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18427-44-6,MFCD00919187
Catalog No.:AA00AQ7A

18427-44-6 | 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00AQ7A
Chemical Name:
9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID
CAS Number:
18427-44-6
Molecular Formula:
C18H28O2
Molecular Weight:
276.4137
MDL Number:
MFCD00919187
SMILES:
CC/C=C\C=C/C=C\C=C\CCCCCCCC(=O)O
Properties
Computed Properties
 
Complexity:
335  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
12  
Undefined Bond Stereocenter Count:
4  
XLogP3:
5.9  

Literature

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Title: TGF-β(2)- and H(2)O(2)-induced biological changes in optic nerve head astrocytes are reduced by the antioxidant alpha-lipoic acid.

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Title: Construction of a DOPC/PSM/cholesterol phase diagram based on the fluorescence properties of trans-parinaric acid.

Journal: Langmuir : the ACS journal of surfaces and colloids 20110705

Title: Parinaric acid methyl ester polymer films with hill-structured features: fabrication and different sensitivities to normal and tumor cells.

Journal: ACS applied materials & interfaces 20110701

Title: Using zeta-potential measurements to quantify peptide partition to lipid membranes.

Journal: European biophysics journal : EBJ 20110401

Title: Gel domains in the plasma membrane of Saccharomyces cerevisiae: highly ordered, ergosterol-free, and sphingolipid-enriched lipid rafts.

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Title: [Role of endogenous porphyrins in the effects of low-intensity laser radiation of the red region on free radical processes in the blood of rats under experimental endotoxic shock].

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Title: Cancer chemopreventive ability of conjugated linolenic acids.

Journal: International journal of molecular sciences 20110101

Title: MR imaging depicts oxidative stress induced by methemoglobin.

Journal: Radiology 20101101

Title: Ligand-enhanced expression and in-cell assay of human peroxisome proliferator-activated receptor alpha ligand binding domain.

Journal: Protein expression and purification 20100401

Title: The nonsteroidal anti-inflammatory drug indomethacin induces heterogeneity in lipid membranes: potential implication for its diverse biological action.

Journal: PloS one 20100101

Title: Differential ability of cholesterol-enriched and gel phase domains to resist benzyl alcohol-induced fluidization in multilamellar lipid vesicles.

Journal: Biochimica et biophysica acta 20091101

Title: Steady-state and time-resolved fluorescence studies of stripped Borage oil.

Journal: Analytica chimica acta 20090730

Title: Matrix metalloproteinase inhibitors (MMPIs) from marine natural products: the current situation and future prospects.

Journal: Marine drugs 20090601

Title: Combined bezafibrate and medroxyprogesterone acetate: potential novel therapy for acute myeloid leukaemia.

Journal: PloS one 20090101

Title: Cytotoxicity of unsaturated fatty acids in fresh human tumor explants: concentration thresholds and implications for clinical efficacy.

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Title: Diphenyl diselenide, a simple glutathione peroxidase mimetic, inhibits human LDL oxidation in vitro.

Journal: Atherosclerosis 20081101

Title: Contribution of culture media to oxidative stress and its effect on human oocytes.

Journal: Reproductive biomedicine online 20081101

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Title: Measuring the adsorption of Fatty acids to phospholipid vesicles by multiple fluorescence probes.

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Title: Combination of doxorubicin and low-intensity ultrasound causes a synergistic enhancement in cell killing and an additive enhancement in apoptosis induction in human lymphoma U937 cells.

Journal: Cancer chemotherapy and pharmacology 20080401

Title: Structural and functional characterization of a new recombinant histidine-tagged acyl coenzyme A binding protein (ACBP) from mouse.

Journal: Protein expression and purification 20080401

Title: N-palmitoyl-sulfatide participates in lateral domain formation in complex lipid bilayers.

Journal: Biochimica et biophysica acta 20080401

Title: Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism.

Journal: British journal of pharmacology 20071101

Title: Neuroleptic treatment effect on mitochondrial electron transport chain: peripheral blood mononuclear cells analysis in psychotic patients.

Journal: Journal of clinical psychopharmacology 20070601

Title: Fluorescence study of the fluidity and cooperativity of the phase transitions of zwitterionic and anionic liposomes confined in sol-gel glasses.

Journal: The journal of physical chemistry. B 20070412

Title: Impairments of the biological properties of serum albumin in patients on haemodialysis.

Journal: Nephrology (Carlton, Vic.) 20070201

Title: Cis-parinaric acid effects, cytotoxicity, c-Jun N-terminal protein kinase, forkhead transcription factor and Mn-SOD differentially in malignant and normal astrocytes.

Journal: Neurochemical research 20070101

Title: A simple method to differentiate between Mycobacterium tuberculosis and non-tuberculous mycobacteria directly on clinical specimens.

Journal: The Southeast Asian journal of tropical medicine and public health 20070101

Title: Fluorescence assays for measuring fatty acid binding and transport through membranes.

Journal: Methods in molecular biology (Clifton, N.J.) 20070101

Title: A yeast sterol carrier protein with fatty-acid and fatty-acyl-CoA binding activity.

Journal: Archives of biochemistry and biophysics 20060915

Title: Effect of anti-tumor ether lipids on ordered domains in model membranes.

Journal: FEBS letters 20060501

Title: Fatty acid transport and metabolism in HepG2 cells.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20060301

Title: Localization of a portion of the liver isoform of fatty-acid-binding protein (L-FABP) to peroxisomes.

Journal: The Biochemical journal 20060301

Title: Probing the influence of cis-trans isomers on model lipid membrane fluidity using cis-parinaric acid and a stop-flow technique.

Journal: Chemical communications (Cambridge, England) 20060207

Title: Comparison of phosphatidylcholine vesicle properties related to geometrical isomerism.

Journal: Photochemistry and photobiology 20060101

Title: trans-Parinaric acid as a versatile spectroscopic label to study ligand binding properties of bovine beta-lactoglobulin.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051101

Title: Isolation and structure determination of algicidal compounds from Ulva fasciata.

Journal: Bioscience, biotechnology, and biochemistry 20051101

Title: Delta98delta, a functional all-beta-sheet abridged form of intestinal fatty acid binding protein.

Journal: Biochemistry 20051025

Title: Displacement of sterols from sterol/sphingomyelin domains in fluid bilayer membranes by competing molecules.

Journal: Biochimica et biophysica acta 20050915

Title: The presence of molecular markers of in vivo lipid peroxidation in osteoarthritic cartilage: a pathogenic role in osteoarthritis.

Journal: Arthritis and rheumatism 20050901

Title: Peroxisome proliferator-activated receptor alpha interacts with high affinity and is conformationally responsive to endogenous ligands.

Journal: The Journal of biological chemistry 20050513

Title: Role of regulatory F-domain in hepatocyte nuclear factor-4alpha ligand specificity.

Journal: The Journal of biological chemistry 20050429

Title: Mitochondrial respiratory chain in brain homogenates: activities in different brain areas in patients with Alzheimer's disease.

Journal: Aging clinical and experimental research 20050201

Title: Quantification of selective phosphatidylserine oxidation during apoptosis.

Journal: Methods in molecular biology (Clifton, N.J.) 20050101

Title: Brilliant lipids.

Journal: Nature methods 20050101

Title: Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells.

Journal: The Journal of nutritional biochemistry 20041201

Title: Structure and cholesterol domain dynamics of an enriched caveolae/raft isolate.

Journal: The Biochemical journal 20040901

Title: Synthesis of four isomers of parinaric acid.

Journal: Chemistry and physics of lipids 20040901

Title: Membrane properties of plant sterols in phospholipid bilayers as determined by differential scanning calorimetry, resonance energy transfer and detergent-induced solubilization.

Journal: Biochimica et biophysica acta 20040830

Title: FT-Raman spectroscopy, fluorescent probe, and solvent accessibility study of egg and milk proteins.

Journal: Journal of agricultural and food chemistry 20040811

Title: The plasma membrane is the site of selective phosphatidylserine oxidation during apoptosis: role of cytochrome C.

Journal: Antioxidants & redox signaling 20040401

Title: Vitamin E inhibits anti-Fas-induced phosphatidylserine oxidation but does not affect its externalization during apoptosis in Jurkat T cells and their phagocytosis by J774A.1 macrophages.

Journal: Antioxidants & redox signaling 20040401

Title: [Ex vivo analysis of mitochondrial function in patients attended in an emergency department due to carbon monoxide poisoning].

Journal: Medicina clinica 20040327

Title: Attenuation of lipid peroxidation by antioxidants in rat-1 fibroblasts: comparison of the lipid peroxidation reporter molecules cis-parinaric acid and C11-BODIPY(581/591) in a biological setting.

Journal: Biochimica et biophysica acta 20040322

Title: Liver fatty acid-binding protein colocalizes with peroxisome proliferator activated receptor alpha and enhances ligand distribution to nuclei of living cells.

Journal: Biochemistry 20040309

Title: Mitochondrial effects of antiretroviral therapies in asymptomatic patients.

Journal: Antiviral therapy 20040201

Title: Binding analyses between Human PPARgamma-LBD and ligands.

Journal: European journal of biochemistry 20040101

Title: Conjugated docosahexaenoic acid suppresses KPL-1 human breast cancer cell growth in vitro and in vivo: potential mechanisms of action.

Journal: Breast cancer research : BCR 20040101

Title: Antioxidant protection of low density lipoprotein by procyanidins: structure/activity relationships.

Journal: Biochemical pharmacology 20030915

Title: Structural and biochemical characterization of toad liver fatty acid-binding protein.

Journal: Biochemistry 20030715

Title: Intrinsic tyrosine fluorescence as a tool to study the interaction of the shaker B 'ball' peptide with anionic membranes.

Journal: Biochemistry 20030617

Title: Decreased liver fatty acid binding capacity and altered liver lipid distribution in mice lacking the liver fatty acid-binding protein gene.

Journal: The Journal of biological chemistry 20030613

Title: Ascorbic acid spares alpha-tocopherol and prevents lipid peroxidation in cultured H4IIE liver cells.

Journal: Molecular and cellular biochemistry 20030501

Title: The cell membrane as a biosensor of oxidative stress induced by radiation exposure: a multiparameter investigation.

Journal: Radiation research 20030401

Title: The FAR protein family of the nematode Caenorhabditis elegans. Differential lipid binding properties, structural characteristics, and developmental regulation.

Journal: The Journal of biological chemistry 20030307

Title: Electrospray mass spectrometric investigation of the binding of cis-parinaric acid to bovine beta-lactoglobulin and study of the ligand-binding site of the protein using limited proteolysis.

Journal: Rapid communications in mass spectrometry : RCM 20030101

Title: Role of beer lipid-binding proteins in preventing lipid destabilization of foam.

Journal: Journal of agricultural and food chemistry 20021218

Title: Bax-induced cell death in yeast depends on mitochondrial lipid oxidation.

Journal: European journal of biochemistry 20021101

Title: Surface fluorescence resonance energy transfer studies on interfacial adsorption of Thermomyces (humicola) lanuginosa lipase, using monomolecular films of cis-parinaric acid.

Journal: Biopolymers 20021015

Title: Segregation of phosphatidic acid-rich domains in reconstituted acetylcholine receptor membranes.

Journal: Biochemistry 20021008

Title: The CYP4A isoforms hydroxylate epoxyeicosatrienoic acids to form high affinity peroxisome proliferator-activated receptor ligands.

Journal: The Journal of biological chemistry 20020920

Title: Hydrophobic probe binding of beta-lactoglobulin in the native and molten globule state induced by high pressure as affected by pH, KIO(3) and N-ethylmaleimide.

Journal: Journal of agricultural and food chemistry 20020828

Title: Liver fatty acid-binding protein targets fatty acids to the nucleus. Real time confocal and multiphoton fluorescence imaging in living cells.

Journal: The Journal of biological chemistry 20020809

Title: Anti-/pro-oxidant effects of phenolic compounds in cells: are colchicine metabolites chain-breaking antioxidants?

Journal: Toxicology 20020801

Title: Induced chirality upon binding of cis-parinaric acid to bovine beta-lactoglobulin: spectroscopic characterization of the complex.

Journal: FEBS letters 20020605

Title: Modification of fatty acid composition in tomato (Lycopersicon esculentum) by expression of a borage delta6-desaturase.

Journal: Molecular biotechnology 20020601

Title: Selective peroxidation and externalization of phosphatidylserine in normal human epidermal keratinocytes during oxidative stress induced by cumene hydroperoxide.

Journal: The Journal of investigative dermatology 20020601

Title: Binding of Thermomyces (Humicola) lanuginosa lipase to the mixed micelles of cis-parinaric acid/NaTDC.

Journal: European journal of biochemistry 20020301

Title: Nonequilibrium phenomena in the phase separation of a two-component lipid bilayer.

Journal: Biophysical journal 20020201

Title: Diclofenac antagonizes peroxisome proliferator-activated receptor-gamma signaling.

Journal: Molecular pharmacology 20020101

Title: Antioxidant protection of propofol and its recycling in erythrocyte membranes.

Journal: American journal of respiratory and critical care medicine 20020101

Title: Evaluation of hydrophobicity versus chaperonelike activity of bovine alphaA- and alphaB-crystallin.

Journal: Journal of protein chemistry 20020101

Title: Depletion of Bcl-2 by an antisense oligonucleotide induces apoptosis accompanied by oxidation and externalization of phosphatidylserine in NCI-H226 lung carcinoma cells.

Journal: Molecular and cellular biochemistry 20020101

Title: Fluorescence-based ligand-binding assays for peroxisome proliferator-activated receptors.

Journal: Methods in enzymology 20020101

Title: Protein-lipid interactions in reconstituted high density lipoproteins: apolipoprotein and cholesterol influence.

Journal: Chemistry and physics of lipids 20011101

Title: Binding properties of Echinococcus granulosus fatty acid binding protein.

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Title: Interaction of chicken liver basic fatty acid-binding protein with fatty acids: a 13C NMR and fluorescence study.

Journal: Biochemistry 20011023

Title: Hydrophobicity of whey protein concentrates measured by fluorescence quenching and its relation with surface functional properties.

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Title: Manganese superoxide dismutase-plasmid/liposome (MnSOD-PL) administration protects mice from esophagitis associated with fractionated radiation.

Journal: International journal of cancer 20010820

Title: Pressure-induced denaturation of monomer beta-lactoglobulin is partially irreversible: comparison of monomer form (highly acidic pH) with dimer form (neutral pH).

Journal: Journal of agricultural and food chemistry 20010801

Title: Mechanisms by which intracellular calcium induces susceptibility to secretory phospholipase A2 in human erythrocytes.

Journal: The Journal of biological chemistry 20010622

Title: Uterocalin, a lipocalin provisioning the preattachment equine conceptus: fatty acid and retinol binding properties, and structural characterization.

Journal: The Biochemical journal 20010601

Title: A surface-associated retinol- and fatty acid-binding protein (Gp-FAR-1) from the potato cyst nematode Globodera pallida: lipid binding activities, structural analysis and expression pattern.

Journal: The Biochemical journal 20010601

Title: Enhanced oxidative susceptibility and reduced antioxidant content of metabolic precursors of small, dense low-density lipoproteins.

Journal: The American journal of medicine 20010201

Title: Quantitative analysis of phospholipid peroxidation and antioxidant protection in live human epidermal keratinocytes.

Journal: Bioscience reports 20010201

Title: Cryopreservation in different concentrations of glycerol alters boar sperm and their membranes.

Journal: Journal of andrology 20010101

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Tags:18427-44-6 Molecular Formula|18427-44-6 MDL|18427-44-6 SMILES|18427-44-6 9Z,11E,13E,15Z-OCTADECATETRAENOIC ACID