Formation of Carotenoid Oxygenated Cleavage Products - Carotenoids: Physical, Chemical, and Biological Functions and Properties - page 215

11

Formation of Carotenoid
Oxygenated Cleavage
Products

Catherine Caris-Veyrat

CONTENTS
11.1 Introduction .......................................................................................................................... 215
11.2 Occurrence in Nature and Formation in Biochemical Systems ........................................... 216
11.3 Formation by Autoxidation in Model Systems ..................................................................... 217
11.4 Formation by Chemical Oxidation ....................................................................................... 219
11.5 Formation during Food Processing or Model Food Systems ............................................... 224
11.6 Conclusions........................................................................................................................... 225
Acknowledgments .......................................................................................................................... 225
References ...................................................................................................................................... 225

11.1 INTRODUC TION
Molecules formed from carotenoids are given different names in the literature, for instance,
carotenoid-derived products, degraded carotenoids (Walberg and Eklund 1998), carotenoid decom-
position products (Wang 2004), carotenoid oxidation products, carotenoid oxidative/degradative
products (Wang 2004), carotenoid oxidative breakdown products (Bonnie and Choo 1999), oxida-
tive cleavage products, apocarotenoids, and lycopenoids (Lindshield et al. 2007). The use of each
term is justii ed in the relevant context of each cited article, making it very difi cult or even impos-
sible to choose one of these terms for general use.
In this chapter, we focus on a category of molecules obtained from carotenoids in which at
least one of the carbon-carbon bonds has been cleaved and at least one oxygen atom has been
introduced. These products are referred to as carotenoid oxygenated cleavage products. According
to the accepted rules of carotenoid nomenclature (Weedon and Moss 1995), “derivatives in which
the carbon skeleton has been shortened by the formal removal of fragments from one end or both
ends of a carotenoid” are called, respectively, apo- or diapocarotenoids. When i ssion occurs on
a cyclic bond, the C40 carbon skeleton is retained, and the products are called seco-carotenoids.
In most cases, the organic functional group replacing the lost end of the carotenoid contains at
least one oxygen atom and is often an alcohol, aldehyde, ketone, carboxylic acid, or ester function
(Figure 11.1). Like apocarotenoids, norcarotenoids have fewer than 40 carbon atoms. However,
those that have been eliminated come from within the carotenoid skeleton, and, as such, they do not
i t our dei nition of cleavage compounds. Two types of oxygenated cleavage products of carotenoids
can be distinguished: volatiles and nonvolatiles. We concentrate our review on nonvolatile products,
mentioning studies on volatile compounds either when nonvolatiles have been studied at the same
time or when the effects of food thermal processing on carotenoids are described.

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