A clickable form of EPA
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Eicosapentaenoic Acid Alkyne

Item No. 16704

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z,17Z-eicosapentaen-19-ynoic acid
Synonyms
  • Click Tag™ EPA Alkyne
  • EPA Alkyne
  • FA 20:7
Molecular Formula
C20H26O2
Formula Weight
298.4
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.15M Tris-HCl pH 8.5: >1 mg/mlDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): <100 µg/ml
SMILES
C#C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h1,3-4,6-7,9-10,12-13,15-16H,5,8,11,14,17-19H2,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChi Key
FCLMKCFLVGHPHY-JLNKQSITSA-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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    100 µg

    $260

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    500 µg

    $912

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    1 mg

    $1,548

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    Product Description

    Eicosapentaenoic acid (EPA; Item No. 90110) is an ω-3 fatty acid abundantly available in marine organisms that has been shown to offer anti-inflammatory and cardiovascular benefits.1,2 EPA alkyne is a form of EPA with an ω-terminal alkyne. The terminal alkyne group can be used in click chemistry linking reactions to tag EPA with fluorescent or biotinylated labels for analysis of its metabolism and biological activity.3,4 Because the alkyne group is at the ω-terminus, this compound can be used to easily tag metabolites and derivatives.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yerram, N.R., Moore, S.A., and Spector, A.A. Eicosapentaenoic acid metabolism in brain microvessel endothelium: Effect on prostaglandin formation. J. Lipid Res. 30(11), 1747-1757 (1989).

    2. Takeuchi, H., Inoue, J., Yoshida, M., et al. Dietary effects of n-3 eicosapentaenoic acid on essential fatty acid-deficiency symptoms of rats. Agric. Biol. Chem. 53(12), 3225-3232 (1989).

    3. Kolb, H.C., and Sharpless, K.B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 8(24), 1128-1137 (2003).

    4. Lutz, J.-F., and Zarafshani, Z. Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry. Adv. Drug Deliv. Rev. 60(9), 958-970 (2008).