A metabolite of AEA
Related Products
Labeled Version(s)
316013Prostaglandin F2α Ethanolamide-d4
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Prostaglandin F2α Ethanolamide

Item No. 16013

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-N-(2-hydroxyethyl)-prosta-5Z,13E-dien-1-amide
CAS Number
353787-70-9
Synonyms
  • Dinoprost Ethanolamide
  • PGF2α-EA
Molecular Formula
C22H39NO5
Formula Weight
397.5
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: MiscibleDMSO: 10 mg/mlEthanol: MisciblePBS (pH 7.2): 10 mg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(NCCO)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C22H39NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-,21+/m0/s1
InChi Key
XCVCLIRZZCGEMU-WLOFLUCMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

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

    1 mg

    $79

    Add

    5 mg

    $345

    Add

    10 mg

    $610

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Prostaglandin F2α ethanolamide (PGF2α-EA) is produced by COX-2 metabolism of the endogenous cannabinoid, arachidonoyl ethanolamide (AEA), found in brain, liver, and other mammalian tissues.1 AEA can be metabolized directly by the sequential action of COX-2 and specific PG synthases to produce ethanolamide congeners of the classical PGs.2,3 PGF2α-EA has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of living mice. PGF2α-EA is a potent dilator (EC50 = 58 nM) of the cat iris sphincter, which is a model system for testing potential intraocular hypotensive agents.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bachur, N.R., Masek, K., Melmon, K.L., et al. Fatty acid amides of ethanolamine in mammalian tissues. The Journal of Biological Chemisty 240, 1019-1024 (1965).

    2. Yu, M., Ives, D., and Ramesha, C.S. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. The Journal of Biological Chemisty 272(34), 21181-21186 (1997).

    3. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).

    4. Woodward, D.F., Tang-Liu, D.D.S., Madhu, C., et al. Prostaglandin F2α (PGF2α) 1-ethanolamide: A pharmacologically unique local hormone biosynthesized from anandamide. 11th International conference on advances in prostaglandin and leukotriene research: Basic science and new clinical applications 27 (2000).

    Product Citations

    Richie-Jannetta, R., Nirodi, C.S., Crews, B.C., et al. Structural determinants for calcium mobilization by prostaglandin E2 and prostaglandin F2α glyceryl esters in RAW 264.7 cells and H1819 cells. Prostaglandins Other Lipid Mediat. 92(1-4), 19-24 (2010).