Syringic acid

Syringic acid
Chemical structure of syringic acid
Chemical structure of syringic acid
Names
Preferred IUPAC name
4-Hydroxy-3,5-dimethoxybenzoic acid
Other names
Gallic acid 3,5-dimethyl ether
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.716
EC Number
  • 208-486-8
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)
    Key: JMSVCTWVEWCHDZ-UHFFFAOYSA-N
SMILES
  • COC1=CC(=CC(=C1O)OC)C(=O)O
Properties
Chemical formula
 C9H10O5
Molar mass 198.174 g·mol−1
Melting point 206 to 209
Hazards
GHS labelling:[1]
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
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
UV visible spectrum of syringic acid.

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

Natural occurrence

Syringic acid can be found in several plants including Ardisia elliptica and Schumannianthus dichotomus.[1] It is biosynthesized by the shikimic acid pathway in plants.[2]

Synthesis

Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid.[3]

Presence in food

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 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.[6]

Applications

Various studies have found syringic acid to have potentially useful properties such as anti-oxidant, anti-microbial, anti-inflammation, anti-cancer, and anti-diabetic.[2]

Syringic acid can be enzymatically polymerized. 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.[7]

See also

References

  1. ^ 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. Bibcode:2020Plnts...9..102R. doi:10.3390/plants9010102. ISSN 2223-7747. PMC 7020185. PMID 31947649.
  2. ^ a b c Srinivasulu, 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. ISSN 0753-3322. PMID 30243088.
  3. ^ 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.
  4. ^ Pezzuto, John M. (August 2008). "Grapes and Human Health: A Perspective". Journal of Agricultural and Food Chemistry. 56 (16): 6777–6784. Bibcode:2008JAFC...56.6777P. doi:10.1021/jf800898p. ISSN 0021-8561. PMID 18662007.
  5. ^ 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. Bibcode:2008JAFC...56.4631P. doi:10.1021/jf800161u. PMID 18522407.
  6. ^ 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. S2CID 91784893.
  7. ^ 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. ISBN 0-8412-3646-1.
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