Syringic acid
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| Names | |
|---|---|
| IUPAC name
4-Hydroxy-3,5-dimethoxybenzoic acid
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| Other names
Gallic acid 3,5-dimethyl ether
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ECHA InfoCard | 100.007.716 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C9H10O5 | |
| Molar mass | 198.174 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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Syringic acid is a naturally occurring O-methylated trihydroxybenzoic acid, a type of chemical compound.
Natural occurrence
Syringic acid can be found in Ardisia elliptica.
Synthesis
Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid.[1]
Presence in food
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
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
References
- ^ 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.
- ^ "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. Jun 2008. doi:10.1021/jf800161u. PMID 18522407.
{{cite journal}}: Unknown parameter|authors=ignored (help) - ^ 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
- ^ Uyama, Hiroshi; Ikeda, Ryohei; Yaguchi, Shigeru; Kobayashi, Shiro (2001). "Polymers from Renewable Resources". ACS Symposium Series. 764: 113. doi:10.1021/bk-2000-0764.ch009. ISBN 0-8412-3646-1.
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