A prodrug formulation of HPA
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Heneicosapentaenoic Acid methyl ester

Item No. 11622

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6Z,9Z,12Z,15Z,18Z-heneicosapentaenoic acid, methyl ester
CAS Number
65919-53-1
Synonyms
  • HPA methyl ester
  • SFE 22:5
Molecular Formula
C22H34O2
Formula Weight
330.5
Purity
≥98%
Formulation
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.15 M Tris-HCl pH 8.5: >1 mg/ml (from Oleic Acid)DMF: >100 mg/ml (from Oleic Acid)DMSO: >100 mg/ml (from Oleic Acid)Ethanol: >100 mg/ml (from Oleic Acid)PBS (pH 7.2): <100 µg/ml (from Oleic Acid)
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(OC)=O
InChi Code
InChI=1S/C22H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-2/h4-5,7-8,10-11,13-14,16-17H,3,6,9,12,15,18-21H2,1-2H3/b5-4-,8-7-,11-10-,14-13-,17-16-
InChi Key
VWHAHPVYEMPWTO-JEBPEJKESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $119

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    5 mg

    $525

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    10 mg

    $930

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    Product Description

    Heneicosapentaenoic Acid (HPA) is a fatty acid present in trace amounts in the green algae Bryopsis pennata Lamouroux and in fish oils. Its chemical composition is similar to eicosapentaenoic acid (EPA) except elongated with one carbon on the carboxyl end, placing the first double bond in the Δ6 position.1 HPA can be used to study the significance of the position of the double bonds in n-3 fatty acids. It incorporates into phospholipids and into triacylglycerol in vivo with the same efficiency as EPA and docosahexaenoic acid (DHA) and exhibits strong inhibition of arachidonic acid synthesis from linoleic acid.1 HPA is a poor substrate for prostaglandin H (PGH) synthase and for 5-lipoxygenase but retains the ability to rapidly inactivate PGH synthase.1 In certain formulations, HPA methyl ester may serve as a prodrug, which should facilitate uptake of HPA and then be hydrolyzed by esterases to generate the free acid once incorporated into cells. It may also be useful as a reference standard in analytical work.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Larsen, L.N., Hovik, K., Bremer, J., et al. Heneicosapentaenoate (21:5n-3): Its incorporation into lipids and its effects on arachidonic acid and eicosanoid synthesis. Lipids 32(7), 707-714 (1997).

    Product Citations

    Zhang, L.J., Salekeen, R., Soto-Palma, C., et al. Article polyunsaturated lipid senolytics exploit a ferroptotic vulnerability in senescent cells. Cell Press Blue 1(1), 100004 (2026).