Coutaric acid

Coutaric acid is a hydroxycinnamoyltartaric acid found in wine, pomace[1] and grape.[2] It is an ester formed from coumaric acid and tartaric acid.

Coutaric acid
Chemical structure of coutaric acid
Names
Preferred IUPAC name
(2R,3R)-2-Hydroxy-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
Other names
trans-coutaric acid
cis-coutaric acid
trans-p-Coumaroyltartaric acid
cis-p-coumaroyl-(+)-tartaric acid
trans-p-coumaroyl-(+)-tartaric acid
cis-Coumaroyl tartaric acidbr>trans-Coumaroyl tartaric acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3+/t10-,11-/m1/s1 ☒N
    Key: INYJZRKTYXTZHP-NNPIPJJVSA-N ☒N
  • InChI=1/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3+/t10-,11-/m1/s1
    Key: INYJZRKTYXTZHP-NNPIPJJVBX
  • c1cc(ccc1/C=C/C(=O)O[C@H]([C@H](C(=O)O)O)C(=O)O)O
Properties
C13H12O8
Molar mass 296.231 g·mol−1
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


References
  1. Maier, T.; Sanzenbacher, S.; Kammerer, D. R.; Berardini, N.; Conrad, J. R.; Beifuss, U.; Carle, R.; Schieber, A. (2006). "Isolation of hydroxycinnamoyltartaric acids from grape pomace by high-speed counter-current chromatography". Journal of Chromatography A. 1128 (1–2): 61–67. doi:10.1016/j.chroma.2006.06.082. PMID 16860334.
  2. Singleton, V. L.; Zaya, J.; Trousdale, E. K. (1986). "Caftaric and coutaric acids in fruit of Vitis". Phytochemistry. 25 (9): 2127. doi:10.1016/0031-9422(86)80078-4.


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