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Investigating carotenoid loss after drying and storage of

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36<br />

1. Literature review<br />

Two types <strong>of</strong> asymmetric cleavage <strong>of</strong> trans-"-carotene, 7’-8’ <strong>and</strong> 9’-10’, lead to the<br />

formation <strong>of</strong> "-cyclocitral <strong>and</strong> "-apo-8’carotenal; "-ionone <strong>and</strong> "-apo-10’carotenal<br />

respectively (Figure 1-20).<br />

-<br />

Trans-β-carotene<br />

+<br />

β-apo-8’-carotenal β-cyclocitral<br />

+<br />

β-apo-10’-carotenal β-ionone<br />

Figure 1-20: 7’-8’ <strong>and</strong> 9’-10’cleavage <strong>of</strong> !-carotene <strong>and</strong> formation <strong>of</strong> 5,6 epoxy-!ionone<br />

<strong>and</strong> dihydroactinidiolide (DHA) from !-ionone. Mordi et al. (1993); Waché<br />

et al. (2003).<br />

The cleavages can arise from autoxidation (Mordi et al. 1993) or enzymatic reactions<br />

(Waché et al. 2003). Epoxidation <strong>of</strong> "-ionone into 5,6 epoxy-"-ionone <strong>and</strong> thermal<br />

rearrangement <strong>of</strong> 5,6 epoxy-"-ionone into dihydroactinidiolide (DHA) has been<br />

previously described (Mordi et al. 1993; Waché et al. 2003) (Figure 1-20).<br />

Norisoprenoids formed <strong>after</strong> oxidation <strong>of</strong> β-carotene include β-ionone (fragrance <strong>of</strong><br />

roses), 5,6-epoxy-β-ionone, β-cyclocitral (flower fragrance with fruit tones), limonene<br />

(odour <strong>of</strong> oranges), DHA (sweet, tea-like odour). These compounds are used in<br />

perfumery. The production <strong>of</strong> aromas from <strong>carotenoid</strong>s has also been widely studied.

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