An internal standard for the quantification of 12(13)-EpOME
Related Products
Unlabeled Version(s)
52450(±)12(13)-EpOME
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

(±)12(13)-EpOME-d4

Item No. 10009996

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(12S,13R)-epoxy-9Z-octadecenoic-9,10,12,13-d4 acid
Synonyms
  • (±)12,13-EODE-d4
  • Isoleukotoxin-d4
  • (±)-Vernolic Acid-d4
Molecular Formula
C18H28D4O3
Formula Weight
300.5
Purity
≥99% deuterated forms (d1-d4)
Formulation
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@]1([2H])[C@](O1)([2H])C/C([2H])=C([2H])\CCCCCCCC(O)=O.CCCCC[C@@]2([2H])[C@@](O2)([2H])C/C([2H])=C([2H])\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/i2*8D,11D,16D,17D
InChi Key
FZJNHLHQUSTCNM-BVNPOWJLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    25 µg

    $123

    Add

    50 µg

    $231

    Add

    100 µg

    $435

    Add

    250 µg

    $962

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    (±)12(13)-EpOME-d4 is intended for use as an internal standard for the quantification of 12(13)-EpOME by GC- or LC-MS. 12(13)-EpOME is an epoxide formed primarily via metabolism of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) by the cytochrome P450 (CYP) isoforms CYP2J2, CYP2C8, and CYP2C9, however, CYP1A1 can contribute to 12(13)-EpOME production when pharmacologically induced.1 12(S),13(R)-EpOME and 12(R),13(S)-EpOME are produced at equal proportions from linoleic acid by peroxygenase, whereas CYP450-mediated metabolism of linoleic acid exclusively produces 12(S),13(R)-EpOME, in E. lagascae microsomes.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Blee, E., Ståhl, U., Schuber, F., et al. Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae. Biochem. Biophys. Res. Commun. 197(2), 778-784 (1993).

    Product Citations

    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).