Icosa-5,8,11,14-tetraensure
Arachidonic Acid
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Grundinformationen
- CAS
506-32-1- Standard-SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O- InChIKey
YZXBAPSDXZZRGB-DOFZRALJSA-N- Summenformel
- C20H32O2
- Durchschnittliche Molmasse
- 304,5 g/mol
- Monoisotopische Masse
- 304,24023026
Überblick
Arachidonic acid is a long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. It has a role as a mouse metabolite, a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor and a Daphnia galeata metabolite. It is a long-chain fatty acid, an omega-6 fatty acid and an icosa-5,8,11,14-tetraenoic acid. It is a conjugate acid of an arachidonate. It derives from a hydride of a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene.
Namen und Bezeichner
- Bevorzugter Name
- Arachidonic Acid
- IUPAC
- (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
- Lokaler Name
- Icosa-5,8,11,14-tetraensure
- Englischer Name
- Arachidonic acid
- Summenformel
- C20H32O2
- Molmasse
- 304.47
Namen und Synonyme
arachidonic acid506-32-1(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid(all-Z)-5,8,11,14-Eicosatetraenoic acidcis-5,8,11,14-Eicosatetraenoic acid5Z,8Z,11Z,14Z-eicosatetraenoic acid5,8,11,14-Eicosatetraenoic acid, (all-Z)-Arachidonate, Sodiumall-cis-5,8,11,14-eicosatetraenoic acid(5Z,8Z,11Z,14Z)-Icosatetraenoic acid27YG812J1IFatty Acid 20:4 n-6
Weitere Namen anzeigen
ARAArachidonateArachidonic5,8,11,14-EICOSATETRAENOIC ACIDicosa-5,8,11,14-tetraenoic acidArachidonic Acid (peroxide free)20:4n-6Single-Use Arachidonic Acid (peroxide free)
C20:4DTXSID4040420CHEBI:15843All-cis-icosa-5,8,11,14-tetraenoic acidRefChem:5560DTXCID2020420208-033-4Immunocytophyte
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 6,3
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 14
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 362
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Fatty Acids and Fats
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Cosmetics
Cosmetic ingredients (Arachidonic Acid) -> CIR (Cosmetic Ingredient Review)
Emollient
SpringerMaterials PropertiesChemical diffusion
LogP
6.98
6.98
Vapor Pressure0.00000015 [mmHg]
Physical Description
Liquid; [Merck Index]
Liquid
Collision Cross Section
182.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 10.3% (4 of 39) of reports.
Warning
H302 (84.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: 5,8,11,14-Eicosatetraenoic acid, (all-Z)-
5,8,11,14-Eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-: 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.
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryMay form explosive peroxides; May cause irritation; Targets the female reproductive system; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (84.6%)
Toxikologische Informationen
Toxicity Summary
The safety of this ingredient has not been documented and substantiated for cosmetic product use. The CIR Expert Panel cannot conclude whether Arachidonic Acid is safe for use in cosmetic products until such time that the appropriate safety data have been obtained and evaluated.
Chemie und Industrie
Pharmakologische Informationen
Metabolism/MetabolitesArachidonic acid has known human metabolites that include 8,9-EET, 5,6-EET, 20-HETE, 8-HETE, 18-HETE, 11,12-EET, 13-HETE, 7-HETE, 17-HETE, 15-HETE, 14,15-EET, 11-HETE, 12-HETE, 5-HETE, 16-HETE, 9-HETE, 19-HETE, and 10-HETE.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysAcetaminophen Action Pathway
Verwendung und Herstellung
Uses
CIR ingredient: Arachidonic Acid
Essential fatty acid for animals and humans; Used as a nutrient and for the treatment of eczema in dogs and swine; [Merck Index]
Use ClassificationCosmetics -> Emollient
Anwendungen
BeschreibungArachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is the counterpart to the saturated arachidic acid found in peanut oil, (L. arachis – peanut.).
VerwendenArachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Zugehörige Reaktionen
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