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23017-93-8
Catalog No.:AA002LSY

23017-93-8 | 9,11-Octadecadienoic acid, 13-hydroperoxy-, (9Z,11E)-

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002LSY
Chemical Name:
9,11-Octadecadienoic acid, 13-hydroperoxy-, (9Z,11E)-
CAS Number:
23017-93-8
Molecular Formula:
C18H32O4
Molecular Weight:
312.4443
SMILES:
CCCCCC(/C=C/C=C\CCCCCCCC(=O)O)OO
Properties
Computed Properties
 
Complexity:
310  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
15  
Undefined Atom Stereocenter Count:
1  
XLogP3:
5.4  

Literature

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Journal: Journal of clinical biochemistry and nutrition 20160501

Title: Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Molecular cloning and identification of divinyl ether synthases CYP74M1 and CYP74M3.

Journal: Biochimica et biophysica acta 20160401

Title: Angiotensin II modification by decomposition products of linoleic acid-derived lipid hydroperoxide.

Journal: Chemico-biological interactions 20150905

Title: Atherogenic ω-6 Lipids Modulate PPAR- EGR-1 Crosstalk in Vascular Cells.

Journal: PPAR research 20110101

Title: Identification of a lipid peroxidation product as the source of oxidation-specific epitopes recognized by anti-DNA autoantibodies.

Journal: The Journal of biological chemistry 20101029

Title: L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice.

Journal: Drug metabolism letters 20100801

Title: Proteins modified by the lipid peroxidation aldehyde 9,12-dioxo-10(E)-dodecenoic acid in MCF7 breast cancer cells.

Journal: Chemical research in toxicology 20100315

Title: Increased lipid peroxidation in Down's syndrome mouse models.

Journal: Journal of neurochemistry 20090901

Title: Mechanistic investigations of human reticulocyte 15- and platelet 12-lipoxygenases with arachidonic acid.

Journal: Biochemistry 20090707

Title: Alpha-tocopherol is ineffective in preventing the decomposition of preformed lipid peroxides and may promote the accumulation of toxic aldehydes: a potential explanation for the failure of antioxidants to affect human atherosclerosis.

Journal: Antioxidants & redox signaling 20090601

Title: Sialic acid attenuates the cytotoxicity of the lipid hydroperoxides HpODE and HpETE.

Journal: Carbohydrate research 20090512

Title: Induction of adaptive response and enhancement of PC12 cell tolerance by lipopolysaccharide primarily through the upregulation of glutathione S-transferase A3 via Nrf2 activation.

Journal: Free radical biology & medicine 20081115

Title: Substrate specificity changes for human reticulocyte and epithelial 15-lipoxygenases reveal allosteric product regulation.

Journal: Biochemistry 20080715

Title: Lipoxygenase distribution in coffee (Coffea arabica L.) berries.

Journal: Journal of agricultural and food chemistry 20071003

Title: Covalent adducts arising from the decomposition products of lipid hydroperoxides in the presence of cytochrome c.

Journal: Chemical research in toxicology 20070501

Title: Research paper effects of 13-HPODE on expression of genes involved in thyroid hormone synthesis, iodide uptake and formation of hydrogen peroxide in porcine thyrocytes.

Journal: International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20061101

Title: Effect of a conjugated quercetin metabolite, quercetin 3-glucuronide, on lipid hydroperoxide-dependent formation of reactive oxygen species in differentiated PC-12 cells.

Journal: Free radical research 20061001

Title: Metabolism of oxidized linoleic acid by glutathione transferases: peroxidase activity toward 13-hydroperoxyoctadecadienoic acid.

Journal: Biochimica et biophysica acta 20060701

Title: Apolipoprotein A-I-mimetic peptides with antioxidant actions.

Journal: Archives of biochemistry and biophysics 20060701

Title: Differential action of 13-HPODE on PPARalpha downstream genes in rat Fao and human HepG2 hepatoma cell lines.

Journal: The Journal of nutritional biochemistry 20060601

Title: The regulation of formation of prostaglandins and arachidonoyl-CoA from arachidonic acid in rabbit kidney medulla microsomes by linoleic acid hydroperoxide.

Journal: Prostaglandins & other lipid mediators 20060501

Title: Activation of AP-1 and increased synthesis of MMP-9 in the rabbit retina induced by lipid hydroperoxide.

Journal: Current eye research 20060401

Title: Enhancement by cigarette smoke extract of the radical formation in a reaction mixture of 13-hydroperoxide octadecadienoic acid and ferric ions.

Journal: Journal of biochemistry 20060401

Title: Dependence on the phospholipid polyunsaturated fatty acids of the oxidative injury of isolated cardiomyocytes.

Journal: Free radical research 20060301

Title: Dual positional and stereospecificity of lipoxygenase isoenzymes from germinating barley (green malt): biotransformation of free and esterified linoleic acid.

Journal: Journal of agricultural and food chemistry 20060208

Title: Approach to novel functional foods for stress control 5. Antioxidant activity profiles of antidepressant herbs and their active components.

Journal: The journal of medical investigation : JMI 20051101

Title: Aspergillus infection inhibits the expression of peanut 13S-HPODE-forming seed lipoxygenases.

Journal: Molecular plant-microbe interactions : MPMI 20051001

Title: Kinetic properties of lipoxygenase from desert truffle (Terfezia claveryi Chatin) ascocarps: effect of inhibitors and activators.

Journal: Journal of agricultural and food chemistry 20050727

Title: Analysis of FeII-mediated decomposition of a linoleic acid-derived lipid hydroperoxide by liquid chromatography/mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20050501

Title: Dual role of oxygen during lipoxygenase reactions.

Journal: The FEBS journal 20050501

Title: Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and beta-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes.

Journal: Planta 20050401

Title: Glutathione peroxidase mimics as novel antioxidants from vegetables.

Journal: BioFactors (Oxford, England) 20050101

Title: The novel pathway for ketodiene oxylipin biosynthesis in Jerusalem artichoke (Helianthus tuberosus) tubers.

Journal: Biochimica et biophysica acta 20041108

Title: Tryptophan 500 and arginine 707 define product and substrate active site binding in soybean lipoxygenase-1.

Journal: Biochemistry 20041019

Title: The inhibitory effect of luteolin-7-O-glucoside on the formation of pentyl and 7-carboxyheptyl radicals from 13-hydroperoxy-9,11-octadecadienoic acid in the presence of iron(II) ions.

Journal: Free radical research 20040801

Title: Incorporation of arachidonic and linoleic acid hydroperoxides into cultured human umbilical vein endothelial cells.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20040601

Title: Regulation of monocyte chemoattractant protein-1 by the oxidized lipid, 13-hydroperoxyoctadecadienoic acid, in vascular smooth muscle cells via nuclear factor-kappa B (NF-kappa B).

Journal: Journal of molecular and cellular cardiology 20040401

Title: The C2-like beta-barrel domain mediates the Ca2+-dependent resistance of 5-lipoxygenase activity against inhibition by glutathione peroxidase-1.

Journal: The Journal of biological chemistry 20031031

Title: Kinetic studies of oxygen reactivity in soybean lipoxygenase-1.

Journal: Biochemistry 20031007

Title: A cis-acting region regulates oxidized lipid-mediated induction of the human heme oxygenase-1 gene in endothelial cells.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20030801

Title: The formation of the 7-carboxyheptyl radical from 13-hydroperoxy-9,11-octadecadienoic acid catalyzed by hemoglobin and myoglobin under anaerobic conditions.

Journal: Journal of biochemistry 20030501

Title: Activation of NAD(P)H oxidase by lipid hydroperoxides: mechanism of oxidant-mediated smooth muscle cytotoxicity.

Journal: Free radical biology & medicine 20030401

Title: Purification of lipoxygenase from Chlorella: production of 9- and 13-hydroperoxide derivatives of linoleic acid.

Journal: Lipids 20021101

Title: Irreversible inactivation of soybean lipoxygenase-1 by hydrophobic thiols.

Journal: Biochemistry 20020924

Title: Kinetics of inhibition of leukocyte 12-lipoxygenase by the isoform-specific inhibitor 4-(2-oxapentadeca-4-yne)phenylpropanoic acid.

Journal: Biochemistry 20020813

Title: Purification of hydroperoxide lyase from green bell pepper (Capsicum annuum L.) fruits for the generation of C6-aldehydes in vitro.

Journal: Journal of agricultural and food chemistry 20020327

Title: Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide.

Journal: The Biochemical journal 20020101

Title: Perturbation of lipid metabolism by linoleic acid hydroperoxide in CaCo-2 cells.

Journal: Biological chemistry 20020101

Title: 13(S)-HpODE modulates mitogenic signal transduction through enhancing the phosphorylation and association of EGF receptor with the tyrosine phosphatase SHP-2.

Journal: Advances in experimental medicine and biology 20020101

Title: Three-dimensional structure of a purple lipoxygenase.

Journal: Journal of the American Chemical Society 20011107

Title: Antioxidant activity of extracts from plants growing in Sardinia.

Journal: Phytotherapy research : PTR 20010901

Title: Signaling mechanisms of nuclear factor-kappab-mediated activation of inflammatory genes by 13-hydroperoxyoctadecadienoic acid in cultured vascular smooth muscle cells.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20010901

Title: The homolytic and heterolytic fatty acid hydroperoxide lyase-like activities of hematin.

Journal: Biochemical and biophysical research communications 20010810

Title: Cultivar-dependent expression of a maize lipoxygenase responsive to seed infesting fungi.

Journal: Molecular plant-microbe interactions : MPMI 20010801

Title: Characterization of lipoxygenase oxidation products by high-performance liquid chromatography with electron impact-mass spectrometric detection.

Journal: Lipids 20010801

Title: Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals.

Journal: The Journal of biological chemistry 20010615

Title: Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins.

Journal: Science (New York, N.Y.) 20010615

Title: Effect of 4-hydroxy-2(E)-nonenal on soybean lipoxygenase-1.

Journal: Lipids 20010601

Title: Aldehydic lipid peroxidation products derived from linoleic acid.

Journal: Biochimica et biophysica acta 20010430

Title: Mechanism of acetaminophen inhibition of cyclooxygenase isoforms.

Journal: Archives of biochemistry and biophysics 20010315

Title: 12-lipoxygenase in porcine coronary microcirculation: implications for coronary vasoregulation.

Journal: American journal of physiology. Heart and circulatory physiology 20010201

Title: Oxygenation of (3Z)-alkenals to 4-hydroxy-(2E)-alkenals in plant extracts: a nonenzymatic process.

Journal: Biochemical and biophysical research communications 20001014

Title: Lipid peroxides induce expression of catalase in cultured vascular cells.

Journal: Journal of lipid research 20000801

Title: Linoleyl hydroperoxide transcriptionally upregulates heme oxygenase-1 gene expression in human renal epithelial and aortic endothelial cells.

Journal: Journal of the American Society of Nephrology : JASN 19981101

Title: Divinyl ether synthase from garlic (Allium sativum L.) bulbs: sub-cellular localization and substrate regio-and stereospecificity.

Journal: FEBS letters 19960617

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Tags:23017-93-8 Molecular Formula|23017-93-8 MDL|23017-93-8 SMILES|23017-93-8 9,11-Octadecadienoic acid, 13-hydroperoxy-, (9Z,11E)-