2,3-Dihydroxybenzoic acid

2,3-Dihydroxybenzoic acid
Names
	IUPAC name 2,3-Dihydroxybenzoic acid
	Other names DHBA; 2,3-DHB
Identifiers
CAS Number	303-38-8 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL1432 ;
ECHA InfoCard	100.005.582
KEGG	C00196 ;
CompTox Dashboard (EPA)	DTXSID70858712 ;
	InChI InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) Key: GLDQAMYCGOIJDV-UHFFFAOYSA-N ; 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
Chemical formula	C7H6O4
Molar mass	154.121 g·mol−1
Appearance	Colorless solid
Melting point	204-206 °C
Solubility in water	low
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

References

^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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