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Catechin and hydroxybenzhydrols as models for the environmental photochemistry of tannins and lignins

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Abstract

The photochemistry of several model plant-derived compounds has been studied in aqueous solution. In particular, the reactions of catechin as a model tannin and methoxy-substituted hydroxybenzhydrols as model lignin functionalities were investigated. Tannins and lignins constitute a significant portion of the humic substances in aquatic systems, which are themselves the main component of dissolved organic matter thought to be responsible for the absorption and attenuation of light in these environments. Catechin (1) was found to undergo a reversible photoisomerization reaction to give epicatechin (2). Such a reaction is an explicit example of a photon absorbing process that enables catechin (1) and its derivatives to act as natural sunscreens by attenuating light energy through non-destructive reactions. The methoxy-substituted hydroxybenzhydrols were found to undergo photosolvolysis reactions via efficient generation of quinone methide intermediates. The intermediate quinone methides were observed to be longer lived, and thus more stable, than previously studied hydroxybenzhydrol derivatives. The meta-hydroxybenzhydrol isomer (5) was found to undergo additional chemistry leading to the production of a ring-closed fluorene from the quinone methide intermediate.

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Authors and Affiliations

  1. Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, British Columbia, Canada, V8W 3V6

    Kaya Forest & Peter Wan

  2. Pacific Forestry Centre, Natural Resources Canada, 506 West Burnside Road, Victoria, British Columbia, Canada, V8Z 1M5

    Caroline M. Preston

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  1. Kaya Forest
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  2. Peter Wan
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  3. Caroline M. Preston
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Correspondence to Peter Wan.

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Forest, K., Wan, P. & Preston, C.M. Catechin and hydroxybenzhydrols as models for the environmental photochemistry of tannins and lignins. Photochem Photobiol Sci 3, 463–472 (2004). https://doi.org/10.1039/b402241f

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