methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate

HCID 6478221CAS 73466-12-3

Substructure search Find similar structures

Basic information

Standard SMILES: CCCCC/C=C\C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(=O)OC
InChIKey: WTKAVFHPLJFCMZ-NIBLXIPLSA-N
Molecular formula: C21H32O3
Average molar mass: 332.5 g/mol
Monoisotopic mass: 332.23514488

Names & identifiers

Preferred name: methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate
IUPAC: methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate
English name: (-)-Leukotriene A4 methyl ester
Molecular formula: C21H32O3
Molecular weight: 332.48

Names & synonyms

73466-12-3LTA4-methyl estermethyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoateLTA4 (Leukotriene A4 methyl ester)(-)-LEUKOTRIENEA4METHYLESTER(-)-Leukotriene A4 methyl ester72345-92-7LTA4 methyl ester(+/-)-Leukotriene A4 methyl esterMFCD00065847orb1984949SCHEMBL29620680

Show more names

(-)-leukotriene A4LEUKOTRIENE A4 METHYL ESTERPWXYNAKNLZUYAL-WAQVJNLQSA-N5S-TRANS-5,6-OXIDO-7E,9E,11Z,14Z-EICOSATETRAENOIC ACID, METHYL ESTERLEUKOTRIENE A4-METHYLESTER SOLUTION (100UG/ML HEXANE/1% TRIETHYLAMINE)14,15-Leukotriene A4 methyl ester, Inhibitor of Leukotriene A4 hydrolaseLeukotriene A4 methyl ester, Leukotriene B3 and Leukotriene B4 precursor2-Oxiranebutanoic acid, 3-(1E,3E,5Z,8Z)-1,3,5,8-tetradecatetraen-1-yl-, methyl ester, (2S,3S)-

DTXSID10424293WTKAVFHPLJFCMZ-NIBLXIPLSA-NAKOS040755937FL165279HY-112621CS-0058562T37616SR-01000946885

Database identifiers

CAS: 73466-12-3、72345-92-7
PubChem CID: 6478221
DTXSID: DTXSID10424293
EC Number: 633-240-5
Nikkaji: J524.709H

Properties

Computed structural properties

XLogP: 5.6
Topological polar surface area: 38.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 14
Heavy atoms: 24
Formal charge: 0
Complexity: 446

Physicochemical properties

Boiling point: 442.453 · 442.453±25.00 °C(Press: 760.00 Torr)(predicted)
Density: 0.998 · 0.998±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
storage temp.: 20 °C · −20°C
solubility: 50 mg/ml; · Acetone: >50 mg/ml; DMF: >50 mg/ml; DMSO: >50 mg/ml; Ethanol: >50 mg/ml; PBS pH 7.2: insoluble and unstable.
form: triethylamine:hexane solution
FDA UNII: 7 Y7MPZ6563 · 7Y7MPZ6563
UNSPSC Code: 12352211 · 12352211
NACRES: 25 · NA.25
Symbol(GHS): 2 · GHS02,GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 225 · H225-H315-H319-H361-H336-H373-H304-H411
Precautionary statements: 201 · P201-P202-P210-P240-P241-P242-P243-P260-P264-P271-P273-P280-P301+P310-P321-P331-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P314-P362+P364-P332+P313-P337+P313-P370+P378-P391-P403+P233-P403+P235-P405-P501
target organs: Central nervous system, Nervous system, Respiratory system
Hazard Codes: F,Xn,N
Risk Statements: 11 · 11-36/37/38-48/20-51/53-62-65-67
Safety Statements: 9 · 9-16-29-33-36/37-61-62
RIDADR: 1208 · UN 1208 3/PG 2
WGK Germany: 2 · 2
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Asp · Aquatic Chronic 2Asp. Tox. 1Eye Irrit. 2Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 1 InhalationSTOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (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 information

Hazard Classes and CategoriesFlam. Liq. 2 (100%)

Safety data

wgk: 2
ridadr: UN 1208 3/PG 2
risk_code: 11-36/37/38-48/20-51/53-62-65-67
Signal word: Danger
Symbol(GHS): GHS02,GHS07,GHS08,GHS09
hazard_code: F,Xn,N
safety_code: 9-16-29-33-36/37-61-62
Storage Class: 3 - Flammable liquids
target organs: Central nervous system, Nervous system, Respiratory system
Hazard statements: H225-H315-H319-H361-H336-H373-H304-H411
Hazard Classifications: Aquatic Chronic 2Asp. Tox. 1Eye Irrit. 2Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 1 InhalationSTOT SE 3
Precautionary statements: P201-P202-P210-P240-P241-P242-P243-P260-P264-P271-P273-P280-P301+P310-P321-P331-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P314-P362+P364-P332+P313-P337+P313-P370+P378-P391-P403+P233-P403+P235-P405-P501

Chemistry & industry

Applications · 2 items

DescriptionLeukotriene 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.

UsesLTA4 (Leukotriene A4 methyl ester) is an unstable intermediate in the biosynthesis of LTB4 and LTC4.