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Fatty Acids Attached to All-Trans-Astaxanthin Alter Its Cis-Trans Equilibrium, and Consequently Its Stability, Upon Light-Accelerated Autoxidation

Fatty Acids Attached to All-Trans-Astaxanthin Alter Its Cis-Trans Equilibrium, and Consequently Its Stability, Upon Light-Accelerated Autoxidation

Wouter J C de Bruijn, Yannick Weesepoel, Jean-Paul Vincken, Harry Gruppen

Food Chem. 2016 Mar 1;194:1108-15.

PMID: 26471660

Abstract:

Fatty acid esterification, common in naturally occurring astaxanthin, has been suggested to influence both colour stability and degradation of all-trans-astaxanthin. Therefore, astaxanthin stability was studied as influenced by monoesterification and diesterification with palmitate. Increased esterification decelerated degradation of all-trans-astaxanthin (RP-UHPLC-PDA), whereas, it had no influence on colour loss over time (spectrophotometry). This difference might be explained by the observation that palmitate esterification influenced the cis-trans equilibrium. Free astaxanthin produced larger amounts of 9-cis isomer whereas monopalmitate esterification resulted in increased 13-cis isomerization. The molar ratios of 9-cis:13-cis after 60min were 1:1.7 (free), 1:4.8 (monopalmitate) and 1:2.6 (dipalmitate). The formation of 9-cis astaxanthin, with its higher molar extinction coefficient than that of all-trans-astaxanthin, might compensate for colour loss induced by conjugated double bond cleavage. As such, it was concluded that spectrophotometry is not an accurate measure of the degradation of the all-trans-astaxanthin molecule.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP113085044	9-cis-Astaxanthin		113085-04-4	Price
AP472617-A	all-trans-Astaxanthin		472-61-7	Price

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