrophages from patients with Werner's syndrome.
PubMed:Cholesteryl oleyl and linoleyl ethers do not trace their ester counterparts in animals with plasma cholesteryl ester transfer activity.
PubMed:Cholesterol flux between high density lipoproteins and cultured rat luteal cells.
PubMed:Neutral lipid accumulation in macrophages during lipid-induced macrophage growth.
PubMed:Modulation of ceroid accumulation in macrophages in vitro.
PubMed:Toxicity of rac-1(3)-myristoyl glycerol to mice.
PubMed:Phenothiazines inhibit cholesteryl ester formation in J 774 monocyte-like cells.
PubMed:Follicle-stimulating hormone regulates low density lipoprotein metabolism by swine granulosa cells.
PubMed:Differential uptake and metabolism of free and esterified cholesterol from high-density lipoproteins in the ovary.
PubMed:Fatty acid specificity of the lysosomal acid cholesterol esterase in intact human arterial smooth muscle cells.
PubMed:Ceroid accumulation by murine peritoneal macrophages exposed to artificial lipoproteins: ultrastructural observations.
PubMed:Effect of a new synthetic 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor on cholesterol synthesis and low density lipoprotein uptake by primary cultures of rat hepatocytes.
PubMed:The result of feeding palmitoyl glycerol on lymph and plasma lipids.
PubMed:Effects of substrate composition on the esterification and hydrolysis activity of lysosomal acid sterol ester hydrolase.
PubMed:The transfer of lipids from protein-free lipoprotein models to human fibroblasts in culture.
PubMed:The insulin-like growth factor, somatomedin-C, modulates low density lipoprotein metabolism by swine granulosa cells.
PubMed:Mechanisms subserving the steroidogenic synergism between follicle-stimulating hormone and insulin-like growth factor I (somatomedin C). Alterations in cellular sterol metabolism in swine granulosa cells.
PubMed:Ceroid accumulation by murine peritoneal macrophages exposed to artificial lipoproteins.
PubMed:Effect of fish oil versus lard diets on the chemical and physical properties of low density lipoproteins of nonhuman primates.
PubMed:Insulin regulates low density lipoprotein metabolism by swine granulosa cells.
PubMed:Specificity of lipid transfer protein for molecular species of cholesteryl ester.
PubMed:Molecular motions and thermotropic phase behavior of cholesteryl esters with triolein.
PubMed:[Effect of protein-vitamin deficiency on the enzyme activity of lipolysis and the synthesis of cholesterol esters during hypokinesia].
PubMed:Are plasma lipoprotein cholesteryl esters utilized for biliary cholesterol and bile acid production in man?
PubMed:Putative role of cholesteryl ester transfer protein in removal of cholesteryl ester from vascular interstitium, studied in a model system in cell culture.
PubMed:Incorporation in vitro of 14C fatty acids into bovine sebaceous gland and dermal lipids.
PubMed:Uptake of gold- and [3H]cholesteryl linoleate-labeled human low density lipoprotein by cultured rat granulosa cells: cellular mechanisms involved in lipoprotein metabolism and their importance to steroidogenesis.
PubMed:An alternative procedure for incorporating radiolabelled cholesteryl ester into human plasma lipoproteins in vitro.
PubMed:Verapamil enhances receptor-mediated endocytosis of low density lipoproteins by aortic cells in culture.
PubMed:Cholesterol ester and triglyceride metabolism in intact fibroblasts from patients with Wolman's disease and cholesterol ester storage disease.
PubMed:Thermotropic properties and molecular dynamics of cholesteryl ester rich very low density lipoproteins: effect of hydrophobic core on polar surface.
PubMed:[Serum cholesterol ester level in patients with ischemic heart disease and liver disease].
PubMed:Biosynthesis of bufadienolides in toads. V. The origin of the cholesterol used by toad parotid glands for biosynthesis of bufadienolides.
PubMed:Stimulation of progesterone synthesis in luteinized human granulosa cells by human chorionic gonadotropin and 8-bromo-adenosine 3',5'-monophosphate: the effect of low density lipoprotein.
PubMed:Human low density lipoproteins (LDL) in combination with cholesterol or cholesteryl linoleate as precursors for progesterone synthesis of human placenta in organ culture.
PubMed:The low-density lipoprotein pathway of cultured Leydig tumor cells. Utilization of low-density lipoprotein-derived cholesterol for steroidogenesis.
PubMed:Gas-liquid chromatographic determination of fatty acid composition of cholesteryl esters in human serum using silica Sep-Pak cartridges.
PubMed:Uptake of lipoproteins by in situ perfused rat ovaries: identification of binding sites for high density lipoproteins.
PubMed:Metabolism of HDL-cholesteryl ester in the rat, studied with a nonhydrolyzable analog, cholesteryl linoleyl ether.
PubMed:Conformation and packing of unsaturated chains in cholesteryl linolelaidate at 123 K.
PubMed:Binding, degradation, and utilization of plasma high density and low density lipoproteins for progesterone production in cultured rat luteal cells.
PubMed:Transfer of cholesteryl linoleyl ether from phosphatidylcholine and phosphatidylethanolamine liposomes to cultured cells catalyzed by lipoprotein lipase.
PubMed:Influence of human lipoproteins on the progesterone synthesis of human term placenta in organ culture.
PubMed:Temperature-dependent molecular motions of cholesterol esters: a carbon-13 nuclear magnetic resonance study.
PubMed:Concentration and composition of lipoproteins in blood plasma of the WHHL rabbit. An animal model of human familial hypercholesterolemia.
PubMed:Preparation of high-density lipoproteins labelled exclusively at the cholesteryl ester moiety.
PubMed:Anisotropic motion of the steroid ring system of cholesteryl esters. Calculation of carbon-13 nuclear magnetic resonance relaxation times and nuclear Overhauser enhancements and comparison with experiment.
PubMed:[Interrelation of the changes in the lipid composition of the blood serum and of subcellular liver fractions as affected by an atherogenic diet].
PubMed:Assessing methods for measuring compliance with a fat-controlled diet.
PubMed:Prostaglandin formation in man during intake of different amounts of linoleic acid in formula diets.
PubMed:Role of lipoprotein lipase in the uptake of cholesteryl ester by rat lactating mammary gland in vivo.
PubMed:Receptor-mediated gonadotropin action in the ovary. Demonstration of acute dependence of rat luteal cells on exogenously supplied steroid precursor (sterols) for gonadotropin-induced steroidogenesis.
PubMed:The mobility of cholesteryl esters in native and reconstituted low density lipoprotein as monitored by nuclear magnetic resonance spectroscopy.
PubMed:Stimulation of cholesteryl ester synthesis in macrophages by extracts of atherosclerotic human aortas and complexes of albumin/cholesteryl esters.
PubMed:In vivo uptake and metabolism of low density lipoprotein in the guinea pig adrenal.
PubMed:Brachymeria lasus and Pachycrepoideus vindemiae: sterol requirements during larval growth of two hymenopterous insect parasites reared in vitro on chemically defined media.
PubMed:Dietary ethanol-induced modifications in hyperlipoproteinemia and atherosclerosis in nonhuman primates (Macaca nemestrina).
PubMed:The fate of cholesteryl linoleyl ether and cholesteryl linoleate in the intact rat after injection of biologically labeled human low density lipoprotein.
PubMed:Effect of cigarette smoke and dietary cholesterol on plasma lipoprotein composition.
PubMed:Lecithin:cholesterol acyltransferase and serum fatty acids.
PubMed:Biological labeling of very low density lipoproteins with cholesteryl linoleyl ether and its fate in the intact rat.
PubMed:beta-Carotene as a probe of lipid domains of reconstituted human plasma low-density lipoprotein: induced circular dichroism.
PubMed:Prevention of coronary heart disease: the role of essential fatty acids.
PubMed:Influence of adrenocorticotropin on transport of a cholesteryl linoleate-low density lipoprotein complex into adrenal tumor cells.
PubMed:Reversible accumulation of cholesteryl esters in macrophages incubated with acetylated lipoproteins.
PubMed:Low density lipoprotein receptors in bovine adrenal cortex. I. Receptor-mediated uptake of low density lipoprotein and utilization of its cholesterol for steroid synthesis in cultured adrenocortical cells.
PubMed:Replacement of endogenous cholesteryl esters of low density lipoprotein with exogenous cholesteryl linoleate. Reconstitution of a biologically active lipoprotein particle.
PubMed:Lipid abnormalities in hereditary neuropathy. Part 2. Serum phospholipids.
PubMed:Effect of substrate composition and concentration on aortic cholesterol ester hydrolase activity.
PubMed:Cholesterol esters and membrane permeability. A nuclear magnetic resonance (MNR) study.
PubMed:Effect of an aqueous phase on the solubility of cholesterol in an oil phase.
PubMed:Fat emulsions with added free cholesterol or fatty acid cholesteryl esters. Studies on removal mechanisms in vivo and hydrolysis by lipoprotein lipase in vitro.
PubMed:Physical chemistry of the lipids of human atherosclerotic lesions. Demonstration of a lesion intermediate between fatty streaks and advanced plaques.
PubMed:Synthesis of cholesterol esters in the plasma and liver of sheep.
PubMed:Effects of palm-kernel oil and sunflower-seed oil on serum lipids and atherogenesis in alloxan-diabetic rabbits.
PubMed:Receptor-dependent hydrolysis of cholesteryl esters contained in plasma low density lipoprotein.
PubMed:Purification and properties of aortic cholesteryl ester hydrolase.
PubMed:Steroid balance and tissue cholesterol accumulation in germfree and conventional rats fed diets containing saturated and polyunsaturated fats.
PubMed:Lipids of human atheroma. 8. Oxidised derivatives of cholesteryl linoleate.
PubMed:Cholesterol metabolism in the macrophage. 3. Ingestion and intracellular fate of cholesterol and cholesterol esters.
PubMed:Phosphatidylcholine-cholesterol acyltransferase in the ultracentrifugal residual protein fraction of rat plasma.
PubMed:Properties of cholesteryl esters in pure and mixed monolayers.
PubMed:Further studies on platelet adhesiveness and serum cholesteryl linoleate levels in multiple sclerosis.
PubMed:Lipid composition of the vascular system during infancy, childhood, and young adulthood.
PubMed:Hydrolysis of cholesteryl linoleate by a high-speed supernatant preparation of rat and monkey aorta.
PubMed:Influence of diet on the composition of plasma cholesterol esters in man.
 
Notes:
Cholesteryl linoleic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl linoleate is contained in low density lipoprotein and atherosclerotic lesions. The oxidation products of cholesteryl linoleate may cause chronic inflammatory processes. (PMID 9684755, 11950694) [HMDB]
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