A COX product of EPA
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Prostaglandin F3α

Item No. 16990

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-prosta-5Z,13E,17Z-trien-1-oic acid
CAS Number
745-64-2
Synonyms
  • PGF3α
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥98%
Formulation
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
10 mM Na2CO3: >6.5 mg/ml (from PGF2a)DMF: >100 mg/ml (from PGF2a)DMSO: >100 mg/ml (from PGF2a)Ethanol: >100 mg/ml (from PGF2a)PBS pH 7.2: >10 mg/ml (from PGF2a)
SMILES
O[C@@H]1[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/C20H32O5/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/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChi Key
SAKGBZWJAIABSY-SAMSIYEGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 µg

    $81

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    100 µg

    $145

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    500 µg

    $643

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    1 mg

    $1,044

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    Product Description

    Prostaglandin F3α (PGF3α) is a COX product of EPA. The biosynthesis of PGF3α from EPA was demonstrated in vitro in human and rabbit ocular tissues.1 It has only 25% affinity at the ovine luteal FP receptor compared to PGF2α.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. Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem. Pharmacol. 38(14), 2375-2381 (1989).

    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).

    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).

    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).