A metabolite of EPA
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Prostaglandin E3

Item No. 14990

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11α,15S-dihydroxy-9-oxo-prosta-5Z,13E,17Z-trien-1-oic acid
CAS Number
802-31-3
Synonyms
  • PGE3
Molecular Formula
C20H30O5
Formula Weight
350.5
Purity
≥98%
Formulation (Request formulation change)
A 500 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): >5 mg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)C/C=C\CC)[C@H](O)C1
InChi Code
InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChi Key
CBOMORHDRONZRN-QLOYDKTKSA-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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    50 µg

    $156

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    100 µg

    $294

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    500 µg

    $1,228

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    1 mg

    $2,149

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    Product Description

    Prostaglandin E3 (PGE3) is formed via the cyclooxygenase (COX) metabolism of eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908).1 In human ocular tissue, it comprises 2.4% of the COX products formed.1 When applied to the eyes of a rabbit, a 1 µg dose of PGE3 decreases intraocular pressure from 21 mmHg to about 17 mmHg.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kulkarni, P.S., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in human and rabbit anterior uvea. Prostaglandins 31(6), 1159-1164 (1986).

    2. Kulkarni, P.S., and Srinivasan, B.D. Prostaglandins E3 and D3 lower intraocular pressure. Invest. Ophthalmol. Vis. Sci. 26(8), 1178-1182 (1985).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    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).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).