The Stereochemistry of Dehydro-β-Carotene. Studies on the Interaction of Some Carotenoids with Boron Trifluoride and N-Bromosuccinimide. Provitamin A Activity of a C₄₂-Carotenoid

Citation

Wallcave, Lawrence (1953) The Stereochemistry of Dehydro-β-Carotene. Studies on the Interaction of Some Carotenoids with Boron Trifluoride and N-Bromosuccinimide. Provitamin A Activity of a C₄₂-Carotenoid. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/0TZT-6C69. https://resolver.caltech.edu/CaltechETD:etd-05092003-171754

Abstract

NOTE: Text or symbols not renderable in plain ASCII are indicated by [...]. Abstract is included in .pdf document. An extensive study of the stereoisomerization of dehydro-[Beta]-carotene is presented. Two of the cis isomers have been isolated in crystalline form and described. The nature of "isocarotene" has been clarified. Treatment of [Beta]-carotene with boron trifluoride under defined conditions leads chiefly either to its stereoisomerization or chemical conversion. Two of the several conversion products have been crystallized; a third, exhibiting strong fluorescence in ultraviolet light is also described. Three new carotenoids, termed isocryptoxanthin, isocryptoxanthin methyl ether, and dimethoxy-[Beta]-carotene, formed by the addition of water or methanol to dehydro-[Beta]-carotene in the presence of boron trifluoride are described. The structures of the first two compounds have been determined; the location of the substituent groups in the third is, at present, uncertain. Dehydro-[Beta]-carotene, bisdehydro-[Beta]-carotene, and anhydroeschscholtzxanthin have been isolated from the end products of the reaction of [Beta]-carotene with N-bromosuccinimide. Bisdehydro-[Beta]-carotene is a new carotenoid whose probable structure is discussed. The considerable provitamin A potency of 16,16'-homo-[Beta]-carotene is discussed from the standpoint of its novel structural features.

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