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5,8,11,14,17-eicosapentaenoic acid

natural substances and extractives
2D:
3D:
CAS Number: 1553-41-9
FDA UNII: Search
Category: natural substances and extractives
IUPAC Name: 5,8,11,14,17-eicosapentaenoic acid
InChI : InChI=1/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)
Std.InChI: InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)
InChIKey : JAZBEHYOTPTENJ-UHFFFAOYAO
Std.InChIKey: JAZBEHYOTPTENJ-UHFFFAOYSA-N
SMILES : CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Molar Refractivity : 96.55 ± 0.3 cm3 (est)
Parachor : 785.6 ± 4.0 cm3 (est)
Index of Refraction : 1.512 ± 0.02 (est)
Surface Tension : 35.7 ± 3.0 dyne/cm (est)
Density : 0.941 ± 0.06 g/cm3 (est)
Polarizability : 38.27 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

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Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
water, 0.005814 mg/L @ 25 °C (est)

Cosmetic Information:

None found

Suppliers:

None found

Safety Information:

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:
natural substances and extractives
Recommendation for 5,8,11,14,17-eicosapentaenoic acid usage levels up to:
not for fragrance use.
Recommendation for 5,8,11,14,17-eicosapentaenoic acid flavor usage levels up to:
not for flavor use.

Safety References:

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3209
National Institute of Allergy and Infectious Diseases:Data
icosa-5,8,11,14,17-pentaenoic acid
Chemidplus:0001553419

References:

icosa-5,8,11,14,17-pentaenoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):3209
Pubchem (cas):1553-41-9

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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

fish oils
Search Trop PMC Picture

Synonyms:

icosa-5,8,11,14,17-pentaenoic acid
timnodonic acid

Articles:

PubMed:Mammalian ALOX15 orthologs exhibit pronounced dual positional specificity with docosahexaenoic acid.
J-Stage:Regulation of Lipid Metabolism by Palmitoleate and Eicosapentaenoic Acid (EPA) in Mice Fed a High-Fat Diet
PubMed:Omega-3 production by fermentation of Yarrowia lipolytica: From fed-batch to continuous.
PubMed:Fatty acids with in vitro binding affinity for human opioid receptors from the fungus Emericella nidulans.
PubMed:Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase.
PubMed:Polyunsaturated fatty acid levels in blood during pregnancy, at birth and at 7 years: their associations with two common FADS2 polymorphisms.
PubMed:Inhibitory activities of omega-3 Fatty acids and traditional african remedies on keloid fibroblasts.
PubMed:Anticholinesterase and antioxidant constituents from Gloiopeltis furcata.
PubMed:Teratogenic effects of diatom metabolites on sea urchin Paracentrotus lividus embryos.
PubMed:Biochemical composition of some red and brown macro algae from the Northeastern Mediterranean Sea.
PubMed:Comparison of fatty acid, mineral and proximate composition of body and legs of edible frog (Rana esculenta).
PubMed:Effects of different dietary fatty acids on the fatty acid compositions and the expression of lipid metabolic-related genes in mammary tumor tissues of rats.
PubMed:Acanthopleuribacter pedis gen. nov., sp. nov., a marine bacterium isolated from a chiton, and description of Acanthopleuribacteraceae fam. nov., Acanthopleuribacterales ord. nov., Holophagaceae fam. nov., Holophagales ord. nov. and Holophagae classis nov. in the phylum 'Acidobacteria'.
PubMed:Fat content and fatty acid compositions of 34 marine water fish species from the Mediterranean Sea.
PubMed:Cold adaptation of eicosapentaenoic acid-less mutant of Shewanella livingstonensis Ac10 involving uptake and remodeling of synthetic phospholipids containing various polyunsaturated fatty acids.
PubMed:Seasonal effects in the nutritional quality of the body structural tissue of cephalopods.
PubMed:Intermolecular peroxyl radical reactions during autoxidation of hydroxy and hydroperoxy arachidonic acids generate a novel series of epoxidized products.
PubMed:The quality properties and saturated and unsaturated fatty acid profiles of quail egg: the alterations of fatty acids with process effects.
PubMed:Oxidized derivatives of omega-3 fatty acids: identification of IPF3 alpha-VI in human urine.
PubMed:Properties of trans isomers of eicosapentaenoic acid and docosahexaenoic acid methyl esters on cyanopropyl stationary phases.
PubMed:Effects of cis-unsaturated free fatty acids on PKC-epsilon activation and nicotinic ACh receptor responses.
PubMed:Activating omega-6 polyunsaturated fatty acids and inhibitory purine nucleotides are high affinity ligands for novel mitochondrial uncoupling proteins UCP2 and UCP3.
PubMed:Upgrading of maatjes herring byproducts: production of crude fish oil.
PubMed:Prevention of sudden cardiac death by dietary pure omega-3 polyunsaturated fatty acids in dogs.
PubMed:Effects of eicosapentaenoic acid and its 15-hydroperoxy and 15-hydroxy derivatives on glucosamine synthetase activity in rabbit gastric mucosa.
PubMed:The membrane lipids of the marine ciliated protozoan Parauronema acutum.
PubMed:Dietary essential fatty acid deficiency differentially affects tissues of rats.
PubMed:Modification of cultured Madin-Darby canine kidney cells with dietary unsaturated fatty acids and regulation of arachidonate cascade reaction.
PubMed:15-Hydroperoxyeicosapentaenoic acid inhibits arachidonic acid metabolism in rabbit platelets more potently than eicosapentaenoic acid.
PubMed:Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration.
PubMed:Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils.
PubMed:Blocking effects of polyunsaturated fatty acids on Na+ channels of neonatal rat ventricular myocytes.
PubMed:Development and characterization of essential fatty acid deficiency in human endothelial cells in culture.
PubMed:Modulation of the beta-adrenergic response of cardiomyocytes by specific lipoxygenase products involves their incorporation into phosphatidylinositol and activation of protein kinase C.
PubMed:[Eicosanoids as mediators in ARDS].
PubMed:Bio-anticlastogenic effects of unsaturated fatty acids included in fish oil--docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid--in cultured Chinese hamster cells.
PubMed:The enteral bioavailability of eicosapentaenoic acid and docosahexaenoic acid is as good from ethyl esters as from glyceryl esters in spite of lower hydrolytic rates by pancreatic lipase in vitro.
PubMed:[Inactivation of prostaglandin H synthase from sheep vesicular glands with acetylenic fatty acids].
PubMed:Stearidonic acid, an inhibitor of the 5-lipoxygenase pathway. A comparison with timnodonic and dihomogammalinolenic acid.
PubMed:Effect of cultural conditions on production of eicosapentaenoic acid by Pythium irregulare.
PubMed:Differential effects of omega-3 fish oils on protein kinase activities in vitro.
PubMed:Dietary fish and prostanoid formation in man.
PubMed:Influence of dietary fish on eicosanoid metabolism in man.
PubMed:Transformation of 15-hydroperoxide of eicosapentaenoic acid to lipoxins and trihydroxyeicosatetraenoic acids by 5-lipoxygenase partially purified from potato tubers.
PubMed:[General pharmacological studies on 5,8,11,14,17-eicosapentaenoic acid ethyl ester (EPA-E)].
PubMed:Fatty acid composition of umbilical arteries and veins: possible implications for the fetal EFA-status.
PubMed:[Effects of omega-3-fatty acids on the prostaglandin system in healthy probands].
PubMed:Habitual fish consumption, fatty acids of serum phospholipids and platelet function.
PubMed:Normalization by dietary cod-liver oil of reduced thrombogenesis in essential fatty acid deficient rats.
PubMed:Effect of a fish oil diet on the composition of rat neutrophil lipids and the molecular species of choline and ethanolamine glycerophospholipids.
PubMed:Comparison between habitual intake of polyunsaturated fatty acids and their concentrations in serum lipid fractions.
PubMed:Eskimo plasma constituents, dihomo-gamma-linolenic acid, eicosapentaenoic acid and docosahexaenoic acid inhibit the release of atherogenic mitogens.
PubMed:Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes.
PubMed:Modulation of the contractile activity of the guinea-pig lung parenchymal strip by exogenous 5,8,11,14,17-eicosapentaenoic acid.
PubMed:Quantitative determination of prostaglandins E1, E2 and E3 in frog tissue.
PubMed:Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesis.
PubMed:Transformation of 15-hydroperoxyeicosapentaenoic acid to lipoxin A5 and B5, mono- and dihydroxyeicosapentaenoic acids by porcine leukocytes.
PubMed:Effect of exogenous 5,8,11,14,17-eicosapentaenoic acid on cardiac anaphylaxis.
PubMed:Modulation of the anaphylactic reaction in sensitized guinea-pig hearts by timnodonic acid.
PubMed:Modulation of the contractile activity of the guinea-pig lung parenchymal strip by timnodonic acid.
PubMed:Effect of dietary menhaden oil on tumor cell loss and the accumulation of mass of a transplantable mammary adenocarcinoma in BALB/c mice.
PubMed:Formation of hepoxilin A4, B4 and the corresponding trioxilins from 12(S)-hydroperoxy-5,8,10,14,17-icosapentaenoic acid.
PubMed:Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid.
PubMed:Lipoxene: a new group of trihydroxy pentaenes of eicosapentaenoic acid derived from porcine leukocytes.
PubMed:Studies on arachidonate 5-lipoxygenase of rat basophilic leukemia cells.
PubMed:Eicosapentaenoic acid: its effects on arachidonic acid metabolism by cells in culture.
PubMed:Effect of omega-3 fatty acids on growth of a rat mammary tumor.
PubMed:Arachidonic acid, 5,8,11-eicosatrienoic acid and 5,8,11,14, 17-eicosapentaenoic acid. Dietary manipulation of the levels of these acids in rat liver and platelet phospholipids and their incorporation into human platelet lipids.
PubMed:Dietary fish oil augments the induction of arthritis in rats immunized with type II collagen.
PubMed:Dietary alpha-linolenic acid and prostaglandin synthesis: a time course study.
PubMed:Sera fatty acid effects on cultured rat splenocytes.
PubMed:Arachidonate 5-lipoxygenase of guinea pig peritoneal polymorphonuclear leukocytes. Activation by adenosine 5'-triphosphate.
PubMed:Partial purification and characterization of arachidonate 12-lipoxygenase from rat lung.
PubMed:Distinctive selectivity for docosatetraenoic acid incorporation by Ehrlich ascites tumor cells.
PubMed:Human umbilical blood vessel converts all cis-5, 8, 11, 14, 17 eicosapentaenoic acid to prostaglandin I3.
PubMed:Formation of leukotrienes E3, E4 and E5 in rat basophilic leukemia cells.
PubMed:Metabolism of radioactive 5,8,11,14,17-eicosapentaenoic acid by human platelets.
PubMed:The influence of ambient peroxides on the conversion of 5,8,11,14,17-eicosapentaenoic acid to prostaglandins.
PubMed:Transformations of 5,8,11,14,17-eicosapentaenoic acid in human platelets.
PubMed:All cis-5, 8, 11, 14, 17 eicosapentaenoic acid and triene prostaglandins: potential anti-thrombotic agents.
PubMed:The effect of arachidonic- and eicosapentaenoic acid on the synthesis of prostacyclin-like material in human umbilical vasculature.
PubMed:Manipulation of platelet aggregation by prostaglandins and their fatty acid precursors: pharmacological basis for a therapeutic approach.
PubMed:Effects of all cis-5,8,11,14,17 eicosapentaenoic acid and PGH3 on platelet aggregation.
PubMed:Preparation and biochemical properties of PGH3.
PubMed:Haemostatic function and platelet polyunsaturated fatty acids in Eskimos.
PubMed:Methyl-directed desaturation of arachidonic to eicosapentaenoic acid in the fungus, Saprolegnia parasitica.
PubMed:Synthesis and function of 9,12,15-octadecatrien-6-ynoic acid in the moss ceratodon purpureus.
PubMed:On the phospholipase activity in bovine seminal vesicles and its possible role in the regulation of the prostaglandin biosynthesis.
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