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1191-85-1,MFCD00036967
Catalog No.:AA000I4N

1191-85-1 | 5,8,11,14-Eicosatetraynoic acid

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5mg
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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA000I4N
Chemical Name:
5,8,11,14-Eicosatetraynoic acid
CAS Number:
1191-85-1
Molecular Formula:
C20H24O2
Molecular Weight:
296.4034
MDL Number:
MFCD00036967
SMILES:
CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
Properties
Computed Properties
 
Complexity:
586  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
6  
XLogP3:
5.3  

Literature

Title: Enhanced NADPH oxidases and reactive oxygen species in the mechanism of methanol-initiated protein oxidation and embryopathies in vivo and in embryo culture.

Journal: Archives of toxicology 20160301

Title: Protective effects of arachidonic acid against palmitic acid-mediated lipotoxicity in HIT-T15 cells.

Journal: Molecular and cellular biochemistry 20120501

Title: Small-molecule inhibitors of biofilm formation in laboratory and clinical isolates of Candida albicans.

Journal: Journal of medical microbiology 20120101

Title: 5, 8, 11, 14-eicosatetraynoic acid suppresses CCL2/MCP-1 expression in IFN-γ-stimulated astrocytes by increasing MAPK phosphatase-1 mRNA stability.

Journal: Journal of neuroinflammation 20120101

Title: Arachidonic acid modulates Na+ currents by non-metabolic and metabolic pathways in rat cerebellar granule cells.

Journal: The Biochemical journal 20110815

Title: Embryopathic effects of thalidomide and its hydrolysis products in rabbit embryo culture: evidence for a prostaglandin H synthase (PHS)-dependent, reactive oxygen species (ROS)-mediated mechanism.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20110701

Title: High extracellular Ca2+ stimulates Ca2+-activated Cl- currents in frog parathyroid cells through the mediation of arachidonic acid cascade.

Journal: PloS one 20110101

Title: Peroxisome proliferator-activated receptor α and γ agonists together with TGF-β convert human CD4+CD25- T cells into functional Foxp3+ regulatory T cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20101215

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Effects of clodronate combined with hydroxyapatite on multi-directional differentiation of mesenchymal stromal cells.

Journal: Archives of medical science : AMS 20101001

Title: Abscisic acid-induced resistance against the brown spot pathogen Cochliobolus miyabeanus in rice involves MAP kinase-mediated repression of ethylene signaling.

Journal: Plant physiology 20100401

Title: Non-genomic effects of PPARgamma ligands: inhibition of GPVI-stimulated platelet activation.

Journal: Journal of thrombosis and haemostasis : JTH 20100301

Title: Riboflavin induces resistance in rice against Rhizoctonia solani via jasmonate-mediated priming of phenylpropanoid pathway.

Journal: Journal of plant physiology 20100215

Title: A reexamination of the PPAR-alpha activation mode of action as a basis for assessing human cancer risks of environmental contaminants.

Journal: Environmental health perspectives 20091101

Title: Arachidonic Acid Activates K-Cl-cotransport in HepG2 Human Hepatoblastoma Cells.

Journal: The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology 20091001

Title: Calcium-independent phospholipase A2 participates in KCl-induced calcium sensitization of vascular smooth muscle.

Journal: Cell calcium 20090701

Title: Modulation of muscle rNaV1.4 Na+ channel isoform by arachidonic acid and its non-metabolized analog.

Journal: Journal of cellular physiology 20090401

Title: Possible mediators of connecting tubule glomerular feedback.

Journal: Hypertension (Dallas, Tex. : 1979) 20090201

Title: Measurement of lipid hydroperoxides by the ferric-xylenol orange method (2) application to lipoxygenase assay.

Journal: Journal of nutritional science and vitaminology 20090201

Title: Imbalance of angiotensin type 1 receptor and angiotensin II type 2 receptor in the rostral ventrolateral medulla: potential mechanism for sympathetic overactivity in heart failure.

Journal: Hypertension (Dallas, Tex. : 1979) 20081001

Title: Potent in vitro antifungal activities of naturally occurring acetylenic acids.

Journal: Antimicrobial agents and chemotherapy 20080701

Title: Activation of TRPA1 by farnesyl thiosalicylic acid.

Journal: Molecular pharmacology 20080401

Title: The flavonoid quercetin regulates growth and gene expression in rat FRTL-5 thyroid cells.

Journal: Endocrinology 20080101

Title: A role for phospholipase A in auxin-regulated gene expression.

Journal: FEBS letters 20070904

Title: Flufenamic acid bi-directionally modulates the transient outward K(+) current in rat cerebellar granule cells.

Journal: The Journal of pharmacology and experimental therapeutics 20070701

Title: Expression and mechanism of spleen tyrosine kinase activation by angiotensin II and its implication in protein synthesis in rat vascular smooth muscle cells.

Journal: The Journal of biological chemistry 20070608

Title: Ligand-dependent transcriptional activities of four torafugu pufferfish Takifugu rubripes peroxisome proliferator-activated receptors.

Journal: General and comparative endocrinology 20070101

Title: Platelet-induced growth of human fibroblasts is associated with an increased expression of 5-lipoxygenase.

Journal: Thrombosis and haemostasis 20061101

Title: Arachidonic acid enhances intracellular [Ca2+]i increase and mitochondrial depolarization induced by glutamate in cerebellar granule cells.

Journal: Biochemistry. Biokhimiia 20060801

Title: Arachidonic acid is a physiological activator of the ryanodine receptor in pancreatic beta-cells.

Journal: Cell calcium 20060601

Title: Relationship between prostaglandin E2 and vascular endothelial growth factor (VEGF) in angiogenesis in human vascular endothelial cells.

Journal: Vascular pharmacology 20060601

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Feed forward cycle of hypotonic stress-induced ATP release, purinergic receptor activation, and growth stimulation of prostate cancer cells.

Journal: The Journal of biological chemistry 20060303

Title: The cysteinyl-leukotriene-1 receptor antagonist zafirlukast is a potent secretagogue in rat and human airways.

Journal: European journal of pharmacology 20051219

Title: Leukotrienes modulate cytokine release from dendritic cells.

Journal: Immunology 20051201

Title: {Omega}-3 and {omega}-6 polyunsaturated fatty acids block HERG channels.

Journal: American journal of physiology. Cell physiology 20051101

Title: Molecular targets of dietary polyphenols with anti-inflammatory properties.

Journal: Yonsei medical journal 20051031

Title: beta-Aminobutyric acid-induced resistance against downy mildew in grapevine acts through the potentiation of callose formation and jasmonic acid signaling.

Journal: Molecular plant-microbe interactions : MPMI 20050801

Title: PPAR-alpha activators suppress STAT1 inflammatory signaling in lipopolysaccharide-activated rat glia.

Journal: Neuroreport 20050531

Title: Structural stability of soybean lipoxygenase-1 in solution as probed by small angle X-ray scattering.

Journal: Journal of molecular biology 20050527

Title: Angiotensin II-induced Akt activation is mediated by metabolites of arachidonic acid generated by CaMKII-stimulated Ca2(+)-dependent phospholipase A2.

Journal: American journal of physiology. Heart and circulatory physiology 20050501

Title: Angiotensin II-induced Akt activation through the epidermal growth factor receptor in vascular smooth muscle cells is mediated by phospholipid metabolites derived by activation of phospholipase D.

Journal: The Journal of pharmacology and experimental therapeutics 20050301

Title: Capsazepine, a vanilloid antagonist, abolishes tonic responses induced by 20-HETE on guinea pig airway smooth muscle.

Journal: American journal of physiology. Lung cellular and molecular physiology 20050301

Title: Complex expression and localization of inactivating Kv channels in cultured hippocampal astrocytes.

Journal: Journal of neurophysiology 20050301

Title: NADPH oxidase produces reactive oxygen species and maintains survival of rat astrocytes.

Journal: Cell biochemistry and function 20050101

Title: Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.

Journal: The British journal of dermatology 20041001

Title: Lipoxygenase-dependent superoxide release in skeletal muscle.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20040801

Title: Identification and localization of an arachidonic acid-sensitive potassium channel in the cochlea.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040714

Title: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.

Journal: Neuron 20040325

Title: Ca2+ influx is not involved in acute cytotoxicity of arachidonic acid.

Journal: Biochemical pharmacology 20040301

Title: Decrease of human hepatoma cell growth by arachidonic acid is associated with an accumulation of derived products from lipid peroxidation.

Journal: Biochimie 20040101

Title: Reactive oxygen species mediate arachidonic acid-induced dilation in porcine coronary microvessels.

Journal: American journal of physiology. Heart and circulatory physiology 20031201

Title: Lipoxygenase inhibitors enhance tumor suppressive effects of jun proteins on v-myb-transformed monoblasts BM2.

Journal: Prostaglandins & other lipid mediators 20031101

Title: Inhibition by arachidonic acid and other fatty acids of dopamine uptake at the human dopamine transporter.

Journal: European journal of pharmacology 20031008

Title: Arachidonic acid regulates surface expression of epithelial sodium channels.

Journal: The Journal of biological chemistry 20030919

Title: Arachidonic acid activates a functional AP-1 and an inactive NF-kappaB complex in human HepG2 hepatoma cells.

Journal: Free radical biology & medicine 20030915

Title: Modulation of guinea pig intrinsic cardiac neurons by prostaglandins.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20030901

Title: Arachidonic acid in astrocytes blocks Ca(2+) oscillations by inhibiting store-operated Ca(2+) entry, and causes delayed Ca(2+) influx.

Journal: Cell calcium 20030401

Title: Creating conditions similar to those that occur during exposure of cells to microgravity induces apoptosis in human lymphocytes by 5-lipoxygenase-mediated mitochondrial uncoupling and cytochrome c release.

Journal: Journal of leukocyte biology 20030401

Title: Nitric oxide co-ordinates the activities of the capacitative and non-capacitative Ca2+-entry pathways regulated by vasopressin.

Journal: The Biochemical journal 20030301

Title: A role for TRPV1 in bradykinin-induced excitation of vagal airway afferent nerve terminals.

Journal: The Journal of pharmacology and experimental therapeutics 20030301

Title: Pyloric ceca are significant sites of newly synthesized 22:6n-3 in rainbow trout (Oncorhynchus mykiss).

Journal: Lipids 20030101

Title: PPARalpha inhibits TGF-beta-induced beta5 integrin transcription in vascular smooth muscle cells by interacting with Smad4.

Journal: Circulation research 20021129

Title: Angiotensin II constriction of rat vasa recta is partially thromboxane dependent.

Journal: Hypertension (Dallas, Tex. : 1979) 20021001

Title: Role of cytoplasmic phospholipase A2 in endothelium-derived hyperpolarizing factor dilations of rat middle cerebral arteries.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20021001

Title: Effects of arachidonic acid on sodium currents in rat dorsal root ganglion neurons.

Journal: Brain research 20020920

Title: Molecular identification of cytosolic, patatin-related phospholipases A from Arabidopsis with potential functions in plant signal transduction.

Journal: Plant physiology 20020901

Title: N-acylethanolamines are metabolized by lipoxygenase and amidohydrolase in competing pathways during cottonseed imbibition.

Journal: Plant physiology 20020901

Title: Arachidonic acid and docosahexaenoic acid suppress thrombin-evoked Ca2+ response in rat astrocytes by endogenous arachidonic acid liberation.

Journal: Journal of neurochemistry 20020901

Title: Pivotal role of superoxides generated in the mitochondrial respiratory chain in peroxynitrite-dependent activation of phospholipase A2.

Journal: The Biochemical journal 20020815

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

Journal: Biochemistry 20020813

Title: Exercise training increases membrane bound form of tumor necrosis factor-alpha receptors with decreases in the secretion of soluble forms of receptors in rat adipocytes.

Journal: Life sciences 20020621

Title: Contribution of renal oxygenases to glycerol-induced acute renal failure in the rat.

Journal: Journal of cardiovascular pharmacology 20020601

Title: Induction of MnSOD gene by arachidonic acid is mediated by reactive oxygen species and p38 MAPK signaling pathway in human HepG2 hepatoma cells.

Journal: Free radical biology & medicine 20020601

Title: Evaluation of lipopolysaccharide-induced activation of equine neutrophils.

Journal: American journal of veterinary research 20020601

Title: Arachidonic acid increases intracellular calcium in erythrocytes.

Journal: Biochemical and biophysical research communications 20020510

Title: Arachidonic acid differentially affects basal and lipopolysaccharide-induced sPLA(2)-IIA expression in alveolar macrophages through NF-kappaB and PPAR-gamma-dependent pathways.

Journal: Molecular pharmacology 20020401

Title: Effect of homocysteine on arachidonic acid release in human platelets.

Journal: European journal of clinical investigation 20020401

Title: Nitric oxide inactivation in brain by a novel O2-dependent mechanism resulting in the formation of nitrate ions.

Journal: The Biochemical journal 20020301

Title: Involvement of protein kinase C and arachidonic acid pathways in the gonadotropin-releasing hormone regulation of oocyte meiosis and follicular steroidogenesis in the goldfish ovary.

Journal: Biology of reproduction 20020301

Title: Multiple biological effects of inhibitors of arachidonic acid metabolism on human keratinocytes.

Journal: Archives of dermatological research 20020201

Title: Lipoxygenase inhibitors inhibit heparin-releasable lipoprotein lipase activity in 3T3-L1 adipocytes and enhance body fat reduction in mice by conjugated linoleic acid.

Journal: Biochimica et biophysica acta 20011130

Title: Calcium influx, arachidonic acid,and control of endothelial cell proliferation.

Journal: Cell calcium 20011001

Title: A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.

Journal: British journal of pharmacology 20010901

Title: Angiotensin II type AT(2) receptor mRNA expression and renal vasodilatation are increased in renal failure.

Journal: Hypertension (Dallas, Tex. : 1979) 20010901

Title: Contrasting effects of cPLA2 on epithelial Na+ transport.

Journal: American journal of physiology. Cell physiology 20010701

Title: Actions of arachidonic acid on contractions and associated electrical activity in guinea-pig isolated ventricular myocytes.

Journal: Experimental physiology 20010701

Title: Cloning of the human cholesteryl ester hydrolase promoter: identification of functional peroxisomal proliferator-activated receptor responsive elements.

Journal: Biochemical and biophysical research communications 20010622

Title: Kinetic modulation of Kv4-mediated A-current by arachidonic acid is dependent on potassium channel interacting proteins.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010615

Title: Arachidonic acid directly activates members of the mitogen-activated protein kinase superfamily in rabbit proximal tubule cells.

Journal: Kidney international 20010601

Title: Chronotropic effect of angiotensin II via type 2 receptors in rat brain neurons.

Journal: Journal of neurophysiology 20010501

Title: Eicosatetraynoic acid (ETYA), a non-metabolizable analogue of arachidonic acid, blocks the fast-inactivating potassium current of rat pituitary melanotrophs.

Journal: Canadian journal of physiology and pharmacology 20010401

Title: Triple-bonded unsaturated fatty acids are redox active compounds.

Journal: Lipids 20010401

Title: TNF-alpha inhibits 3T3-L1 adipocyte differentiation without downregulating the expression of C/EBPbeta and delta.

Journal: Endocrine journal 20010401

Title: Epoxyeicosatrienoic acid-mediated renal vasodilation to arachidonic acid is enhanced in SHR.

Journal: Hypertension (Dallas, Tex. : 1979) 20010301

Title: Pasteurella (Mannheimia) haemolytica leukotoxin-induced cytolysis of bovine leukocytes: role of arachidonic acid and its regulation.

Journal: Microbial pathogenesis 20010201

Title: PPARalpha activators inhibit tissue factor expression and activity in human monocytes.

Journal: Circulation 20010116

Title: Effects of polyunsaturated fatty acids and clofibrate on chicken stearoyl-coA desaturase 1 gene expression.

Journal: Biochemical and biophysical research communications 20010112

Title: Novel effects of 5,8,11-eicosatriynoic acid, a lipoxygenase inhibitor, on Ca2+ mobilization in Madin Darby canine kidney cells.

Journal: Pharmacology & toxicology 20010101

Title: The comparative release of FGF1 by hypoxia and temperature stress.

Journal: Growth factors (Chur, Switzerland) 20010101

Title: Role of platelets and the arachidonic acid pathway in the regulation of neutrophil oxidase activity.

Journal: Scandinavian journal of clinical and laboratory investigation 20010101

Title: Fibrate-modulated expression of fibrinogen, plasminogen activator inhibitor-1 and apolipoprotein A-I in cultured cynomolgus monkey hepatocytes -- role of the peroxisome proliferator-activated receptor-alpha.

Journal: Thrombosis and haemostasis 19981201

Title: PPAR alpha structure-function relationships derived from species-specific differences in responsiveness to hypolipidemic agents.

Journal: Biological chemistry 19970701

Title: Induction of cyclooxygenase-2 expression by peroxisome proliferators and non-tetradecanoylphorbol 12,13-myristate-type tumor promoters in immortalized mouse liver cells.

Journal: The Journal of biological chemistry 19970207

Title: Growth regulation by peroxisome proliferators: opposing activities in early and late G1.

Journal: Cancer research 19960715

Title: Inhibition of the Kv4 (Shal) family of transient K+ currents by arachidonic acid.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 19960415

Title: Polyunsaturated fatty acids inhibit hepatic stearoyl-CoA desaturase-1 gene in diabetic mice.

Journal: Lipids 19960301

Title: 5-Lipoxygenase products modulate the activity of the 85-kDa phospholipase A2 in human neutrophils.

Journal: The Journal of biological chemistry 19951103

Title: Fatty acids and retinoids control lipid metabolism through activation of peroxisome proliferator-activated receptor-retinoid X receptor heterodimers.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930315

Title: Modulation of interleukin-1 alpha mRNA expression in mouse epidermis by tumor promoters and antagonists.

Journal: Molecular carcinogenesis 19930101

Title: Mechanism of phosgene-induced lung toxicity: role of arachidonate mediators.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 19901101

Title: Parallel studies of His-DTrp-Ala-Trp-DPhe-Lys-NH2 and human pancreatic growth hormone-releasing factor-44-NH2 in rat primary pituitary cell monolayer culture.

Journal: Endocrinology 19850301

Title: Inhibition of steroid production in Leydig cells by non-steroidal anti-inflammatory and related compounds: evidence for the involvement of lipoxygenase products in steroidogenesis.

Journal: The Biochemical journal 19840415

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Title: Palumbo GJ, et, al. Inhibitors of the lipoxygenase pathway specifically block orthopoxvirus replication. Virology. 1991 Jan;180(1):457-63.

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Tags:1191-85-1 Molecular Formula|1191-85-1 MDL|1191-85-1 SMILES|1191-85-1 5,8,11,14-Eicosatetraynoic acid