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2,4-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
Chemical formula	C₇H₆O₄
Molar mass	154.12 g/mol
Melting point	229 °C (444 °F; 502 K)^[2]
Acidity (pK_a)	3.11, 8.55, 14.0^[1]
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). Y verify (what is ^YN ?) 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.^[4] Synthesis from resorcinol is via the Kolbe-Schmitt reaction.^[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]

References[edit]

^ Haynes, p. 5.91

^ Haynes, p. 3.190

^ GHS: GESTIS 492493

^ Resorcyclic acid on merriam-webster on-line dictionary

^ Becker, Heinz G. O., ed. (1993). Organikum: organisch-chemisches Grundpraktikum (in German) (19th (rev. and expanded) ed.). Leipzig: Johann Ambrosius Barth [de]. 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.