The 9,10-cis epoxide of linoleic acid
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Labeled Version(s)
10009995(±)9(10)-EpOME-d4
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(±)9(10)-EpOME

Item No. 52400

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(9R,10S)-epoxy-12Z-octadecenoic acid
Synonyms
  • Coronaric Acid
  • (±)9,10-EODE
  • Leukotoxin
Molecular Formula
C18H32O3
Formula Weight
296.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 1 mg/ml
SMILES
CCCCC/C=C\C[C@@H](O1)[C@@H]1CCCCCCCC(O)=O.CCCCC/C=C\C[C@H](O2)[C@H]2CCCCCCCC(O)=O
InChi Code
InChI=1S/2C18H32O3/c2*1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h2*7,10,16-17H,2-6,8-9,11-15H2,1H3,(H,19,20)/b2*10-7-/t2*16-,17+/m10/s1
InChi Key
CQGSTFOWRAHVDF-ZZGFUMFISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $83

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    50 µg

    $141

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    100 µg

    $248

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    250 µg

    $413

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    Product Description

    (±)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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hayakawa, M., Sugiyama, S., Takamura, T., et al. Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoate. Biochem. Biophys. Res. Commun. 137(1), 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(3), 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(2), 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(1), 53-59 (1997).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).