2,3-Dihydroxybenzoic acid

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 InfoCard 100.005.582 Edit 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
C7H6O4
Molar mass 154.121 g·mol−1
Appearance Colorless 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).
checkY verify (what is checkY☒N ?)

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]

References

[edit]
  1. ^ a b 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.
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