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Icosa-5,8,11,14-tetraensure
ARA · Arachidonate · Arachidonic · 5,8,11,14-EICOSATETRAENOIC ACID · icosa-5,8,11,14-tetraenoic acid · Arachidonic Acid (peroxide free) · (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid · 20:4n-6
Identifikatoren & physikalische Daten
| CAS No. | 506-32-1 |
|---|---|
| Summenformel | C20H32O2 |
| Durchschnittliche Molmasse | 304,5 g/mol |
| Monoisotopische Masse | 304,24023026 g/mol |
| SMILES | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O |
| InChIKey | YZXBAPSDXZZRGB-DOFZRALJSA-N |
| PubChem CID | 444899 |
| ChEMBL | CHEMBL15594 |
| ChEBI | CHEBI:15843 |
| EC No. | 208-033-4 |
| DTXSID | DTXSID4040420 |
| Lokaler Name | Icosa-5,8,11,14-tetraensure |
Chemische & physikalische Eigenschaften
| XLogP | 6,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 14 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 362 |
| LogP (Verteilungskoeffizient) | 6.98 |
| Siedepunkt | 170169-171 °C/0.15 mmHg (lit.) |
| Schmelzpunkt | -49.5-49 °C (lit.) |
| Dampfdruck | 0.00000015 [mmHg] |
| Physical Description | Liquid[Merck Index] |
| Kovats Retention Index | 2324.3 |
| Collision Cross Section | 182.1 Ų [M-H]- [CCS Type: DTBuffer gas: N2Sample Type: Human bronchoalveolar lavage fluid (BALF)Dataset: Unambiguous Lipids]178.94 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]182.21 Ų [M-H]- [CCS Type: DTMethod: stepped-field]183.66 Ų [M-H]- [CCS Type: DT179.8 Ų [M+Na]+181.6 Ų [M-H]-183 Ų [M-H]- |
| Dichte | 0.922 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.4872(lit.) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | ethanol: ≥10 mg/mLPRACTICALLY INSOLUBLE |
| Aggregatzustand | oil |
| pKa (Säurekonstante) | 4.75±0.10(Predicted) |
| Farbe | colorless to light yellow |
| Biologische Quelle | synthetic |
| Merck | 14,765 |
| BRN | 1713889 |
| Specific Activity | 200-240 Ci/mmol |
| Stabilität | Light Sensitive, Temperature Sensitive |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONINGSKIN CONDITIONING - EMOLLIENT |
| InChI | 1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15- |
| InChIKey | YZXBAPSDXZZRGB-DOFZRALJSA-N |
| SMILES | OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O |
| LogP (Verteilungskoeffizient) | 6.99 |
| CAS Datenbank | 506-32-1(CAS DataBase Reference) |
| NIST chemische Informationen | Arachidonic acid(506-32-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 10.3% (4 of 39) of reports.WarningH302 (84.6%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (82.1%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (89.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (89.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (79.5%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (84.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]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.Reported as not meeting GHS hazard criteria per 4 of 39 reports by companies.There are 5 notifications provided by 35 of 39 reports by companies with hazard statement code(s).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. |
|---|---|
| Regulatorische Informationen | 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. |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | May form explosive peroxidesMay cause irritationTargets the female reproductive system[Sigma-Aldrich MSDS] |
Anwendungen & Verwendung
Beschreibung
Arachidonic 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.).
Verwenden
Arachidonic 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.