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Reduction of trans-cinnamaldehyde by hydrogenation over Raney nickel mediated by derivatives of Beta-cyclodextrin.

Ravichandran, R. and Divakar, S. (1996) Reduction of trans-cinnamaldehyde by hydrogenation over Raney nickel mediated by derivatives of Beta-cyclodextrin. Indian Journal of Chemistry, 35B (11). pp. 1167-1173.

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Abstract

The extent and rates of reduction of both olefinic double bond and the aldehyde functions have been found to be altered in the reduction of cinnamaldehyde over Raney nickel. The formation of 3-phenylpropanol is found to be faster in the presence of BCD than the control and is slower in the case of DMBCD and BCD-polymer mediated reactions than the control. The reactions mediated by BCD, BCD-polymer and DMBCD have been found to maintain a certain proportion of equilibrium concentration of 3-phenylpropanal, i.e. 18-29%, 34-37% and 45-48% respectively for sometime after which complete conversion to 3-phenylpropanol is effected. The reduction of double bond is found to be faster than that of the aldehydic function in all the four cases. UV, 1H and 13C NMR spectroscopic studies of both BCD and DMBCD complexes indicate more than one mode of disposition for cinnamaldehyde inside the cyclodextrin cavity. Although the phenyl ring is found to be embedded inside the cavity in both the cases, α, ß-unsaturated aldehydic function is found to be partially exposed. In the case of DMBCD a 1:2 (DMBCD: cinnamaldehyde) complex is detected and in the case of BCD, a 1:1 complex is detected with binding constant values of 17370 ± 1000 M-1 and 27390 ±2600 M-1, respectively.

Item Type: Article
Uncontrolled Keywords: cinnamaldehyde, ß-cyclodextrin
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 24 Organic Chemistry
Divisions: Food Microbiology
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 19 Apr 2012 04:00
Last Modified: 19 Apr 2012 04:00
URI: http://ir.cftri.com/id/eprint/2887

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