Caftaric acid

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Caftaric acid
IUPAC name

(2R,3R)-2-[(E)-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
PubChem 6440397
ChemSpider 4944664 YesY
MeSH caftaric+acid
ChEMBL CHEMBL558557 N
Jmol-3D images {{#if:O=C(O)[C@H](O)[C@@H](OC(=O)\C=C\c1cc(O)c(O)cc1)C(=O)OC1=CC(=C(C=C1/C=C/C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O)O|Image 1
Image 2
Properties
Molecular formula C13H12O9
Molar mass 312.23 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Caftaric acid is a non-flavanoid phenolic compound.

It is found in grape[1] (Vitis vinifera) and impacts the color of white wine. Many believe this molecule is responsible for the yellowish-gold color seen in some whites wines[citation needed]. Aside from wine, it is abundantly present in raisins. It also occurs in Cichorium intybus (common chicory) and is one of the bioactive components of Echinacea purpurea (Eastern purple coneflower).[2]

Caftaric acid and caffeic acid are in a class of chemicals known as cinnamates (hydroxycinnamic acids). Caftaric acid is formed when caffeic acid and tartaric acid undergo esterification. But, during fermentation, caftaric acid is oxidized into its principal components.

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.[2]

In wine

Winemakers measure caftaric acid levels as their primary method to estimate the oxidation 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 grape polyphenol oxidase (PPO), whereas it is degraded in the presence of a crude grape PPO extract and of caftaric acid, forming anthocyanidin-caftaric acid adducts.[3]

See also

References

  1. ↑ C. Y. Lee and A. Jaworski (1987). abstract "Phenolic Compounds in White Grapes Grown in New York". Am. J. Enol. Vitic 38 (4): 277–281. 
  2. ↑ 2.0 2.1 Vanzo, A; Cecotti, R; Vrhovsek, U; Torres, AM; Mattivi, F; Passamonti, S (2007). "The fate of trans-caftaric acid administered into the rat stomach". Journal of agricultural and food chemistry 55 (4): 1604–11. doi:10.1021/jf0626819. PMID 17300159. 
  3. ↑ Sarni-Manchado, Pascale; Cheynier, Véronique; Moutounet, Michel (1997). "Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside". Phytochemistry 45 (7): 1365. doi:10.1016/S0031-9422(97)00190-8. 
Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
Trihydroxycinnamic acids
  • 3,4,6-Trihydroxycinnamic acid
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
  • Chlorogenic acid (3-caffeoylquinic acid)
  • Cryptochlorogenic acid (4-O-caffeoylquinic acid)
  • Neochlorogenic acid (5-O-Caffeoylquinic acid)
  • Cynarine (1,5-dicaffeoylquinic acid)
  • 3,4-dicaffeoylquinic acid
  • 3,5-dicaffeoylquinic acid
esters of
shikimic acid
Glycosides
Tartaric acid esters
Other esters
with caffeic acid
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with coenzyme A
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