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.
Item Type: | Thesis (Dissertation (Ph.D.)) |
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Subject Keywords: | (Chemistry and Physics) |
Degree Grantor: | California Institute of Technology |
Division: | Chemistry and Chemical Engineering |
Major Option: | Chemistry |
Minor Option: | Physics |
Thesis Availability: | Public (worldwide access) |
Research Advisor(s): |
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Thesis Committee: |
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Defense Date: | 1 January 1953 |
Additional Information: | Title varies in the 1953 Caltech Commencement program: I. The Stereochemistry of Dehydro-Beta-Carotene. II. Studies on the Interaction of Some Carotenoids with Boron Trifluoride and N-Bromosuccinimide. Ill. Provitamin A Activity of a C₄₂-Carotenoid. |
Record Number: | CaltechETD:etd-05092003-171754 |
Persistent URL: | https://resolver.caltech.edu/CaltechETD:etd-05092003-171754 |
DOI: | 10.7907/0TZT-6C69 |
Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. |
ID Code: | 1700 |
Collection: | CaltechTHESIS |
Deposited By: | Imported from ETD-db |
Deposited On: | 14 May 2003 |
Last Modified: | 26 May 2023 19:06 |
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