2,4-Dihydroxybenzoic acid

2,4-Dihydroxybenzoic acid (β-resorcylic acid) is a dihydroxybenzoic acid.

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2,4-Dihydroxybenzoic acid

Names
Preferred IUPAC name 2,4-Dihydroxybenzoic acid
Other names β-Resorcylic acid β-Resorcinolic acid p-Hydroxysalicylic acid 2,4-DHBA
Identifiers
CAS Number	89-86-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:42094
ChEMBL	ChEMBL328910 Y
ChemSpider	1446 Y
DrugBank	DB02839 Y
ECHA InfoCard	100.001.770
PubChem CID	1491
UNII	LU39SC9JYL Y
CompTox Dashboard (EPA)	DTXSID0025074
InChI InChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11) Y Key: UIAFKZKHHVMJGS-UHFFFAOYSA-N Y
SMILES C1=CC(=C(C=C1O)O)C(=O)O
Properties[1]
Chemical formula	C7H6O4
Molar mass	154.121 g·mol−1
Melting point	229 °C (444 °F; 502 K)
Solubility in water	soluble
Solubility in ethanol	soluble
Solubility in diethyl ether	soluble
Solubility in benzene	soluble
Acidity (pKa)	3.11 8.55 14.0[2]
Hazards
GHS labelling:[3]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P280, P302+P352, P305+P351+P338
Related compounds
Related compounds	2,3-Dihydroxybenzoic acid 2,5-Dihydroxybenzoic acid 2,6-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid 3,5-Dihydroxybenzoic acid
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

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As a resorcylic acid, it is one of the three isomeric crystalline acids that are both carboxyl derivatives of resorcinol and dihydroxy derivatives of benzoic acid. Synthesis from resorcinol is via the Kolbe-Schmitt reaction.^[4]

It is a degradation product of cyanidin glycosides from tart cherries in cell cultures.^[5] It is also a metabolite found in human plasma after cranberry juice consumption.^[6]