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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 398
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
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
- Löslichkeit
- Soluble in methanol
- Aggregatzustand
- liquid
- pka
- 4.75 · 4.75±0.10(Predicted)
- Farbe
- Colorless to pale yellow
- Biologische Quelle
- fish oil
- Merck
- 14 · 14,3531
- BRN
- 1714433 · 1714433
- Stabilität
- 1 year · Stable for 1 year as supplied (unopened). After opening, EPA must be stored under inert gas at -80°C. Solutions in DMSO or ethanol should also be stored under inert gas and may be kept at -80°C for up to 2 months.
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONINGSKIN CONDITIONING - EMOLLIENT
- InChIKey
- RRGOKSYVAZDNKR-ARJAWSKDSA-N
- SMILES
- CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
- LogP
- 6.232 · 6.232 (est)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
Regulatorische Informationen
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- ridadr
- UN 3265 8/PG 3
- hs_code
- 29161900
- risk_code
- 34
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Speicherklasse
- 10 - Combustible liquids
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
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
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.
Verwendung und Herstellung
Anwendungen
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
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Ergänzende Hinweise
DefinitionChEBI: An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.
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