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34450-18-5,MFCD00077382
Catalog No.:AA0032LD

34450-18-5 | 17-Octadecynoic acid

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1mg
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5mg
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10mg
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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0032LD
Chemical Name:
17-Octadecynoic acid
CAS Number:
34450-18-5
Molecular Formula:
C18H32O2
Molecular Weight:
280.4455
MDL Number:
MFCD00077382
SMILES:
C#CCCCCCCCCCCCCCCCC(=O)O
Properties
Properties
 
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
262  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
15  
XLogP3:
7.1  

Downstream Synthesis Route

[1]Menger;Chen;Brocchini;Hopkins;Hamilton[JournaloftheAmericanChemicalSociety,1993,vol.115,#15,p.6600-6608]

Literature

Title: 2-Alkynoic fatty acids inhibit topoisomerase IB from Leishmania donovani.

Journal: Bioorganic & medicinal chemistry letters 20121001

Title: Bioorthogonal proteomics of 15-hexadecynyloxyacetic acid chemical reporter reveals preferential targeting of fatty acid modified proteins and biosynthetic enzymes.

Journal: Bioorganic & medicinal chemistry 20120115

Title: DHHC5 protein palmitoylates flotillin-2 and is rapidly degraded on induction of neuronal differentiation in cultured cells.

Journal: The Journal of biological chemistry 20120102

Title: 17-Octadecynoic acid improves contractile response to angiotensin II by releasing vasocontrictor prostaglandins.

Journal: Prostaglandins & other lipid mediators 20120101

Title: Global profiling of dynamic protein palmitoylation.

Journal: Nature methods 20120101

Title: Arachidonic acid inhibits Na⁺-K⁺-ATPase via cytochrome P-450, lipoxygenase and protein kinase C-dependent pathways in sheep pulmonary artery.

Journal: Vascular pharmacology 20120101

Title: iPLA2β overexpression in smooth muscle exacerbates angiotensin II-induced hypertension and vascular remodeling.

Journal: PloS one 20120101

Title: Proteomic analysis of S-acylated proteins in human B cells reveals palmitoylation of the immune regulators CD20 and CD23.

Journal: PloS one 20120101

Title: P-450-dependent epoxygenase pathway of arachidonic acid is involved in myeloma-induced angiogenesis of endothelial cells.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20111001

Title: Species differences in intestinal metabolic activities of cytochrome P450 isoforms between cynomolgus monkeys and humans.

Journal: Drug metabolism and pharmacokinetics 20110601

Title: Contribution of Ras farnesyl transferase, MAP kinase and cytochrome P-450 metabolites to endothelin-1 induced hypertension.

Journal: Bosnian journal of basic medical sciences 20110501

Title: Lipid-cell interactions in human monocytes investigated by doubly-resonant coherent anti-Stokes Raman scattering microscopy.

Journal: Journal of biomedical optics 20110201

Title: The role of palmitoylation in signalling, cellular trafficking and plasma membrane localization of protease-activated receptor-2.

Journal: PloS one 20110101

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

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Onset of pulmonary ventilation in fetal sheep produces pial arteriolar constriction dependent on cytochrome p450 omega-hydroxylase activity.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20100801

Title: Protease-activated receptor 2 and bradykinin-mediated vasodilation in the cerebral arteries of stroke-prone rats.

Journal: Peptides 20100201

Title: CYP-omega-hydroxylation-dependent metabolites of arachidonic acid inhibit the basolateral 10 pS chloride channel in the rat thick ascending limb.

Journal: Kidney international 20091001

Title: Large-scale profiling of protein palmitoylation in mammalian cells.

Journal: Nature methods 20090201

Title: Cytochrome P450 omega-hydroxylase inhibition reduces cardiomyocyte apoptosis via activation of ERK1/2 signaling in rat myocardial ischemia-reperfusion.

Journal: European journal of pharmacology 20081031

Title: Antiangiogenic effect of inhibitors of cytochrome P450 on rats with glioblastoma multiforme.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20080801

Title: 20-Hydroxyeicosatetraenoic acid inhibits the apoptotic responses in pulmonary artery smooth muscle cells.

Journal: European journal of pharmacology 20080624

Title: Endothelial dysfunction and improvement of the angiotensin II-reactivity in hypercholesterolemic rabbits: role of cyclooxygenase metabolites.

Journal: European journal of pharmacology 20080202

Title: Cytosolic phospholipase A2 and arachidonic acid metabolites modulate ventilator-induced permeability increases in isolated mouse lungs.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20080201

Title: Role of 20-HETE in the hypoxia-induced activation of Ca2+-activated K+ channel currents in rat cerebral arterial muscle cells.

Journal: American journal of physiology. Heart and circulatory physiology 20080101

Title: Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20071101

Title: Role of 20-HETE in D1/D2 dopamine receptor synergism resulting in the inhibition of Na+-K+-ATPase activity in the proximal tubule.

Journal: American journal of physiology. Renal physiology 20070501

Title: High dietary salt reduces the contribution of 20-HETE to arteriolar oxygen responsiveness in skeletal muscle.

Journal: American journal of physiology. Heart and circulatory physiology 20070301

Title: Vascular dysfunction in type 2 diabetic TallyHo mice: role for an increase in the contribution of PGH2/TxA2 receptor activation and cytochrome p450 products.

Journal: Canadian journal of physiology and pharmacology 20070101

Title: Pharmacological characteristics of endothelium-derived hyperpolarizing factor-mediated relaxation of small mesenteric arteries from db/db mice.

Journal: European journal of pharmacology 20061203

Title: Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.

Journal: Journal of lipid research 20061201

Title: CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime].

Journal: Drug metabolism and disposition: the biological fate of chemicals 20061201

Title: Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid.

Journal: FEBS letters 20060710

Title: Omega-oxidation of very long-chain fatty acids in human liver microsomes. Implications for X-linked adrenoleukodystrophy.

Journal: The Journal of biological chemistry 20060512

Title: ROS-sensitive cytochrome P450 activity maintains endothelial dilatation in ageing but is transitory in dyslipidaemic mice.

Journal: British journal of pharmacology 20060401

Title: Regulation of potassium channels in coronary smooth muscle by adenoviral expression of cytochrome P-450 epoxygenase.

Journal: American journal of physiology. Heart and circulatory physiology 20060101

Title: Transfection of cytochrome P4504B1 into the cornea increases angiogenic activity of the limbal vessels.

Journal: The Journal of pharmacology and experimental therapeutics 20051001

Title: Effects of epoxyeicosatrienoic acids on levels of eNOS phosphorylation and relevant signaling transduction pathways involved.

Journal: Science in China. Series C, Life sciences 20051001

Title: Enhanced release of endothelium-derived hyperpolarizing factor in small coronary arteries from rats with congestive heart failure.

Journal: Clinical and experimental pharmacology & physiology 20050801

Title: Mediators involved in decreasing peripheral vascular resistance with carbachol in the rat hind limb perfusion model.

Journal: Journal of pharmacological sciences 20050701

Title: Comparison of muscarinic receptor- and beta-adrenoceptor-mediated vasorelaxation between euthyroid and acute hyperthyroid rats.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20050701

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: Evidence for two enzymatic pathways for omega-oxidation of docosanoic acid in rat liver microsomes.

Journal: Journal of lipid research 20050501

Title: The synthesis of 20-HETE in small porcine coronary arteries antagonizes EDHF-mediated relaxation.

Journal: Cardiovascular research 20050201

Title: Redundant signaling mechanisms contribute to the vasodilatory response of the afferent arteriole to proteinase-activated receptor-2.

Journal: American journal of physiology. Renal physiology 20050101

Title: Role of hydrogen peroxide in ACh-induced dilation of human submucosal intestinal microvessels.

Journal: American journal of physiology. Heart and circulatory physiology 20050101

Title: Involvement of NO and EDHF in flow-induced vasodilation in isolated hamster cremasteric arterioles.

Journal: Journal of vascular research 20050101

Title: Cytochrome P450 omega-hydroxylase inhibition reduces infarct size during reperfusion via the sarcolemmal KATP channel.

Journal: Journal of molecular and cellular cardiology 20041201

Title: Design and synthesis of 1-(4-benzoylphenyl)imidazole derivatives as new potent 20-HETE synthase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20041101

Title: Inhibition of cytochrome P450omega-hydroxylase: a novel endogenous cardioprotective pathway.

Journal: Circulation research 20041015

Title: Arachidonic acid relaxes human pulmonary arteries through K+ channels and nitric oxide pathways.

Journal: European journal of pharmacology 20041006

Title: Changes in renal haemodynamics induced by indomethacin in the rat involve cytochrome P450 arachidonic acid-dependent epoxygenases.

Journal: Clinical and experimental pharmacology & physiology 20041001

Title: Essential role of EDHF in the initiation and maintenance of adrenergic vasomotion in rat mesenteric arteries.

Journal: American journal of physiology. Heart and circulatory physiology 20040801

Title: Activation of Na+-independent Mg2+ efflux by 20-hydroxyeicosatetraenoic acid in rat renal epithelial cells.

Journal: The Japanese journal of physiology 20040801

Title: P2Y purine receptor responses and expression in the pulmonary circulation of juvenile rabbits.

Journal: American journal of physiology. Heart and circulatory physiology 20040701

Title: Acute hyperthyroidism alters adrenoceptor- and muscarinic receptor-mediated responses in isolated rat renal and femoral arteries.

Journal: European journal of pharmacology 20040616

Title: Cytochrome P-450 metabolites in endothelin-stimulated cardiac hormone secretion.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20040501

Title: Distinct roles for protease-activated receptors 1 and 2 in vasomotor modulation in rat superior mesenteric artery.

Journal: Cardiovascular research 20040301

Title: Role of EETs in regulation of endothelial permeability in rat lung.

Journal: American journal of physiology. Lung cellular and molecular physiology 20040201

Title: Bidirectional regulation of renal cortical Na+,K+-ATPase by protein kinase C.

Journal: Acta biochimica Polonica 20040101

Title: Arachidonic acid-activated Na+-dependent Mg2+ efflux in rat renal epithelial cells.

Journal: Biochimica et biophysica acta 20031203

Title: Cytochrome P-450 metabolites but not NO, PGI2, and H2O2 contribute to ACh-induced hyperpolarization of pressurized canine coronary microvessels.

Journal: American journal of physiology. Heart and circulatory physiology 20031101

Title: Arachidonic acid metabolites contribute to the irreversible depolarization induced by in vitro ischemia.

Journal: Journal of neurophysiology 20031101

Title: Determinants of renal afferent arteriolar actions of bradykinin: evidence that multiple pathways mediate responses attributed to EDHF.

Journal: American journal of physiology. Renal physiology 20030901

Title: Adrenomedullin-induced endothelium-dependent relaxation in porcine ciliary arteries.

Journal: Investigative ophthalmology & visual science 20030901

Title: Dopamine D1 receptor-dependent inhibition of NaCl transport in the rat thick ascending limb: mechanism of action.

Journal: European journal of pharmacology 20030725

Title: Cytochrome p-450 epoxygenase products contribute to attenuated vasoconstriction after chronic hypoxia.

Journal: American journal of physiology. Heart and circulatory physiology 20030701

Title: Electron spin resonance detection of hydrogen peroxide as an endothelium-derived hyperpolarizing factor in porcine coronary microvessels.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20030701

Title: Nitric oxide decreases renal medullary Na+, K+-ATPase activity through cyclic GMP-protein kinase G dependent mechanism.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20030601

Title: Effects of H2O2 on membrane potential of smooth muscle cells in rabbit mesenteric resistance artery.

Journal: European journal of pharmacology 20030319

Title: Mechanisms of hydrogen-peroxide-induced biphasic response in rat mesenteric artery.

Journal: British journal of pharmacology 20030301

Title: An endothelium-derived factor modulates purinergic neurotransmission to mesenteric arterial smooth muscle of hamster.

Journal: European journal of pharmacology 20030214

Title: Endothelium-derived hyperpolarizing factor in human internal mammary artery is 11,12-epoxyeicosatrienoic acid and causes relaxation by activating smooth muscle BK(Ca) channels.

Journal: Circulation 20030211

Title: Norepinephrine-induced stimulation of p38 mitogen-activated protein kinase is mediated by arachidonic acid metabolites generated by activation of cytosolic phospholipase A(2) in vascular smooth muscle cells.

Journal: The Journal of pharmacology and experimental therapeutics 20030201

Title: Regulation of renal Na(+),K(+)-ATPase and ouabain-sensitive H(+),K(+)-ATPase by the cyclic AMP-protein kinase A signal transduction pathway.

Journal: Acta biochimica Polonica 20030101

Title: Acute decrease of cerebrocortical microflow and lack of carbon dioxide reactivity following subarachnoid haemorrhage in the rat.

Journal: Acta neurochirurgica. Supplement 20030101

Title: Oxidant stress-induced increase in myogenic activation of skeletal muscle resistance arteries in obese Zucker rats.

Journal: American journal of physiology. Heart and circulatory physiology 20021201

Title: Nitric oxide contributes to 20-HETE-induced relaxation of pulmonary arteries.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20021001

Title: EDHF, but not NO or prostaglandins, is critical to evoke a conducted dilation upon ACh in hamster arterioles.

Journal: American journal of physiology. Heart and circulatory physiology 20020901

Title: 20-HETE pathway antagonists inhibit rat small mesenteric artery tone.

Journal: Microvascular research 20020901

Title: Role of 20-hydroxyeicosatetraenoic acid in the renal and vasoconstrictor actions of angiotensin II.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20020701

Title: 20-HETE contributes to the acute fall in cerebral blood flow after subarachnoid hemorrhage in the rat.

Journal: American journal of physiology. Heart and circulatory physiology 20020401

Title: Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes.

Journal: The Journal of pharmacology and experimental therapeutics 20020101

Title: Multiple mechanisms of vascular smooth muscle relaxation by the activation of proteinase-activated receptor 2 in mouse mesenteric arterioles.

Journal: British journal of pharmacology 20020101

Title: Differential effect of cytochrome P-450 omega-hydroxylase inhibition on O2-induced constriction of arterioles in SHR with early and established hypertension.

Journal: Microcirculation (New York, N.Y. : 1994) 20011201

Title: Initial and sustained phases of myogenic response of rat mesenteric small arteries.

Journal: American journal of physiology. Heart and circulatory physiology 20011101

Title: Role of prostanoids and 20-HETE in mediating oxygen-induced constriction of skeletal muscle resistance arteries.

Journal: Microvascular research 20011101

Title: Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.

Journal: British journal of pharmacology 20011101

Title: Expressed CYP4A4 metabolism of prostaglandin E(1) and arachidonic acid.

Journal: Archives of biochemistry and biophysics 20010915

Title: Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles.

Journal: Hypertension research : official journal of the Japanese Society of Hypertension 20010901

Title: Further investigations into the endothelium-dependent hyperpolarizing effects of bradykinin and substance P in porcine coronary artery.

Journal: British journal of pharmacology 20010801

Title: Mediation of EDHF-induced reduction of smooth muscle [Ca(2+)](i) and arteriolar dilation by K(+) channels, 5,6-EET, and gap junctions.

Journal: Microcirculation (New York, N.Y. : 1994) 20010801

Title: Activation of the phosphatidylinositol 3-kinase-Akt/protein kinase B signaling pathway in arachidonic acid-stimulated human myeloid and endothelial cells: involvement of the ErbB receptor family.

Journal: The Journal of biological chemistry 20010720

Title: Activation of cardiac afferents by arachidonic acid: relative contributions of metabolic pathways.

Journal: American journal of physiology. Heart and circulatory physiology 20010701

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

Journal: Kidney international 20010601

Title: Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels.

Journal: Circulation 20010417

Title: Cytochrome P-450 omega-hydroxylase: a potential O(2) sensor in rat arterioles and skeletal muscle cells.

Journal: American journal of physiology. Heart and circulatory physiology 20010401

Title: Altered mechanisms underlying hypoxic dilation of skeletal muscle resistance arteries of hypertensive versus normotensive Dahl rats.

Journal: Microcirculation (New York, N.Y. : 1994) 20010401

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

Journal: Lipids 20010401

Title: EDHF contributes to strain-related differences in pulmonary arterial relaxation in rats.

Journal: American journal of physiology. Lung cellular and molecular physiology 20010301

Title: 20-HETE modulates myogenic response of skeletal muscle resistance arteries from hypertensive Dahl-SS rats.

Journal: American journal of physiology. Heart and circulatory physiology 20010301

Title: Bradykinin attenuates the [Ca(2+)](i) response to angiotensin II of renal juxtamedullary efferent arterioles via an EDHF.

Journal: British journal of pharmacology 20010201

Title: Role of 20-HETE in mediating the effect of dietary K intake on the apical K channels in the mTAL.

Journal: American journal of physiology. Renal physiology 20010201

Title: 20-HETE contributes to myogenic activation of skeletal muscle resistance arteries in Brown Norway and Sprague-Dawley rats.

Journal: Microcirculation (New York, N.Y. : 1994) 20010201

Title: Relative contributions of cyclooxygenase- and cytochrome P450 omega-hydroxylase-dependent pathways to hypoxic dilation of skeletal muscle resistance arteries.

Journal: Journal of vascular research 20010101

Title: Leukotriene B4 omega-hydroxylase in human polymorphonuclear leukocytes. Suicidal inactivation by acetylenic fatty acids.

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Title: Jiang S, et al. β-adrenergic Receptor-stimulated Cardiac Myocyte Apoptosis: Role of Cytochrome P450 ω-hydroxylase. J Cardiovasc Pharmacol. 2017;70(2):94-101.

Title: Zou AP, et al. Effects of 17-octadecynoic acid, a suicide-substrate inhibitor of cytochrome P450 fatty acid omega-hydroxylase, on renal function in rats. J Pharmacol Exp Ther. 1994;268(1):474-481.

Title: Nithipatikom K, et al. Inhibition of cytochrome P450omega-hydroxylase: a novel endogenous cardioprotective pathway. Circ Res. 2004;95(8):e65-e71.

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