The 12,13-cis epoxide form of linoleic acid
Related Products
Active Metabolite(s)
10009832(±)12(13)-DiHOME
Labeled Version(s)
10009996(±)12(13)-EpOME-d4
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(±)12(13)-EpOME

Item No. 52450

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(12S,13R)-epoxy-9Z-octadecenoic acid
Synonyms
  • (±)12,13-EODE
  • Isoleukotoxin
  • (±)-Vernolic Acid
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@@H]1[C@@H](O1)C/C=C\CCCCCCCC(O)=O.CCCCC[C@H]2[C@H](O2)C/C=C\CCCCCCCC(O)=O
InChi Code
InChI=1S/2C18H32O3/c2*1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h2*8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b2*11-8-/t2*16-,17+/m10/s1
InChi Key
FZJNHLHQUSTCNM-DCYRUHRZSA-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

    $50

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    50 µg

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    100 µg

    $159

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    250 µg

    $347

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    Product Description

    (±)12(13)-EpOME is the 12,13-cis epoxide form of linoleic acid (Item Nos. 90150 | 90150.1 | 21909).1,2 It is formed primarily via linoleic acid metabolism by the cytochrome P450 (CYP) isoforms CYP2J2, CYP2C8, and CYP2C9, however, CYP1A1 can contribute to (±)12(13)-EpOME production when pharmacologically induced.2 (±)12(13)-EpOME (500 µM) induces mitochondrial dysfunction and cell death in renal proximal tubule epithelial cells.

    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. Hildreth, K., Kodani, S.D., Hammock, B.D., et al. Cytochrome P450-derived linoleic acid metabolites EpOMEs and DiHOMEs: A review of recent studies. J. Nutr. Biochem. 19, 108484 (2020).

    Product Citations

    Bracken, O.V., Jalali, P., Glanville, J.R.W., et al. Epoxy-oxylipins direct monocyte fate in inflammatory resolution in humans. Nat. Commun. 17(1), 431 (2026).

    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).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).