A racemic mixture of EPA derivatives
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(±)9-HEPE

Item No. 32400

Technical Information
Formal Name
(±)-9-hydroxy-5Z,7E,11Z,14Z,17Z-eicosapentaenoic acid
CAS Number
286390-03-2
Molecular Formula
C20H30O3
Formula Weight
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
235 nm
SMILES
CC/C=C\C/C=C\C/C=C\CC(O)\C=C\C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,17,19,21H,2,5,8,12,15-16,18H2,1H3,(H,22,23)/b4-3-,7-6-,11-9-,13-10-,17-14+
InChi Key
OXOPDAZWPWFJEW-IMCWFPBLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    (±)9-HEPE is a racemic mixture of the monohydroxy fatty acids 9(R)-HEPE and 9(S)-HEPE (Item No. 32410). It is produced by non-enzymatic oxidation of eicosapentaenoic acid (EPA; Item Nos. 90110 | 21908 | 90110.1).1 (±)9-HEPE (128 µM) induces peroxisome proliferator-activated receptor α (PPARα), PPARγ, and PPARδ transactivation in NIH3T3 cells expressing the mouse receptors.2 It reduces increases in the expression of the genes encoding inducible nitric oxide synthase (iNOS), TNF-α, IL-1β, and IL-6 in isolated mouse peritoneal macrophages induced by palmitate, as well as inhibits palmitate-induced migration of isolated mouse peritoneal macrophages, when used at a concentration of 1 µM.3 (±)9-HEPE decreases hepatic triglyceride levels and plasma LDL-cholesterol and total cholesterol levels in a mouse model of high-fat diet-induced hepatic steatosis when administered in combination with (±)5-HEPE (Item No. 32200) and (±)17,18-EEQ ((±)17(18)-EpETE; Item No. 50861).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fischer, R., Konkel, A., Mehling, H., et alDietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J. Lipid Res. 55(6), 1150-1164 (2014).

    2. Yamada, H., Oshiro, E., Kikuchi, S., et alHydroxyeicosapentaenoic acids from the Pacific krill show high ligand activities for PPARs. J. Lipid Res. 55(5), 895-904 (2014).

    3. Wang, C., Liu, W., Yao, L., et alHydroxyeicosapentaenoic acids and epoxyeicosatetraenoic acids attenuate early occurrence of nonalcoholic fatty liver disease. Br. J. Pharmacol. 174(14), 2358-2372 (2017).