Phenolation of ±catechin with mineral acids. II. Identification of new reaction productsAuthor(s): Weiling Peng; Anthony H. Conner; Richard W. Hemingway
Source: Journal of Wood Chemistry and Technology. 17(4):341-360.
Publication Series: Miscellaneous Publication
PDF: View PDF (364 B)
DescriptionTo investigate the reactions that occur in the flavanoid unit during the liquefaction of tannin in phenol, the phenolysis of ±catechin was studied using either H2SO4, HCl, or BF3 2H2O as acid catalyst. In addition to 2-[3-(3,4-dihydroxyphenyl)-2-hydroxy-3-(4-hydroxyphenyl)propyl]-1,3,5-benzenetriol (1) and 2-[(3,4-dihydroxyphenyl)(4-hydroxyphenyl)methyl]-2,3-dihydro-4,6-benzofurandiol (3) that have been described previously, eight additional reaction products were isolated, four of which were compounds that have not been described previously. The novel compounds described here are: 2-[3-(3,4-dihydroxyphenyl)-2-hydroxy-3(2-hydroxyphenyl)propyl]-1,3,5-benzenetriol (2), 2-[(3,4-dihydroxyphenyl)(2-hydroxyphenyl)methyl]-2,3-dihydro-4,6-benzofurandiol (4), 2-[(3,4-dihydroxyphenyl)(4-hydroxyphenyl)methyl]-2,3-dihydro-7-(4-hydroxyphenyl)methyl-4,6-benzofurandiol (5), and 2-(1,3,5-trihydroxyphenyl)methyl-3-(3,4-dihydroxyphenyl)-6-[(3,4-dihydroxyphenyl)- -(4-hydroxyphenyl)methyl]-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b`]-difuran-4-ol (6).
The structures of these and other previously described products are consistent with opening of the pyran ring of catechin and reaction at C-2 by either the para or the ortho position of phenol. Additional products resulting from reaction between pyran ring cleavage products and catechin, and from reaction of cleavage products were found. Similar reactions would be expected to take place during the phenolysis of condensed tannins.
- You may send email to email@example.com to request a hard copy of this publication.
- (Please specify exactly which publication you are requesting and your mailing address.)
- We recommend that you also print this page and attach it to the printout of the article, to retain the full citation information.
- This article was written and prepared by U.S. Government employees on official time, and is therefore in the public domain.
CitationPeng, Weiling; Conner, Anthony H.; Hemingway, Richard W. 1997. Phenolation of ±catechin with mineral acids. II. Identification of new reaction products. Journal of Wood Chemistry and Technology. 17(4):341-360.
- Condensed tannins: Base-catalysed reactions of polymeric procyanidins with toluene-α-thiol, liability of the interflavanoid bond and pyran ring
- Condensed tannins. Base-catalysed reactions of polymeric procyanidins with phloroglucinol: Intramolecular rearrangements
- Condensed tannins: The formation of a diarylpropanol-catechinic acid dimer from base-catalyzed reactions of (+)-catechin
XML: View XML