A stable, hydrolyzable derivative of (±)5(6)-EET
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Labeled Version(s)
29382(±)5(6)-EET-d11 methyl ester
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(±)5(6)-EET methyl ester

Item No. 50210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(5S,6R)-epoxy-8Z,11Z,14Z-eicosatrienoic acid, methyl ester
Synonyms
  • (±)5,6-EpETrE methyl ester
Molecular Formula
C21H34O3
Formula Weight
334.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
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=C\C/C=C\C[C@@H](O1)[C@@H]1CCCC(OC)=O.CCCCC/C=C\C/C=C\C/C=C\C[C@H](O2)[C@H]2CCCC(OC)=O
InChi Code
InChI=1S/2C21H34O3/c2*1-3-4-5-6-7-8-9-10-11-12-13-14-16-19-20(24-19)17-15-18-21(22)23-2/h2*7-8,10-11,13-14,19-20H,3-6,9,12,15-18H2,1-2H3/b2*8-7-,11-10-,14-13-/t19-,20+;19-,20-/m00/s1
InChi Key
KVFMFIQDGYIWEI-GIPIVLEDSA-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

    $90

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    100 µg

    $156

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    250 µg

    $291

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    Product Description

    (±)5(6)-EET (Item No. 50211) is biosynthesized in rat and rabbit liver microsomes by CYP450.1,2 In neuroendocrine cells, such as the anterior pituitary and pancreatic islet, (±)5(6)-EET has been implicated in the mobilization of Ca2+ and hormone secretion.3,4 Since (±)5(6)-EET is highly unstable, (±)5(6)-EET methyl ester is used for bulk storage and small amounts converted to the free acid just before use.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982).

    2. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. The Journal of Biological Chemisty 257(7), 3771-3781 (1982).

    3. Snyder, C., Lattanzio, F., Yadagiri, P., et al. 5,6-Epoxyeicosatrienoic acid mobilizes Ca2+ in anterior pituitary cells. Biochem. Biophys. Res. Commun. 139(3), 1188-1194 (1986).

    4. Falck, J.R., Manna, S., Moltz, J., et al. Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets. Biochem. Biophys. Res. Commun. 114(2), 743-749 (1983).