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;
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	154.12 g/mol
Melting point	229 °C (444 °F; 502 K)[1]
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
	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 (Resochin,[4] sontochin,[4] SN-7619,[4] 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.[5]

It is a degradation product of cyanidin glycosides from tart cherries in cell cultures.[6] It is also a metabolite found in human plasma after cranberry juice consumption.[7]

Resochin is especially effective against avian malaria. Because the initial testing during the chemical development process used avian malaria its efficacy was recognised immediately.[4]

References

Haynes, p. 3.190
Haynes, p. 5.91
GHS: GESTIS 492493
Jensen, Markus; Mehlhorn, Heinz (2009-07-11). Ryan, Una; Walochnik, Julia (eds.). "Seventy-five years of Resochin® in the fight against malaria". Parasitology Research. Springer. 105 (3): 609–627. doi:10.1007/s00436-009-1524-8. PMID 19593586. S2CID 8037461.
Resorcyclic acid on merriam-webster on-line dictionary
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.

Cited sources

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

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[crc-1] Haynes, p. 3.190

[2] Haynes, p. 5.91

[3] GHS: GESTIS 492493

[Jensen-Mehlhorn-2009-4] Jensen, Markus; Mehlhorn, Heinz (2009-07-11). Ryan, Una; Walochnik, Julia (eds.). "Seventy-five years of Resochin® in the fight against malaria". Parasitology Research. Springer. 105 (3): 609–627. doi:10.1007/s00436-009-1524-8. PMID 19593586. S2CID 8037461.

[5] Resorcyclic acid on merriam-webster on-line dictionary

[6] 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.

[7] 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.