Southern Research Station

Title: Condensed tannins: Reactions of model compounds with furfuryl alcohol and furfuraldehyde

Author: Foo, L.; Hemingway, Richard W.

Date: 1985

Source: Journal of Wood Chemistry and Technology 5(1):135-158

Description: Reaction products of phloroglucinol or catechin with furfuryl alcohol and furfuraldehyde were studied. In reactions of furfuryl alcohol with phloroglucinol, only 2-furyl-(1¹, 3¹, 5¹-trihydroxyphenyl) methane was obtained as product, and 53% of the phloroglucinol was recovered. Reactions of furfuryl alcohol with catechin gave 2-furyl-(8-catechinyl) methane and 2-furyl-(6-catechinyl) methane in 4.0% and 1.5% yields, respectively, while 62% of the catechin was unreacted. Polymeric furans with few catechin moieties made up the oligomeric products (38% of catechin). Reaction of phloroglucinol with furfuraldehyde gave 2-furyl-di(1¹, 3¹, 5¹-trihydroxyphenyl) methane, an ustable product that readily polymerized during isolation. The solid state ¹³C-NMR spectrum of the higher polymers suggested one phloroglucinol moiety per furan unit, but lower oligomers contained more furan-furan condensation products. Reactions of catechin with furfuraldehyde gave 2-furyl-di(8-catechinyl)-(8-catechinyl) methane in low yield, with 65% of the catechin unreacted.

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Citation

Foo, L.; Hemingway, Richard W.  1985.  Condensed tannins: Reactions of model compounds with furfuryl alcohol and furfuraldehyde.   Journal of Wood Chemistry and Technology 5(1):135-158