Naturally occurring poly-cis carotenoids. Stereochemistry of poly-cis lycopene and its congeners in ‘Tangerine’ tomato fruits

Abstract

Spectroscopic data and comparison with synthetic model compounds establish that the carotenoid pigments phytoene, phytofluene, ζ-carotene, neurosporene, and lycopene found in the Tangerine tomato fruit have the sterochemistries C-15-mono-cis(1), C-15, C-9′-di-cis(2), C-9, C-9′-di-cis(3), C-9,C-9′,C-7′-tri-cis(4), and C-7,C-9,C-9′,C-7′-tetra-cis(5), respectively; the remaining double bonds in the pigments have the trans-geometry.