 | |
| Names | |
|---|---|
| Preferred IUPAC name (2R,3R)-2-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid | |
| Other names Monocaffeyltartaric acid Butanedioic acid, 2-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-3-hydroxy-, (R-(R*,R*-(E)))- trans-Caftaric acid cis-Caftaric acid trans-Caffeoyl tartaric acid cis-Caffeoyl tartaric acid | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.107.739 |
| MeSH | caftaric+acid |
| UNII | |
| |
| |
| Properties | |
| C13H12O9 | |
| Molar mass | 312.230 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Caftaric acid is a non-flavonoid phenolic compound.
It is found in the juice of grapes[1][2] (Vitis vinifera) and impacts the color ofwhite wine.
It is an esterified phenolic acid, composed ofcaffeic acid, ahydroxycinnamate produced by plants, andtartaric acid, the principal organic acid found in grape berries. As such, caftaric acid is found in all grape juices and wines.[2] Duringalcoholic andmalolactic fermentation, the ester can be enzymatically hydrolysed, releasing the two constituents. Caffeic acid is susceptible to chemical oxidation, and subsequent redox reactions involving caffeic acid can contribute to winebrowning over time, and the straw-gold color that can develop in some white wines after bottling.[2]
Aside from wine, it is abundantly present inraisins. It also occurs inCichorium intybus (commonchicory) and is one of the bioactive components ofEchinacea purpurea (Eastern purple coneflower).[3]
Caftaric acid has a good bioavailability when fed in rats. Intact trans-caftaric acid was detected in rat plasma along with its O-methylated derivative trans-fertaric acid.[3]
Winemakers measure caftaric acid levels as their primary method to estimate theoxidation levels that a wine has undergone. For example,press wines, which undergo a high degree of oxidation[citation needed], will have little to no caftaric acid.
Grape reaction product (2-S glutathionyl caftaric acid) is an oxidation compound produced from caftaric acid and found in wine.Malvidin 3-glucoside alone is not oxidized in the presence of grapepolyphenol oxidase (PPO), whereas it is degraded in the presence of a crude grape PPO extract and of caftaric acid, forminganthocyanidin-caftaric acid adducts.[4]
