Jump to content

Fertaric acid

From Wikipedia, the free encyclopedia
Fertaric acid
Chemical structure of fertaric acid
(2S,3S)-stereoisomer
Names
IUPAC name
2-Hydroxy-3-{[(2E)-3-(4-hydroxy-3methoxyphenyl)prop-2-enoyl]oxy}butandioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+
    Key: XIWXUSFCUBAMFH-HWKANZROSA-N
  • 2S,3S,trans: InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+/t11-,12-/m0/s1
    Key: XIWXUSFCUBAMFH-SCBUBVSKSA-N
  • Oc1ccc(cc1OC)/C=C/C(=O)OC(C(=O)O)C(O)C(=O)O
  • 2S,3S,trans: COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]([C@@H](C(=O)O)O)C(=O)O)O
Properties
C14H14O9
Molar mass 326.257 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 ?)

Fertaric acid is a hydroxycinnamic acid found in wine and grapes.[1] It is an ester formed from ferulic acid bound to tartaric acid.

It is a metabolite of caftaric acid after caftaric acid has been fed to rats. Fertaric acid is then found in plasma, kidney, and urine.[2]

References

[edit]
  1. ^ Branka Mozetič; Irma Tomažič; Andreja Škvarč; Polonca Trebše (2006). "Determination of Polyphenols in White grape Berries cv. Rebula" (PDF). Acta Chim. Slov. 53: 58–64. Archived from the original (PDF) on 2011-08-07.
  2. ^ 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.