Acide 2,3-dihydroxybenzoïque

Acide 2,3-dihydroxybenzoïque
Image illustrative de l’article Acide 2,3-dihydroxybenzoïque
Identification
Nom UICPA acide 2,3-dihydroxybenzoïque
Synonymes

2,3-DHB

No CAS 303-38-8
No ECHA 100.005.582
No CE 206-139-5
No RTECS DG8576490
PubChem 1924847707
SMILES
InChI
Apparence solide incolore
Propriétés chimiques
Formule C7H6O4  [Isomères]
Masse molaire[2] 154,120 1 ± 0,007 2 g/mol
C 54,55 %, H 3,92 %, O 41,52 %,
pKa 2,914 à 25 °C[1]
Propriétés physiques
T° fusion 204-206 °C[3]
Précautions
SGH[3]
SGH07 : Toxique, irritant, sensibilisant, narcotique
H315, H319, H335, P261 et P305+P351+P338
Écotoxicologie
DL50 > 3 g·kg-1 (lapin, oral)[4]
LogP 1,2[1]
Unités du SI et CNTP, sauf indication contraire.
modifier 

L'acide 2,3-dihydroxybenzoïque (2,3-DHB) est un composé organique aromatique. C'est l'un des six isomères de l'acide dihydroxybenzoïque (DHB), constitué d'un cycle benzénique substitué par deux fonction alcool (phénol) et une fonction acide carboxylique. Il se présente sous la forme d'un solide incolore.

Il est biosynthétisé à partir de l'acide chorismique, lui-même synthétisé à partir de l'acide shikimique.

Il fait partie de nombreux sidérophores, molécules complexant fortement les ions fer facilitant son absorption chez les bactéries. Ce fait peut s'expliquer par sa structure : le 2,3-DHB est constitué d'un groupe catéchol qui lorsqu'il est déprotoné peut lier fortement des centres fer, et sa partie acide carboxylique permet de rattacher la molécule à de nombreux composés via une liaison amide. On peut citer parmi ces sidérophores l'entérobactine, un sidérophore à haute affinité qui contient trois substituants, dihydroxybenzoyle liés au depsitripeptide de la sérine[5].

Notes et références

  1. ↑ a et b (en) « Acide 2,3-dihydroxybenzoïque », sur ChemIDplus, consulté le 3 juillet 2011
  2. ↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  3. ↑ a b et c Fiche Sigma Aldrich, consultée le 3 juillet 2011
  4. ↑ Journal of Pharmacology and Experimental Therapeutics. Vol. 196, Pg. 478, 1976.
  5. ↑ (en) I. G. O'Brien, G. B. Cox, F. Gibson, « Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli », Biochimica et Biophysica Acta, vol. 201, no 3,‎ , p. 453–60 (PMID 4908639)

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