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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:
73466-12-3
Molecular Weight:
332.48
MDL number:
MFCD00065847
UNSPSC Code:
12352211
PubChem Substance ID:
24896396

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
B Mannervik et al.
FEBS letters, 175(2), 289-293 (1984-10-01)
Six major basic cytosolic glutathione transferases from rat liver catalyzed the conversion of leukotriene A4 methyl ester to the corresponding leukotriene C4 monomethyl ester. Glutathione transferase 4-4, the most active among these enzymes, had a Vmax of 615 nmol X
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
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