2,3-Dihydroxybenzoic acid is a natural phenol found in ''

Phyllanthus acidus ''Phyllanthus acidus'', known as the Otaheite gooseberry, Malay gooseberry, Tahitian gooseberry, country gooseberry, star gooseberry, starberry, arbari, West India gooseberry, or simply gooseberry tree, is one of the trees with edible small yell ...

'' and in the aquatic fern ''

Salvinia molesta ''Salvinia molesta'', commonly known as giant salvinia, or as kariba weed after it infested a large portion of Lake Kariba between Zimbabwe and Zambia, is an aquatic fern, native to south-eastern Brazil. It is a free-floating plant that does n ...

''. It is also abundant in the fruits of ''

Flacourtia inermis ''Flacourtia inermis'', known commonly as lovi-lovi, or batoko plum, is a species of flowering plant native to the Philippines and Indonesia, but which has naturalized around the edges of tropical Asia and Africa. Common names in Indonesia inclu ...

''. It is a

dihydroxybenzoic acid Dihydroxybenzoic acids (DHBA) are a type of phenolic acids. There are six main compounds, having all the same molecular formula C7H6O4. Those are: * 2,3-Dihydroxybenzoic acid (2-Pyrocatechuic acid or hypogallic acid) * 2,4-Dihydroxybenzoic acid ...

, a type of organic compound. The colorless solid occurs naturally, being formed via the

shikimate pathway The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine). ...

. It is incorporated into various

siderophore Siderophores (Greek: "iron carrier") are small, high-affinity iron-chelating compounds that are secreted by microorganisms such as bacteria and fungi. They help the organism accumulate iron. Although a widening range of siderophore functions is no ...

s, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a

catechol Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amoun ...

group, which upon deprotonation binds iron centers very strongly, and the

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 ...

group by which the ring attaches to various scaffolds through amide bonds. A famous high affinity siderophore is

enterochelin Enterobactin (also known as enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as ''Escherichia coli'' and ''Salmonella typhimurium''. Enterobactin is the ...

, which contains three dihydroxybenzoyl substituents linked to the depsipeptide of

serine Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − form un ...

. It is a potentially useful

iron-chelating drug Chelation therapy is a medical procedure that involves the administration of chelating agents to remove heavy metals from the body. Chelation therapy has a long history of use in clinical toxicology and remains in use for some very specific med ...

and has

antimicrobial 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 ...

properties. 2,3-Dihydroxybenzoic acid is also a product of human

aspirin Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and as an antithrombotic. Specific inflammatory conditions which aspirin is used to treat inc ...

metabolism.

References

{{DEFAULTSORT:Dihydroxybenzoic acid, 2,3- Dihydroxybenzoic acids Salicylic acids Chelating agents Catechols