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Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.
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
''Schumannianthus dichotomus'', also known as 'cool mat', is a species of flowering plant first described by William Roxburgh, Roxburgh, with its current name after François Gagnepain, Gagnepain. The species belongs to the family Marantaceae and ...
''. It is biosynthesized by the shikimic acid pathway in plants.
Synthesis
Syringic acid can be prepared by selectively hydrolyzing ( demethylating) eudesmic acid with 20%sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
.
Presence in food
Syringic acid can be found in several fruits including olives, dates, spices, pumpkin, grapes, acai palm, honey, red wine, among others. 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.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. Syringic acid can be enzymatically polymerized. Laccase and peroxidase induced the polymerization of syringic acid to give a poly(1,4-phenylene oxide) bearing acarboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
at one end and a phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
ic hydroxyl group at the other.
See also
*Phenolic content in wine
Phenolic compounds— natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilb ...
*Syringol
Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, alth ...
*Syringaldehyde
Syringaldehyde is an organic compound that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. ''Scolytus multistriatus'' uses it as a signal to find a host tree during ovip ...
* Acetosyringone
* Sinapyl alcohol
* Sinapinic acid
* Sinapaldehyde
* Sinapine
* Canolol
References
{{Progestogenics Trihydroxybenzoic acids O-methylated natural phenols Progestogens