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''.
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 ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular fo ...
.
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
Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to et ...
.
Applications
Various studies have found syringic acid to exhibit useful pharmaceutical properties such as
anti-oxidant,
anti-microbial
An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...
,
anti-inflammation,
anti-cancer
Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal bl ...
, and
anti-diabetic.
Syringic acid can be
enzymatically polymerised.
Laccase
Laccases () are multicopper oxidases found in plants, fungi, and bacteria. Laccases oxidize a variety of phenolic substrates, performing one-electron oxidations, leading to crosslinking. For example, laccases play a role in the formation of li ...
and
peroxidase
Peroxidases or peroxide reductases ( EC numberbr>1.11.1.x are a large group of enzymes which play a role in various biological processes. They are named after the fact that they commonly break up peroxides.
Functionality
Peroxidases typically c ...
induced the polymerization of syringic acid to give a
poly(1,4-phenylene oxide) bearing a
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
at one end and a
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it re ...
ic hydroxyl group at the other.
See also
*
Phenolic content in wine
The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ...
*
Syringol
*
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
Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which ar ...
*
Sinapinic acid
Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mass ...
*
Sinapaldehyde
Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a ...
*
Sinapine
*
Canolol
References
{{Progestogenics
Trihydroxybenzoic acids
O-methylated natural phenols
Progestogens