Syringic acid
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| Names | |
|---|---|
| Preferred IUPAC name
4-Hydroxy-3,5-dimethoxybenzoic acid | |
| 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 |
| KEGG | |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C9H10O5 | |
| Molar mass | 198.174g·mol−1 |
| Melting point | 206 to 209 |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Syringic acidis a naturally occurringphenolic compoundanddimethoxybenzenethat is commonly found as a plant metabolite.
Natural occurrence
[edit]Syringic acid can be found in several plants includingArdisia ellipticaandSchumannianthus dichotomus.[1]It is biosynthesized by theshikimic acid pathwayin plants.[2]
Synthesis
[edit]Syringic acid can be prepared by selectivelyhydrolyzing(demethylating)eudesmic acidwith 20%sulfuric acid.[3]
Presence in food
[edit]Syringic acid can be found in several fruits including olives, dates, spices, pumpkin, grapes,[4]acai palm,[5]honey, red wine, among others.[2]Its presence in the ancient Egyptian drinkshedehcould confirm it was made out of grape, as syringic acid is released by the breakdown of the compoundmalvidin,also found inred wine.It is also found invinegar.[6]
Applications
[edit]Various studies have found syringic acid to have potentially useful properties such asanti-oxidant,anti-microbial,anti-inflammation,anti-cancer,andanti-diabetic.[2]
Syringic acid can beenzymaticallypolymerized.Laccaseandperoxidaseinduced the polymerization of syringic acid to give apoly(1,4-phenylene oxide)bearing acarboxylic acidat one end and aphenolichydroxyl group at the other.[7]
See also
[edit]References
[edit]- ^Rob, Md. Mahfuzur; Hossen, Kawsar; Iwasaki, Arihiro; Suenaga, Kiyotake; Kato-Noguchi, Hisashi (2020-01-14)."Phytotoxic Activity and Identification of Phytotoxic Substances from Schumannianthus dichotomus".Plants.9(1): 102.doi:10.3390/plants9010102.ISSN2223-7747.PMC7020185.PMID31947649.
- ^abcSrinivasulu, Cheemanapalli; Ramgopal, Mopuri; Ramanjaneyulu, Golla; Anuradha, C.M.; Suresh Kumar, Chitta (December 2018)."Syringic acid (SA) ‒ A Review of Its Occurrence, Biosynthesis, Pharmacological and Industrial Importance".Biomedicine & Pharmacotherapy.108:547–557.doi:10.1016/j.biopha.2018.09.069.ISSN0753-3322.PMID30243088.
- ^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.Retrieved2 November2013.
- ^Pezzuto, John M. (August 2008). "Grapes and Human Health: A Perspective".Journal of Agricultural and Food Chemistry.56(16): 6777–6784.doi:10.1021/jf800898p.ISSN0021-8561.PMID18662007.
- ^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.PMID18522407.
- ^Gálvez, Miguel Carrero; Barroso, Carmelo García; Pérez-Bustamante, Juan Antonio (1994). "Analysis of polyphenolic compounds of different vinegar samples".Zeitschrift für Lebensmittel-Untersuchung und -Forschung.199:29–31.doi:10.1007/BF01192948.S2CID91784893.
- ^Uyama, Hiroshi; Ikeda, Ryohei; Yaguchi, Shigeru; Kobayashi, Shiro (2001). "Enzymatic Polymerization of Natural Phenol Derivatives and Enzymatic Synthesis of Polyesters from Vinyl Esters".Polymers from Renewable Resources.ACS Symposium Series. Vol. 764. p. 113.doi:10.1021/bk-2000-0764.ch009.ISBN0-8412-3646-1.