2,3-Dihydroxybenzoic acid

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

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
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) Y
    Key: GLDQAMYCGOIJDV-UHFFFAOYSA-N Y
  • 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
SMILES
  • 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)
Melting point 205 °C (401 °F; 478 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.

It is a potentially useful iron-chelating drug and has antimicrobial properties.

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

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