methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate
(-)-leukotriene A4 · LEUKOTRIENE A4 METHYL ESTER · PWXYNAKNLZUYAL-WAQVJNLQSA-N · (-)-Leukotriene A4 methyl ester · LTA4 (Leukotriene A4 methyl ester) · 5S-TRANS-5,6-OXIDO-7E,9E,11Z,14Z-EICOSATETRAENOIC ACID, METHYL ESTER · LEUKOTRIENE A4-METHYLESTER SOLUTION (100UG/ML HEXANE/1% TRIETHYLAMINE) · 14,15-Leukotriene A4 methyl ester, Inhibitor of Leukotriene A4 hydrolase
![Molekülstruktur von methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate](/img/chemical/6478221.png)
Identifikatoren & physikalische Daten
| CAS No. | 73466-12-3 |
|---|---|
| Summenformel | C21H32O3 |
| Durchschnittliche Molmasse | 332,5 g/mol |
| Monoisotopische Masse | 332,23514488 g/mol |
| SMILES | CCCCC/C=C\C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(=O)OC |
| InChIKey | WTKAVFHPLJFCMZ-NIBLXIPLSA-N |
| PubChem CID | 6478221 |
| EC No. | 633-240-5 |
| DTXSID | DTXSID10424293 |
Chemische & physikalische Eigenschaften
| XLogP | 5,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 14 |
| Schwere Atome | 24 |
| Formalladung | 0 |
| Komplexität | 446 |
| Siedepunkt | 442.453±25.00 °C(Press: 760.00 Torr)(predicted) |
| Dichte | 0.998±0.06 g/cm3(Temp: 25 °CPress: 760 Torr)(predicted) |
| Lagerbedingungen | −20°C |
| Löslichkeit | Acetone: >50 mg/mlDMF: >50 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS pH 7.2: insoluble and unstable. |
| Aggregatzustand | triethylamine:hexane solution |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Flam. Liq. 2 (100%) |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN 1208 3/PG 2 |
| R-Sätze (R) | 11-36/37/38-48/20-51/53-62-65-67 |
| Gefahrensymbole | F,Xn,N |
| Sicherheitshinweise (S) | 9-16-29-33-36/37-61-62 |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrenklasse | Aquatic Chronic 2Asp. Tox. 1Eye Irrit. 2Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 1 InhalationSTOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Leukotriene A4 (LTA4) is synthesized in mast cells, eosinophils, and neutrophils from arachidonic acid by 5-lipoxygenase (5-LO), which exhibits both lipoxygenase and LTA4 synthase activities. LTA4 is rapidly metabolized by LTA4 hydrolase or LTC4 synthase to LTB4 or LTC4, respectively. LTA4, from leukocytes, is known to undergo transcellular metabolism in platelets, erythrocytes, and endothelial cells. Further metabolism of LTA4 by 15-LO leads to lipoxin biosynthesis. LTA4 as a free acid is highly unstable. The methyl ester is stable and can be readily hydrolyzed to the free acid as needed.
Verwenden
LTA4 (Leukotriene A4 methyl ester) is an unstable intermediate in the biosynthesis of LTB4 and LTC4.