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Cat. Number

652645743049887

Chemical Name

(±)9(10)-EpOME-d4

References

Synonyms	Leukotoxin-d4 9,10-EODE-d4
Formal Name	(±)9(10)epoxy-12Z-octadecenoic 9,10,12,13-d4 acid
Molecular Formula	C₁₈H₂₈D₄O₃
Formula Weight	300.5
Formulation	A solution in methyl acetate
Purity	≥99% deuterated product
Stability	1 year
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	CCCCCC(=C([2H])/C[C@@H]1([2H])O[C@@H]1([2H])CCCCCCCC(=O)O)[2H]

Background Reading

Kosaka, K., Suzuki, K., Hayakawa, M., et al. Leukotoxin, a linoleate epoxide: Its implication in the late death of patients with extensive burns. Mol Cell Biochem 139 141-148 (1994).

Hayakawa, M., Sugiyama, S., Takamura, T., et al. Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoate. Biochem Biophys Res Commun 137 424-430 (1986).

Ozawa, T., Hayakawa, M., Takamura, T., et al. Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia. Biochem Biophys Res Commun 134 1071-1078 (1986).

Moran, J.H., Weise, R., Schnellmann, R.G., et al. Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol Appl Pharmacol 146 53-59 (1997).

Show all 4 Hide all but first 3

Size	Global Purchasing
25 µg
50 µg
100 µg
250 mg

Description

(±)9,10-EpOME-d₄ contains four deuterium atoms at the 9, 10, 12, and 13 positions. It is intended for use as an internal standard for the quantification of latanoprost by GC- or LC-mass spectrometry (MS). (±)9(10)-EpOME is the 9,10-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst.¹ It has been recovered from the lungs of hyperoxic rats and from humans with acute respiratory distress syndrome.² Mitochondrial dysfunction is the main feature of (±)9(10)-EpOME cytotoxicity, which may be due to the diol metabolites as well as the parent epoxide.^3,4

1 Hayakawa, M., Sugiyama, S., Takamura, T., et al. Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoate. Biochem Biophys Res Commun 137 424-430 (1986).

2 Ozawa, T., Hayakawa, M., Takamura, T., et al. Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia. Biochem Biophys Res Commun 134 1071-1078 (1986).

3 Kosaka, K., Suzuki, K., Hayakawa, M., et al. Leukotoxin, a linoleate epoxide: Its implication in the late death of patients with extensive burns. Mol Cell Biochem 139 141-148 (1994).

4 Moran, J.H., Weise, R., Schnellmann, R.G., et al. Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol Appl Pharmacol 146 53-59 (1997).

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