2,4-Dihydroxybenzoic acid

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42094;
ChEMBL	ChEMBL328910 ;
ChemSpider	1446 ;
DrugBank	DB02839 ;
ECHA InfoCard	100.001.770
PubChem CID	1491;
UNII	LU39SC9JYL ;
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) Key: UIAFKZKHHVMJGS-UHFFFAOYSA-N ;
	SMILES C1=CC(=C(C=C1O)O)C(=O)O;
Properties
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;
Hazards
	GHS labelling:
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). verify (what is ?) Infobox references

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

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]

References

^ Haynes, William M., ed. (2016). "5". CRC Handbook of Chemistry and Physics (PDF) (97th ed.). CRC Press. p. 91. ISBN 9781498754293.
^ Haynes, William M., ed. (2016). "3". CRC Handbook of Chemistry and Physics (PDF) (97th ed.). CRC Press. p. 190. ISBN 9781498754293.
^ GHS: GESTIS 492493
^ Becker, Heinz G.O., ed. (1993). Organikum: organisch-chemisches Grundpraktikum (in German) (19th (rev. and expanded) ed.). Leipzig: Johann Ambrosius Barth. pp. 351–352. ISBN 978-3-335-00343-4.
^ Seeram, Navindra P.; Bourquin, Leslie D.; Nair, Muraleedharan G. (2001). "Degradation Products of Cyanidin Glycosides from Tart Cherries and Their Bioactivities". Journal of Agricultural and Food Chemistry. 49 (10): 4924–4929. doi:10.1021/jf0107508. PMID 11600045.
^ Zhang, Kai; Zuo, Yuegang (2004). "GC-MS Determination of Flavonoids and Phenolic and Benzoic Acids in Human Plasma after Consumption of Cranberry Juice". Journal of Agricultural and Food Chemistry. 52 (2): 222–227. doi:10.1021/jf035073r. PMID 14733499.

[1] Haynes, William M., ed. (2016). "5". CRC Handbook of Chemistry and Physics (PDF) (97th ed.). CRC Press. p. 91. ISBN 9781498754293.

[crc-2] Haynes, William M., ed. (2016). "3". CRC Handbook of Chemistry and Physics (PDF) (97th ed.). CRC Press. p. 190. ISBN 9781498754293.

[3] GHS: GESTIS 492493

[4] Becker, Heinz G.O., ed. (1993). Organikum: organisch-chemisches Grundpraktikum (in German) (19th (rev. and expanded) ed.). Leipzig: Johann Ambrosius Barth. pp. 351–352. ISBN 978-3-335-00343-4.

[5] Seeram, Navindra P.; Bourquin, Leslie D.; Nair, Muraleedharan G. (2001). "Degradation Products of Cyanidin Glycosides from Tart Cherries and Their Bioactivities". Journal of Agricultural and Food Chemistry. 49 (10): 4924–4929. doi:10.1021/jf0107508. PMID 11600045.

[6] Zhang, Kai; Zuo, Yuegang (2004). "GC-MS Determination of Flavonoids and Phenolic and Benzoic Acids in Human Plasma after Consumption of Cranberry Juice". Journal of Agricultural and Food Chemistry. 52 (2): 222–227. doi:10.1021/jf035073r. PMID 14733499.

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