2,3-Dihydroxybenzoic acid

2,3-Dihydroxybenzoic acid
2,3-Dihydroxybenzoic acid
CAS number 303-38-8 YesY
PubChem 19
ChemSpider 18
DrugBank DB01672
KEGG C00196 YesY
Jmol-3D images Image 1
Image 2
Molecular formula C7H6O4
Molar mass 154.12 g mol−1
Exact mass 154.026609 u
Appearance Colorless solid
Melting point

204-206 °C

Solubility in water low
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,3-Dihydroxybenzoic acid is a dihydroxybenzoic acid, a type of organic compound. The colourless solid occurs naturally, being formed via the chorismic acid 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 via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine.[1][2] It is a potentially useful iron-chelating drug.[3]

2,3-Dihydroxybenzoic acid is also a product of human aspirin metabolism.[4]


  1. ^ I. G. O'Brien, G. B. Cox, F. Gibson (1970). "Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli". Biochimica et Biophysica Acta 201 (3): 453–60. PMID 4908639. 
  2. ^ Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in Aerobacter aerogenes and Escherichia coli. I.G. Young and F. Gibson, Biochimica et Biophysica Acta (BBA) - General Subjects, Volume 177, Issue 3, 6 May 1969, pages 401-411, doi:10.1016/0304-4165(69)90302-X
  3. ^ The identification of 2,3-dihroxybenzoic acid as a potentially useful iron-chelating drug. J. H. Graziano, R. W. Grady and A. Cerami, JPET, September 1974, vol. 190, no. 3, pages 570-575, http://jpet.aspetjournals.org/content/190/3/570.short
  4. ^ 2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism. Martin Grootveld and Barry Halliwell, Biochemical Pharmacology, Volume 37, Issue 2, 15 January 1988, pages 271-280, doi:10.1016/0006-2952(88)90729-0

Wikimedia Foundation. 2010.

Игры ⚽ Поможем решить контрольную работу

Look at other dictionaries:

  • Dihydroxybenzoic acid — Dihydroxybenzoic acids (DHBA) are a type of phenolic acids. There are six main compounds, having all the same molecular formula C7H6O4. Those are: 2,3 Dihydroxybenzoic acid (2 Pyrocatechuic acid) 2,4 Dihydroxybenzoic acid (β Resorcylic acid) 2,5… …   Wikipedia

  • 2,4-Dihydroxybenzoic acid — IUPAC name 2,4 dihydroxybenzoic ac …   Wikipedia

  • dihydroxybenzoic acid — noun Any of six isomeric dihydroxy derivatives of benzoic acid See Also: dihydroxybenzoate …   Wiktionary

  • Orsellinic acid — IUPAC name …   Wikipedia

  • Monohydroxybenzoic acid — may refer to any of three isomeric phenolic acids: Salicylic acid (2 hydroxybenzoic acid, o hydroxybenzoic acid) 3 Hydroxybenzoic acid (m hydroxybenzoic acid) p Hydroxybenzoic acid (4 hydroxybenzoic acid) Monohydroxybenzoic acids can be degraded… …   Wikipedia

  • Salicylic acid — Salicylic acid …   Wikipedia

  • Gallic acid — IUPAC name …   Wikipedia

  • Homogentisic acid — IUPAC name (2,5 Dihydroxyphenyl)acetic acid …   Wikipedia

  • 4-Hydroxybenzoic acid — IUP …   Wikipedia

  • 3-Hydroxybenzoic acid — IUPAC name 3 Hydroxybenzoic acid …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”