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

Base Information

• Chemical Name: methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate
• CAS No.: 73466-12-3
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• DSSTox Substance ID: DTXSID10424293
• Nikkaji Number: J524.709H
• Wikidata: Q82236810
• Mol file: 73466-12-3.mol

Synonyms:leukotriene A methyl ester;leukotriene A methyl ester, (2alpha,3beta(1E,3E,5Z,8Z))-(+-)-isomer;leukotriene A methyl ester, (2S-(2alpha,3beta(1E,3E,5Z,8Z)))-isomer;leukotriene A4 methyl ester;LTA4 ME;methyl-(11,12,14,15-(2)H4)-oxidoeicosatetraenoate

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

Chemical Property:

• PSA: 38.83000
• LogP: 5.29230
• Storage Temp.: −20°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

99%, ^*data from raw suppliers

Leukotriene A4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-36/37/38-48/20-51/53-62-65-67
• Safety Statements: 9-16-29-33-36/37-61-62

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC=CC1C(O1)CCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)OC
• Description: 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.
• Uses: LTA4 (Leukotriene A4 methyl ester) is an unstable intermediate in the biosynthesis of LTB4 and LTC4.

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

There total 94 articles about methyl 4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

<(Z)-3-nonenyl>triphenyl phosphonium tosylate (82393-41-7) + (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) → Leukotriene A4 methyl ester (73466-12-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/0040-4039(88)85316-4

Reference yield: 88.0%

(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) + Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide (73958-09-5) → Leukotriene A4 methyl ester (73466-12-3)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;

DOI:10.1016/S0040-4039(00)86776-3

Reference yield: 63.0%

<(3Z)-nonen-1-yl>triphenylphosphonium iodide (72297-07-5) + (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) → Leukotriene A4 methyl ester (73466-12-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

DOI:10.1002/1099-0690(200009)2000:17<2991::AID-EJOC2991>3.0.CO;2-H

upstream raw materials:

diazomethane

6-epi-Leukotriene A₄

<(3Z)-nonen-1-yl>triphenylphosphonium iodide

(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester

Downstream raw materials:

7Z,9E,11E,14Z-LTD₄ methyl ester

Leukotriene C₄ methyl ester

leukotriene E4

leukotriene D4

Refernces

• 1、 Corey, E. J.,Wright, Stephen W.,Matsuda, Seiichi P. T.. "Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate". . p. 1452 - 1455. Retrieved 2007/10/02.
• 2、 Lellouche, J. P.,Aubert, F.,Beaucourt, J. P.. "SYNTHESIS OF TETRADEUTERATED LTA4 METHYL ESTER". . p. 3069 - 3072. Retrieved 2007/10/02.