Useful marker of PGI2 biosynthesis
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6-keto Prostaglandin F1α

Item No. 15210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-6-oxo-prost-13E-en-1-oic acid
CAS Number
58962-34-8
Synonyms
  • 6-keto PGF1α
Molecular Formula
C20H34O6
Formula Weight
370.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 50 mg/mlEthanol: 16.6 mg/mlPBS (pH 7.2): 3.3 mg/ml
SMILES
O[C@@H]1[C@H](CC(CCCCC(O)=O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1
InChi Key
KFGOFTHODYBSGM-ZUNNJUQCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    6-keto Prostaglandin F1α (6-keto PGF1α) is the inactive, non-enzymatic hydrolysis product of PGI2.1,2 6-keto PGF1α serves as a useful marker of PGI2 biosynthesis in vivo.3 When [3H]-PGI2 is injected into healthy human males, 6.6% of the radioactivity is recovered from urine as [3H]-6-keto PGF1α.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pace-Asciak, C.R. Isolation, structure, and biosynthesis of 6-ketoprostaglandin F1α in the rat stomach. J. Am. Chem. Soc. 98(8), 2348-2349 (1976).

    2. Johnson, R.A., Morton, D.R., Kinner, J.H., et al. The chemical structure of prostaglandin X (prostacyclin). Prostaglandins 12(6), 915-928 (1976).

    3. Brash, A.R., Jackson, E.K., Saggese, C.A., et al. Metabolic disposition of prostacyclin in humans. J. Pharmacol. Exp. Ther. 226(1), 78-87 (1983).

    Product Citations

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Archambault, A.-S., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (2022).

    Gurusamy, M., Nasseri, S., Rampa, D.R., et al. Inhibition of microsomal prostaglandin E synthase-1 ameliorates acute lung injury in mice. J. Transl. Med. 19(1), 340 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    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).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    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).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).