An internal standard for the quantification of PGF2α ethanolamide
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Unlabeled Version(s)
16013Prostaglandin F2α Ethanolamide
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Prostaglandin F2α Ethanolamide-d4

Item No. 316013

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-9α,11α,15S-trihydroxy-prosta-5Z,13E-dien-1-amide-3,3,4,4-d4
Synonyms
  • Dinoprost Ethanolamide-d4
  • PGF2α-EA-d4
Molecular Formula
C22H35D4NO5
Formula Weight
401.6
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: MiscibleDMSO: 10 mg/mlEthanol: MisciblePBS (pH 7.2): 10 mg/ml
SMILES
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\C([2H])([2H])C([2H])([2H])CC(NCCO)=O
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/i5D2,8D2
InChi Key
XCVCLIRZZCGEMU-BREJCMGSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 µg

    $81

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    50 µg

    $152

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    100 µg

    $285

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    Product Description

    Prostaglandin F2α ethanolamide (PGF2α-EA-d4) contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of PGF2α-EA by GC- or LC-mass spectrometry. PGF2α-EA is produced by cyclooxygenase 2 (COX-2) metabolism of the endogenous cannabinoid arachidonoyl ethanolamide (AEA) found in brain, liver, and other mammalian tissues.1 AEA can be metabolized by fatty acid amide hydrolase (FAAH) to give free arachidonic acid, which is the well known and conventional substrate for COX enzymes. However, it has also been reported that AEA can be used directly by COX-2 to produce ethanolamide congeners of the classical prostaglandins, including PGE2.2 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.3

    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. 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).