3,5-Dihydroxybenzoic acid

3,5-Dihydroxybenzoic acid
	Chemical structure of 3,5-dihydroxybenzoic acid
Names
	Preferred IUPAC name 3,5-Dihydroxybenzoic acid
	Other names α-Resorcylic acid
Identifiers
CAS Number	99-10-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39912;
ChEMBL	ChEMBL95308 ;
ChemSpider	7146 ;
ECHA InfoCard	100.002.482
EC Number	202-730-7;
IUPHAR/BPS	5783;
PubChem CID	7424;
UNII	2WC5LMO6L1 ;
CompTox Dashboard (EPA)	DTXSID8059184 ;
	InChI InChI=1S/C7H6O4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H,(H,10,11) Key: UYEMGAFJOZZIFP-UHFFFAOYSA-N ;
	SMILES C1=C(C=C(C=C1O)O)C(=O)O;
Properties
Chemical formula	C7H6O4
Molar mass	154.121 g·mol−1
Melting point	235.3 °C (455.5 °F; 508.4 K)
Solubility in water	soluble
Solubility in acetone	soluble
Solubility in ethanol	very soluble
Solubility in diethyl ether	very soluble
Acidity (pKa)	4.04
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds	2,3-Dihydroxybenzoic acid; 2,4-Dihydroxybenzoic acid; 2,5-Dihydroxybenzoic acid; 2,6-Dihydroxybenzoic acid; 3,4-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

3,5-Dihydroxybenzoic acid (α-resorcylic acid) is a dihydroxybenzoic acid. It is a colorless solid.

Preparation and occurrence

It is prepared by disulfonation of benzoic acid followed by hydrolysis of the disulfonate.^[3]

It is a metabolite of alkylresorcinols, first identified in human urine and can be quantified in urine and plasma, and may be an alternative, equivalent biomarker of whole grain wheat intake.^[4]

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.
^ Weston, Arthur W.; Suter, C. M. (1941). "3,5-Dihydroxybenzoic Acid". Org. Synth. 21: 27. doi:10.15227/orgsyn.021.0027.
^ Ross, A.B.; Åman, P.; Kamal-Eldin, A. (2004). "Identification of cereal alkylresorcinol metabolites in human urine—potential biomarkers of wholegrain wheat and rye intake". Journal of Chromatography B. 809 (1): 125–130. doi:10.1016/j.jchromb.2004.06.015. PMID 15282102.

[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] Weston, Arthur W.; Suter, C. M. (1941). "3,5-Dihydroxybenzoic Acid". Org. Synth. 21: 27. doi:10.15227/orgsyn.021.0027.

[4] Ross, A.B.; Åman, P.; Kamal-Eldin, A. (2004). "Identification of cereal alkylresorcinol metabolites in human urine—potential biomarkers of wholegrain wheat and rye intake". Journal of Chromatography B. 809 (1): 125–130. doi:10.1016/j.jchromb.2004.06.015. PMID 15282102.

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