An active metabolite of EPA
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5(S)-HEPE

Item No. 32210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
CAS Number
92008-51-0
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
236 nm
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C=C/[C@@H](O)CCCC(=O)O
InChi Code
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChi Key
FTAGQROYQYQRHF-GHWNLOBHSA-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

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

    $129

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    50 µg

    $245

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    100 µg

    $460

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    250 µg

    $1,016

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    Product Description

    5(S)-HEPE is an active metabolite of eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908).1 It is formed from EPA by 5-lipoxygenase (5-LO). 5(S)-HEPE is an agonist of G protein-coupled receptor 119 (GPR119).2 It increases cAMP accumulation in CHO-K1 cells expressing human GPR119 when used at a concentration of 10 µM. 5(S)-HEPE increases glucose-induced insulin secretion from MING6 insulinoma pancreatic islets and glucagon-like peptide 1 (GLP-1) secretion from HuTu 80 adenocarcinoma cells when used at a concentration of 10 µM. Serum levels of 5(S)-HEPE are elevated in patients with hyperlipidemia.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Noguchi, N., Yoshida, Y., Kaneda, H., et al. Action of ebselen as an antioxidant against lipid peroxidation. Biochem. Pharmacol. 44(1), 39-44 (1992).

    2. Kogure, R., Toyama, K., Kiyamuta, S., et al. 5-Hydroxy-eicosapentaenoic acid is an endogenous GPR119 agonist and enhances glucose-dependent insulin secretion. Biochem. Biophys. Res. Commun. 416(1-2), 58-63 (2011).

    3. Schuchardt, J.P., Schmidt, S., Kressel, G., et al. Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men. Prostaglandins Leukot. Essent. Fatty Acids 89(1), 19-29 (2013).

    Product Citations

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    Kogure, R., Toyama, K., Kiyamuta, S., et al. 5-Hydroxy-eicosapentaenoic acid is an endogenous GPR119 agonist and enhances glucose-dependent insulin secretion. Biochem. Biophys. Res. Commun. 416(1-2), 58-63 (2011).