Grape reaction product

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Grape reaction product
Chemical structure of grape reaction product
Names
Other names
GRP
GRP1
2-S-Glutathionyl caftaric acid
Identifiers
Jmol 3D model Interactive image
  • Oc1cc(cc(c1O)SCC(NC(=O)CCC(N)C(=O)O)C(=O)NCC(O)=O)\C=C\C(=O)OC(C(O)=O)C(O)C(O)=O
Properties
C23H27N3O15S
Molar mass 617.54 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The grape reaction product (GRP, GRP1 or 2-S-glutathionyl caftaric acid[1]) is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing.[2] It is also found in aged red wines.[3] Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts,[4] especially in white wine production. The product can be recreated in model solutions.[5][6]

It is possible to determine its concentration in wine by mass spectrometry.[7]

S-Glutathionyl caftaric acid is itself oxidizable.[8] It is not a substrate for grape polyphenol oxidase, but laccase from Botrytis cinerea can use it to form GRP2.[9]

Related molecules

Other related molecules are trans-caffeoyltartrate derivatives like GRP o-quinone[10] and 2,5-di-S-glutathionyl cafteoyl tartrate (GRP2)[11] or adducts with anthocyanidins.[12]

File:GRP UV visible spectrum.png
GRP UV visible spectrum

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Caftaric acid in grapes and conversion to a reaction product during processing. V.L. Singleton, J. Zaya, E. Trousdale and M. Salgues, Vitis, 1984, pages 113-120 (article)
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Straightforward Method To Quantify GSH, GSSG, GRP, and Hydroxycinnamic Acids in Wines by UPLC-MRM-MS. Anna Vallverdú-Queralt, Arnaud Verbaere, Emmanuelle Meudec, Veronique Cheynier and Nicolas Sommerer, J. Agric. Food Chem. 2015, 63, 142−149, doi:10.1021/jf504383g
  8. ↑ 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, 1985, volume 36, number 1, pages 50-56 'abstract)
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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