Caftaric acid

Caftaric acid
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
CAS Number
  • 67879-58-7 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEMBL
  • ChEMBL558557 ☒N
ChemSpider
  • 4944664 checkY
ECHA InfoCard 100.107.739 Edit this at Wikidata
MeSH caftaric+acid
PubChem CID
  • 6440397
UNII
  • WCV7W3174L checkY
CompTox Dashboard (EPA)
  • DTXSID3036866 Edit this at Wikidata
InChI
  • InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1 checkY
    Key: SWGKAHCIOQPKFW-JTNORFRNSA-N checkY
  • InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1
    Key: SWGKAHCIOQPKFW-JTNORFRNBW
  • Key: SWGKAHCIOQPKFW-JTNORFRNSA-N
  • O=C(O)[C@H](O)[C@@H](OC(=O)\C=C\c1cc(O)c(O)cc1)C(=O)O
  • C1=CC(=C(C=C1/C=C/C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O)O
Properties
Chemical formula
 C13H12O9
Molar mass 312.230 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Caftaric acid is a non-flavonoid phenolic compound.

It is found in the juice of grapes[1][2] (Vitis vinifera) and impacts the color of white wine.

It is an esterified phenolic acid, composed of caffeic acid, a hydroxycinnamate produced by plants, and tartaric acid, the principal organic acid found in grape berries. As such, caftaric acid is found in all grape juices and wines.[2] During alcoholic and malolactic 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 wine browning over time, and the straw-gold color that can develop in some white wines after bottling.[2]

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).[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]

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.[4]

See also

References

  1. ^ C. Y. Lee; A. Jaworski (1987). "Phenolic Compounds in White Grapes Grown in New York". Am. J. Enol. Vitic. 38 (4): 277–281. doi:10.5344/ajev.1987.38.4.277. S2CID 102310452.
  2. ^ a b c Waterhouse, Andrew; Sacks, Gavin; Jeffery, David (June 17, 2016). "Chapter 13: Non‐flavonoid Phenolics". Understanding Wine Chemistry. Adelaide: Wiley Books. pp. 112–113. ISBN 978-1-118-73072-0.
  3. ^ a b 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.
  4. ^ Sarni-Manchado, Pascale; Cheynier, Véronique; Moutounet, Michel (August 1997). "Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside". Phytochemistry. 45 (7): 1365–1369. doi:10.1016/S0031-9422(97)00190-8.{{cite journal}}: CS1 maint: date and year (link)
  • v
  • t
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Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
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
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
  • Echinacoside
  • Calceolarioside A, B, C, F
  • Chiritoside A, B, C
  • Cistanoside A, B, C, D, E, F, G, H
  • Conandroside
  • Myconoside
  • Pauoifloside
  • Plantainoside A
  • Plantamajoside
  • Tubuloside B
  • Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)