A metabolite of adrenic acid
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(±)13,14-EDT

Item No. 38937

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-12-[(2R,3S)-3-(2Z)-2-octen-1-yl-2-oxiranyl]-7Z,10Z-dodecadienoic acid
CAS Number
355016-19-2
Synonyms
  • (±)-Dihomo-13,14-EET
  • (±)13,14-EpDoTrE
  • (±)13,14-Epoxydocosatrienoic Acid
Molecular Formula
C22H36O3
Formula Weight
348.5
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 1 mg/ml
SMILES
OC(CCCCC/C=C\C/C=C\C[C@@H]1[C@@H](O1)C/C=C\CCCCC)=O
InChi Code
InChI=1S/C22H36O3/c1-2-3-4-5-11-14-17-20-21(25-20)18-15-12-9-7-6-8-10-13-16-19-22(23)24/h6-7,11-12,14-15,20-21H,2-5,8-10,13,16-19H2,1H3,(H,23,24)/b7-6-,14-11-,15-12-/t20-,21+/m0/s1
InChi Key
UVNNQFJWBKVIOH-GAJPIYPSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $55

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    50 µg

    $99

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    100 µg

    $189

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    500 µg

    $822

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    Product Description

    (±)13,14-EDT is an oxylipin and a metabolite of adrenic acid (Item No. 90300) formed via the cytochrome P450 (CYP) pathway.1,2 It activates large-conductance calcium-activated potassium channels (KCa1.1/BK) in isolated rat coronary small arterial smooth muscle cells when used at a concentration of 50 nM and induces dilation of isolated porcine arterioles (EC50 = 12 pM).3 (±)13,14-EDT also induces relaxation of isolated bovine coronary arteries precontracted with the TP receptor agonist U-46619 (Item No. 16450).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Singh, N., Barnych, B., Wagner, K.M., et al. Adrenic acid-derived epoxy fatty acids are naturally occurring lipids and their methyl ester prodrug reduces endoplasmic reticulum stress and inflammatory pain. ACS Omega 6(10), 7165-7174 (2021).

    2. Yi, X.-Y., Gauthier, K.M., Cui, L., et al. Metabolism of adrenic acid to vasodilatory 1α,1β-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries. Am. J. Physiol. Heart Circ. Physiol. 292(5), H2265-H2274 (2007).

    3. Zhang, Y., Oltman, C.L., Lu, T., et al. EET homologs potently dilate coronary microvessels and activate BKCa channels. Am. J. Physiol. Heart Circ. Physiol. 280(6), H2430-H2440 (2001).