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L5140

Sigma-Aldrich

(−)-Leukotriene A4 methyl ester

~98%, triethylamine:hexane solution

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About This Item

Empirical Formula (Hill Notation):
C21H32O3
CAS Number:
Molecular Weight:
332.48
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:

assay

~98%

form

triethylamine:hexane solution

functional group

ester

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)OC

InChI

1S/C21H32O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-19-20(24-19)17-15-18-21(22)23-2/h7-8,10-14,16,19-20H,3-6,9,15,17-18H2,1-2H3/b8-7-,11-10-,13-12+,16-14+/t19-,20-/m0/s1

InChI key

WTKAVFHPLJFCMZ-NIBLXIPLSA-N

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Biochem/physiol Actions

Precursor of leukotriene C4.

Packaging

Packaged under argon

Caution

Free acid is unstable; hydrolysis is not recommended.

Physical form

Solution in triethylamine: hexane (2:98)

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


Certificates of Analysis (COA)

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M Söderström et al.
The Biochemical journal, 250(3), 713-718 (1988-03-15)
Leukotriene C4 synthesis was studied in preparations from mouse mastocytoma cells. Enzymic conjugation of leukotriene A4 with glutathione was catalysed by both the cytosol and the microsomal fraction. The specific activity of the microsomal fraction (7.8 nmol/min per mg of
Preparation of tetradeuterated leukotriene A4 methyl ester: methyl-[11,12,14,15-2H4]-(5S,6S)-oxido-(7E,9E,11Z, 14Z)-eicosatetraenoat e.
J P Lellouche et al.
Methods in enzymology, 187, 70-76 (1990-01-01)
C Prakash et al.
Prostaglandins, 37(2), 251-258 (1989-02-01)
C-20 Trideuterated leukotriene A4 methyl ester was prepared by Wittig condensation of a deuterated C9-phosphonium salt with a C11-epoxydienal. It was then treated separately with glutathione, cysteinylglycine and cysteine. The resulting esters were saponified to give C-20 trideuterated leukotrienes C4
Shimizu, T., et al.
Proceedings of the National Academy of Sciences of the USA, 81, 689-689 (1987)
G Maury et al.
Biochemistry international, 15(6), 1127-1135 (1987-12-01)
It has been shown that various glutathione transferases can synthesize leukotriene C4, or its methyl ester, from glutathione and leukotriene A4. We questioned whether the same enzymes could be used to resolve racemic leukotriene A4 methyl ester (more easily prepared

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