2,3-Dihydroxybenzoic acid

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2,3-Dihydroxybenzoic acid
2,3-Dihydroxybenzoesaure.svg
Names
Preferred IUPAC name
2,3-Dihydroxybenzoic acid
Other names
Hypogallic acid; 2-Pyrocatechuic acid; o-Pyrocatechuic acid
Identifiers
3D model (JSmol)
Abbreviations2,3-DHBA; 2,3-DHB
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.582 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) Yes check.svgY
    Key: GLDQAMYCGOIJDV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
    Key: GLDQAMYCGOIJDV-UHFFFAOYAE
  • O=C(O)c1cccc(O)c1O
  • c1cc(c(c(c1)O)O)C(=O)O
Properties
C7H6O4
Molar mass 154.121 g·mol−1
AppearanceColorless solid
Density 1.542 g/cm3 (20 °C) [1]
Melting point 205 °C (401 °F; 478 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

2,3-Dihydroxybenzoic acid is a natural phenol found in Phyllanthus acidus [2] and in the aquatic fern Salvinia molesta . [3] It is also abundant in the fruits of Flacourtia inermis . It is a dihydroxybenzoic acid, a type of organic compound.

The colorless solid occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds through amide bonds. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsipeptide of serine. [4] [5]

It is a potentially useful iron-chelating drug [6] and has antimicrobial properties. [7] [8] [9]

2,3-Dihydroxybenzoic acid is also a product of human aspirin metabolism. [10]

Related Research Articles

<i>Salvinia molesta</i> Species of aquatic plant

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 not attach to the soil, but instead remains buoyant on the surface of a body of water. The fronds are 0.5–4 cm long and broad, with a bristly surface caused by the hair-like strands that join at the end to form eggbeater shapes. They are used to provide a waterproof covering. These fronds are produced in pairs also with a third modified root-like frond that hangs in the water. It has been accidentally introduced or escaped to countless lakes throughout the United States, including Caddo Lake in Texas, where the invasive species has done extensive damage, killing off other life.

<span class="mw-page-title-main">Siderophore</span> Iron compounds secreted by microorganisms

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 now being appreciated, siderophores are among the strongest (highest affinity) Fe3+ binding agents known. Phytosiderophores are siderophores produced by plants.

<i>Phyllanthus acidus</i> Berry and plant

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 yellow berries fruit in the family Phyllanthaceae. Despite its name, the plant does not resemble the gooseberry, except for the acidity of its fruits. It tastes sour and tart.

<span class="mw-page-title-main">Methyl benzoate</span> Chemical compound

Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5CO2CH3. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents. Methyl benzoate has a pleasant smell, strongly reminiscent of the fruit of the feijoa tree, and it is used in perfumery. It also finds use as a solvent and as a pesticide used to attract insects such as orchid bees.

<span class="mw-page-title-main">Hydroxamic acid</span> Organic compounds of the form –C(=O)N(OH)–

In organic chemistry, hydroxamic acids are a class of organic compounds bearing the functional group R−C(=O)−N(OH)−R', with R and R' as organic residues. They are amides wherein the nitrogen center has a hydroxyl substituent. They are often used as metal chelators.

<span class="mw-page-title-main">Enterobactin</span> Chemical compound

Enterobactin 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.

In enzymology, a 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase (EC 1.3.1.28) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">5-Hydroxyeicosatetraenoic acid</span> Chemical compound

5-Hydroxyeicosatetraenoic acid (5-HETE, 5(S)-HETE, or 5S-HETE) is an eicosanoid, i.e. a metabolite of arachidonic acid. It is produced by diverse cell types in humans and other animal species. These cells may then metabolize the formed 5(S)-HETE to 5-oxo-eicosatetraenoic acid (5-oxo-ETE), 5(S),15(S)-dihydroxyeicosatetraenoic acid (5(S),15(S)-diHETE), or 5-oxo-15-hydroxyeicosatetraenoic acid (5-oxo-15(S)-HETE).

<span class="mw-page-title-main">Ferrichrome</span> Chemical compound

Ferrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.

<span class="mw-page-title-main">Rhodotorulic acid</span> Chemical compound

Rhodotorulic acid is the smallest of the 2,5-diketopiperazine family of hydroxamate siderophores which are high-affinity chelating agents for ferric iron, produced by bacterial and fungal phytopathogens for scavenging iron from the environment. It is a tetradentate ligand, meaning it binds one iron atom in four locations (two hydroxamate and two lactam moieties), and forms Fe2(siderophore)3 complexes to fulfill an octahedral coordination for iron.

Ferroverdin refers to three different coordination compounds that were first isolated in 1955 by Chain, Tonolo, and Carilli. It consists of three p-vinylphenyl-3-nitroso-4-hydroxybenzoate ligands complexed with a ferrous ion. Ferroverdin is a green pigment produced in the mycelium of species of Streptomyces. It is claimed to be the “first stable ferrous compound to be found in nature.” There are three types of ferroverdin: A, B, and C. In ferroverdin A, both R groups are hydrogens. In ferroverdin B, R1 is a hydroxyl group (OH) and R2 is a hydrogen (according to a diagram in the paper, the R-groups are on the vinyl group, on the carbon opposite the phenyl; they are respectively trans and cis relative to the phenyl group). In ferroverdin C, R1 is a hydrogen while R2 is a carboxyl group (COOH). Ferroverdin is immune to chelating and oxidizing agents due to the strong interaction between the ligands and ferrous ion. However, it can be broken down by reductive processes.1 The presence of ferroverdin peaks when there are four to eight μg/mL of Fe2+ in the media usually in the form of a salt.

<span class="mw-page-title-main">2,6-Pyridinedicarbothioic acid</span> Chemical compound

2,6-Pyridinedicarbothioic acid (PDTC) is an organosulfur compound that is produced by some bacteria. It functions as a siderophore, a small chelating agent with a high affinity for iron. Siderophores are deployed as ion scavengers for microbes. Siderophores solubilize compounds by forming strong complexes. PDTC is secreted by the soil bacteria Pseudomonas stutzeri and Pseudomonas putida.

<span class="mw-page-title-main">Paeoniflorin</span> Chemical compound

Paeoniflorin is a chemical compound which is one of the major constituents of an herbal medicine derived from Paeonia lactiflora. It can also be isolated from the fresh water fern Salvinia molesta.

<span class="mw-page-title-main">Ascorbate ferrireductase (transmembrane)</span> Class of enzymes

Ascorbate ferrireductase (transmembrane) (EC 1.16.5.1, cytochrome b561) is an enzyme with systematic name Fe(III):ascorbate oxidorectuctase (electron-translocating). This enzyme catalyses the following chemical reaction

<i>Flacourtia inermis</i> Species of flowering plant

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 include Tome-Tome, Lovi-lovi, and lobi-lobi.

N2-citryl-N6-acetyl-N6-hydroxylysine synthase (EC 6.3.2.38, N(alpha)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine synthase, iucA (gene)) is an enzyme with systematic name citrate:N6-acetyl-N6-hydroxy-L-lysine ligase (ADP-forming). This enzyme catalyses the following chemical reaction

Siderocalin(Scn), lipocalin-2, NGAL, 24p3 is a mammalian lipocalin-type protein that can prevent iron acquisition by pathogenic bacteria by binding siderophores, which are iron-binding chelators made by microorganisms. Iron serves as a key nutrient in host-pathogen interactions, and pathogens can acquire iron from the host organism via synthesis and release siderophores such as enterobactin. Siderocalin is a part of the mammalian defence mechanism and acts as an antibacterial agent. Crystallographic studies of Scn demonstrated that it includes a calyx, a ligand-binding domain that is lined with polar cationic groups. Central to the siderophore/siderocalin recognition mechanism are hybrid electrostatic/cation-pi interactions. To evade the host defences, pathogens evolved to produce structurally varied siderophores that would not be recognized by siderocalin, allowing the bacteria to acquire iron.

<span class="mw-page-title-main">Rebecca Abergel</span> French inorganic chemist

Rebecca Abergel is a French inorganic chemist who specializes in the coordination chemistry between lanthanide and actinide complexes. Alongside the effects of heavy element exposure and contamination on different biological systems. Abergel is currently a faculty scientist and heavy element chemistry group leader at the chemical sciences division of Lawrence Berkeley National Laboratory in Berkeley, California. She is also assistant professor of nuclear engineering at University of California, Berkeley.

<span class="mw-page-title-main">Vibriobactin</span> Chemical compound

Vibriobactin is a catechol siderophore that helps the microbial system to acquire iron. It was first isolated from Vibrio cholerae.

<span class="mw-page-title-main">Mirubactin</span> Chemical compound

Mirubactin is a siderophore produced by the bacterium Actinosynnema mirum.A.mirum was first isolated from the Raritan River in New Jersey in 1976, and its full genome sequence was published in 2009. In 2012, mirubactin was isolated and characterized, and the biosynthesis was connected with the gene cluster Amir_2714-Amir_2728, since renamed mrbA-mrbO.

References

  1. 1 2 Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.190. ISBN   9781498754293.
  2. Sousa M, Ousingsawat J, Seitz R, et al. (January 2007). "An extract from the medicinal plant Phyllanthus acidus and its isolated compounds induce airway chloride secretion: A potential treatment for cystic fibrosis". Mol. Pharmacol. 71 (1): 366–76. doi:10.1124/mol.106.025262. PMID   17065237. S2CID   5793585.
  3. Choudhary, M. I.; Naheed, N.; Abbaskhan, A.; Musharraf, S. G.; Siddiqui, H.; Atta-Ur-Rahman (2008). "Phenolic and other constituents of fresh water fern Salvinia molesta". Phytochemistry. 69 (4): 1018–1023. doi:10.1016/j.phytochem.2007.10.028. PMID   18177906.
  4. O'Brien, I. G.; Cox, G. B.; Gibson, F. (1970). "Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli". Biochimica et Biophysica Acta (BBA) - General Subjects . 201 (3): 453–60. doi:10.1016/0304-4165(70)90165-0. PMID   4908639.
  5. Young, I. G.; Gibson, F. (1969). "Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in Aerobacter aerogenes and Escherichia coli". Biochimica et Biophysica Acta (BBA) - General Subjects. 177 (3): 401–11. doi:10.1016/0304-4165(69)90302-X. PMID   4306838.
  6. Graziano, J. H.; Grady, R. W.; Cerami, A. (1974). "The identification of 2,3-dihroxybenzoic acid as a potentially useful iron-chelating drug". Journal of Pharmacology and Experimental Therapeutics. 190 (3): 570–575. PMID   4416298.
  7. George, Shibumon; PJ, Benny; Kuriakose, Sunny; George, Cincy (2011). "Antibiotic activity of 2, 3-dihydroxybenzoic acid isolated from Flacourtia inermis fruit against multidrug resistant bacteria" (PDF). Asian Journal of Pharmaceutical and Clinical Research. 4 (1).
  8. PJ, Benny; Shibumon, George; Sunny, Kuriakose; Cincy, George (2010). "2, 3-Dihydroxybenzoic Acid: An Effective Antifungal Agent Isolated from Flacourtia inermis Fruit". International Journal of Pharmaceutical and Clinical Research. 2 (3): 101–105.
  9. George, Shibumon; PJ, Benny; Kuriakose, Sunny; George, Cincy; Sarala, Gopalakrishnan (2011). "Antiprotozoal activity of 2, 3-dihydroxybenzoic acid isolated from the fruit extracts of Flacourtia inermis Roxb". Medicinal Plants - International Journal of Phytomedicines and Related Industries. 3 (3): 237–241. doi:10.5958/j.0975-4261.3.3.038.
  10. Grootveld, M.; Halliwell, B. (1988). "2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism". Biochemical Pharmacology. 37 (2): 271–280. doi:10.1016/0006-2952(88)90729-0. PMID   3342084.