Grape reaction product

Grape reaction product
Other names

GRP
GRP1
2-S-glutathionyl caftaric acid
Identifiers
Jmol-3D images Image 1
Properties
Molecular formula C23H27N3O15S
Molar mass 617.53 g/mol
Exact mass 617.11628811 u
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The grape reaction product (GRP, GRP1 or 2-S-glutathionyl caftaric acid[1]) is a phenolic compound found in aged red wines.[2] Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts.[3] The product can be recreated in model solutions.[4][5] Other related molecules are trans-caffeoyltartrate derivatives like GRP o-quinone[6] and 2,5-di-S-glutathionyl cafteoyl tartrate (GRP2)[7] or adducts with anthocyanidins.[8]

See also

References

  1. ^ Characterization of 2-S-glutathionyl caftaric acid and its hydrolysis in relation to grape wines. Veronique F. Cheynier, Eugene K. Trousdale, Vernon L. Singleton, Michel J. Salgues and Renee Wylde, J. Agric. Food Chem., 1986, 34 (2), pp 217–221, doi:10.1021/jf00068a016
  2. ^ Effect of Principal Polyphenolic Components in Relation to Antioxidant Characteristics of Aged Red Wines. Anis Arnous, Dimitris P. Makris and Panagiotis Kefalas, J. Agric. Food Chem. 2001, 49, pp. 5736−5742, doi:10.1021/jf010827s
  3. ^ Caftaric Acid Disappearance and Conversion to Products of Enzymic Oxidation in Grape Must and Wine. V.L. Singleton, M. Salgues, J. Zaya and E. Trousdale, Am. J. Enol. Vitic., Vol. 36, No. 1, 1985
  4. ^ Oxidation of Grape Juice Phenolic Compounds in Model Solutions. V. Cheynier, C. Owe and J. Rigaud, Journal of Food Science, Volume 53, Issue 6, pages 1729–1732, November 1988, doi:10.1111/j.1365-2621.1988.tb07828.x
  5. ^ Oxidation of grape procyanidins in model solutions containing trans-caffeoyltartaric acid and polyphenol oxidase. Veronique Cheynier and Jorge M. Ricardo da Silva, J. Agric. Food Chem., 1991, 39 (6), pp 1047–1049, doi:10.1021/jf00006a008
  6. ^ Must browning in relation to the behavior of phenolic compounds during oxidation. Cheynier V., Rigaud J., Souquet J.-M., Duprat F. and Moutounet M., American journal of enology and viticulture, 1990, vol. 41, no4, pp. 346-349, INIST:5402970
  7. ^ Oxidation kinetics of trans-caffeoyltartrate and its glutathione derivatives in grape musts. Véronique Cheynier, Jacques Rigaud and Michel Moutounet, Phytochemistry, Volume 29, Issue 6, 1990, pp. 1751-1753, doi:10.1016/0031-9422(90)85008-4
  8. ^ New Phenolic Grape Skin Products from Vitis vinifera cv. Pinot Noir. Petros Kneknopoulos, George K. Skouroumounis, Yoji Hayasaka and Dennis K. Taylor, J. Agric. Food Chem. 2011, 59, pp. 1005–1011, doi:10.1021/jf103682x
Hydroxycinnamic acids
Glycosides
Tartaric acid esters
Others
Grape reaction product