Syringic acid

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Syringic acid
Chemical structure of syringic acid
Identifiers
CAS number 530-57-4 YesY
PubChem 10742
ChEMBL CHEMBL1414 N
Jmol-3D images Image 1
Properties
Molecular formula C9H10O5
Molar mass 198.17 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
UV visible spectrum of syringic acid.

Syringic acid is a naturally occurring O-methylated trihydroxybenzoic acid, a type of chemical compound.

Natural occurrences[edit]

Syringic acid can be found in Ardisia elliptica.

Synthesis[edit]

Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid.[1]

Presence in food[edit]

Syringic acid can be found in the açaí palm (Euterpe oleracea) and its oil (1,073 ± 62 mg/kg).[2]

It is also present in wine. Its presence in the ancient Egyptian drink shedeh could confirm it was made out of grape, as syringic acid is released by the breakdown of the compound malvidin, also found in red wine. It is also found in vinegar.[3]

Applications[edit]

Syringic acid can be enzymatically polymerised. Laccase and peroxidase induced the polymerization of syringic acid to give a poly(1,4-phenylene oxide) bearing a carboxylic acid at one end and a phenolic hydroxyl group at the other.[4]

See also[edit]

References[edit]

  1. ^ Bogert, Marston; Ehrlich, Jacob (Mar 1919). "The synthesis of certain pyrogallol ethers, including a new acetophenetide derived from the ethyl ether of syringic acid". Journal of the American Chemical Society 41 (5): 798–810. doi:10.1021/ja02226a013. Retrieved 2 November 2013. 
  2. ^ Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)". J Agric Food Chem 56 (12): 4631–4636. doi:10.1021/jf800161u. PMID 18522407. 
  3. ^ Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pages 29–31, doi:10.1007/BF01192948
  4. ^ Uyama, Hiroshi; Ikeda, Ryohei; Yaguchi, Shigeru; Kobayashi, Shiro (2001). "Polymers from Renewable Resources". ACS Symposium Series 764. p. 113. doi:10.1021/bk-2000-0764.ch009. ISBN 0-8412-3646-1.  |chapter= ignored (help)