cis-Parinaric Acid

cis-Parinaric Acid

Cayman Chemical Item Number 71430

α-Parinaric Acid (CAS 18427-44-6)

cis-Parinaric Acid (CAS 18427-44-6)

Description

cis-Parinaric acid is a naturally occurring polyunsaturated fatty acid containing an unusual conjugated (Z,E,E,Z) tetraene. This chromophore provides for a natural fluorescence at 432 nm with an excitation wavelength at 320 nm. cis-Parinaric acid occurs naturally in the seeds of the Makita tree, a tropical rainforest tree indigenous to Fiji. Makita seeds are inedible, and this toxicity may be due at least in part to the unstable conjugated fatty acids, including cis-parinaric acid, contained within the seed. cis-Parinaric acid has been used for the measurement of phospholipase activity, lipase activity, and as an indicator of lipid peroxidation.^1,2,3,4

1 Wolf, C., Sagaert, L., and Bereziat, G. A sensitive assay of phospholipase using the fluorescent probe 2-parinaroyllecithin. Biochem Biophys Res Commun 99 275-283 (1981).

2 Beisson, F., Ferté, N., Nari, J., et al. Use of naturally fluorescent triacylglycerols from Parinari glaberrimum to detect low lipase activities from Arabidopsis thaliana seedlings. J Lipid Res 40 2313-2321 (1999).

3 McGuire, S.O., James-Kracke, M.R., Sun, G.Y., et al. An esterification protocol for cis-parinaric acid-determined lipid peroxidation in immune cells. Lipids 32 219-226 (1997).

4 de Hingh, Y.C.M., Meyer, J., Fischer, J.C., et al. Direct measurement of lipid peroxidation in submitochondrial particles. Biochemistry 34 12755-12760 (1995).

Synonyms

α-Parinaric Acid

Formal Name

9Z,11E,13E,15Z-octadecatetraenoic acid

CAS Number

18427-44-6

Molecular Formula

C₁₈H₂₈O₂

Formula Weight

276.4

Formulation

A crystalline solid

Purity

>98% (may contain up to 5% trans-Parinaric acid)

λ_max

292, 305, 319 nm

Stability

2 years

Storage

-80°C

Shipping

Dry ice in continental US; may vary elsewhere

SMILES

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CC/C=C\C=C/C=C\C=C\CCCCCCCC(=O)O

Background Reading

de Hingh, Y.C.M., Meyer, J., Fischer, J.C., et al. Direct measurement of lipid peroxidation in submitochondrial particles. Biochemistry 34 12755-12760 (1995).

McGuire, S.O., James-Kracke, M.R., Sun, G.Y., et al. An esterification protocol for cis-parinaric acid-determined lipid peroxidation in immune cells. Lipids 32 219-226 (1997).

Beisson, F., Ferté, N., Nari, J., et al. Use of naturally fluorescent triacylglycerols from Parinari glaberrimum to detect low lipase activities from Arabidopsis thaliana seedlings. J Lipid Res 40 2313-2321 (1999).

Wolf, C., Sagaert, L., and Bereziat, G. A sensitive assay of phospholipase using the fluorescent probe 2-parinaroyllecithin. Biochem Biophys Res Commun 99 275-283 (1981).

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