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2,3-Dihydroxybenzoic acid

From Wikipedia, the free encyclopedia
2,3-Dihydroxybenzoic acid
Names
Preferred IUPAC name
2,3-Dihydroxybenzoic acid
Other names
  • Hypogallic acid
  • 2-Pyrocatechuic acid
  • o-Pyrocatechuic acid
Identifiers
3D model (JSmol)
Abbreviations
  • 2,3-DHBA
  • 2,3-DHB
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.005.582Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) checkY
    Key: GLDQAMYCGOIJDV-UHFFFAOYSA-N checkY
  • 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[1]
C7H6O4
Molar mass154.121 g·mol−1
AppearanceColorless solid
Density1.542 g/cm3 (20 °C)
Melting point205 °C (401 °F; 478 K)
soluble
Solubility inethanolsoluble
Solubility indiethyl ethersoluble
Solubility inacetonesoluble
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

2,3-Dihydroxybenzoic acid is adihydroxybenzoic acid, a type of organic compound. It occurs naturally in various plants, bacteria, and fungi.

Uses

[edit]

It is a potentially usefuliron-chelating drug and hasantimicrobial properties.[2][3][medical citation needed]

Occurrence

[edit]

It is found inPhyllanthus acidus[citation needed] and in the aquatic fernSalvinia molesta.[4] It is also abundant in the fruits ofFlacourtia inermis.[2]

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

2,3-Dihydroxybenzoic acid is also a product of humanaspirin metabolism.[6]

References

[edit]
  1. ^Haynes, William M., ed. (2016). "3".CRC Handbook of Chemistry and Physics(PDF) (97th ed.).CRC Press. p. 190.ISBN 9781498754293.
  2. ^abGraziano, 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.
  3. ^George, Shibumon; PJ, Benny; Kuriakose, Sunny; George, Cincy (2011)."Antibiotic activity of 2,3-dihydroxybenzoic acid isolated fromFlacourtia inermis fruit against multidrug resistant bacteria"(PDF).Asian Journal of Pharmaceutical and Clinical Research.4 (1).
  4. ^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.
  5. ^O'Brien, I. G.; Cox, G. B.; Gibson, F. (1970). "Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed byEscherichia coli".Biochimica et Biophysica Acta (BBA) - General Subjects.201 (3):453–60.doi:10.1016/0304-4165(70)90165-0.PMID 4908639.
  6. ^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.
Phenolic acids (C6-C1) and their glycosides
Monohydroxybenzoic acids
Glycosides
Alkylated
Dihydroxybenzoic acids
Alkylated
Trihydroxybenzoic acids
Glycosides
Alkylated
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