Icosapent

HCID 446284CAS 10417-94-4

Grundinformationen

Standard-SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChIKey
JAZBEHYOTPTENJ-JLNKQSITSA-N
Summenformel
C20H30O2
Durchschnittliche Molmasse
302,5 g/mol
Monoisotopische Masse
302,2245802

Namen und Bezeichner

Bevorzugter Name
Icosapent
IUPAC
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Englischer Name
EPA
Summenformel
C20H30O2
Molmasse
302.45

Namen und Synonyme

IcosapentEPAIcosapentoIcosapentumMiraxionEye QEye-QRopufa 70Incromega e 7010srCCRIS 3279AAN7QOV9EAUNII-AAN7QOV9EA
Weitere Namen anzeigen
EICOSAPENTAENOIC ACIDCIS-5,8,11,14,17-EICOSAPENTAENOIC ACIDEicosapentaenoicTIMNODONIC ACIDEPA (Eicosapentaenoic Acid)Eicosapentaenoic acid (EPA)5C,8C,11C,14C,17C-EICOSAPENTAENOIC ACID5,8,11,14,17-EICOSAPENTAENOIC ACIDALL CIS-5,8,11,14,17-EICOSAPENTAENOIC ACID
EPA 45GEPA [drug](5Z,8Z,11Z,14Z,17Z)-EicosapentaenoateIcosapentum [INN-Latin]Icosapento [INN-Spanish]C20:5 (n-3)CHEBI:28364C20:5n-3,6,9,12,15

Datenbank-Bezeichner

CAS
10417-94-4
PubChem CID
446284
DTXSID
DTXSID9041023
ChEMBL
CHEMBL460026
ChEBI
CHEBI:28364
UNII
AAN7QOV9EA
EC Number
600-528-7
Nikkaji
J343.473G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
37,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
13
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

LogP6.1
Physical DescriptionLiquid
Kovats Retention Index2334.2;2327.7
Collision Cross Section · 2 Einträge

180.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]

178.53 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physikochemische Eigenschaften

Schmelzpunkt
54 · −54-−53 °C(lit.)
Siedepunkt
439 ℃ · 439℃
Dichte
0.943 g/mL · 0.943 g/mL at 25 °C(lit.)
Brechungsindex
20 · n20/D 1.4977(lit.)
Flammpunkt
93 °C · 93 °C
storage temp.
-20 °C · -20°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 92 reports by companies from 1 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Corr. 1B (100%)

Regulatorische Informationen

Regulatory Information5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Sicherheitsdaten

F
8-10-23
wgk
3
ridadr
UN 3265 8/PG 3
hs_code
29161900
risk_code
34
hazard_code
C

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.

Mechanism of Action · 1 Eintrag

The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40.

Metabolism/MetabolitesEicosapentaenoic acid has known human metabolites that include Juniperonic acid.
Tissue LocationsAdipose Tissue;Epidermis;Erythrocyte;Fibroblasts;Kidney;Leukocyte;Liver;Placenta;Platelet;Skeletal Muscle
Cellular LocationsExtracellular;Membrane
Metabolite Pathwaysalpha-Linolenic acid metabolism

Verwendung und Herstellung

Use ClassificationCosmetics -> Emollient; Skin conditioning
Anwendungen · 1 Eintrag

Verwendencis-5,8,11,14,17-Eicosapentaenoic acid has been used:to test pharmacologic effect on steatosis in hepatocytesas an analytical standard in Raman spectra measurements to characterize human breast cancer samplesin lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.

Zugehörige Reaktionen

32

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