2,3-Dihydroxybenzoic acid

Last updated
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)
Abbreviations
  • 2,3-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 [1]
C7H6O4
Molar mass 154.121 g·mol−1
AppearanceColorless solid
Density 1.542 g/cm3 (20 °C)
Melting point 205 °C (401 °F; 478 K)
soluble
Solubility in ethanol soluble
Solubility in diethyl ether soluble
Solubility in acetone soluble
Related compounds
Related compounds
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 dihydroxybenzoic acid, a type of organic compound. It occurs naturally in various plants, bacteria, and fungi.

Contents

Uses

It is a potentially useful iron-chelating drug and has antimicrobial properties. [2] [3] [ medical citation needed ]

Occurrence

It is found in Phyllanthus acidus [ citation needed ] and in the aquatic fern Salvinia molesta . [4] It is also abundant in the fruits of Flacourtia inermis . [2]

The colorless solid occurs naturally, being formed via the shikimate pathway.[ citation needed ] 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. [5]

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

References

  1. ↑ Haynes, William M., ed. (2016). "3". CRC Handbook of Chemistry and Physics (PDF) (97th ed.). CRC Press. p. 190. ISBN   9781498754293.
  2. 1 2 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.
  3. ↑ 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).
  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 by Escherichia 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.
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