3,5-Dihydroxybenzoic acid

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

3,5-Dihydroxybenzoic acid

Names
Preferred IUPAC name 3,5-Dihydroxybenzoic acid
Other names α-Resorcylic acid
Identifiers
CAS Number	99-10-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:39912
ChEMBL	ChEMBL95308 Y
ChemSpider	7146 Y
ECHA InfoCard	100.002.482
EC Number	202-730-7
IUPHAR/BPS	5783
PubChem CID	7424
UNII	2WC5LMO6L1 Y
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) Y Key: UYEMGAFJOZZIFP-UHFFFAOYSA-N Y
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)[1]
Acidity (pKa)	4.04[2]
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	Gallic acid; 4-Hydroxybenzoic acid; Phloroglucinol
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

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^[4] and can be quantified in urine^[5] and plasma,^[6] and may be an alternative, equivalent biomarker of whole grain wheat intake.^[7]

References

1. Haynes, p. 3.190
2. Haynes, p. 5.91
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.
5. Koskela, A.; Linko-Parvinen, A. -M.; Hiisivuori, P.; Samaletdin, A.; Kamal-Eldin, A.; Tikkanen, M. J.; Adlercreutz, H. (2007). "Quantification of Alkylresorcinol Metabolites in Urine by HPLC with Coulometric Electrode Array Detection". Clinical Chemistry. 53 (7): 1380–1383. doi:10.1373/clinchem.2006.084764. PMID 17495018.
6. Koskela, A.; Samaletdin, A.; Aubertin-Leheudre, M. N.; Adlercreutz, H. (2008). "Quantification of Alkylresorcinol Metabolites in Plasma by High-Performance Liquid Chromatography with Coulometric Electrode Array Detection". Journal of Agricultural and Food Chemistry. 56 (17): 7678–7681. CiteSeerX 10.1.1.533.1473. doi:10.1021/jf801252s. PMID 18690683.
7. Aubertin-Leheudre, M.; Koskela, A.; Marjamaa, A.; Adlercreutz, H. (2008). "Plasma Alkylresorcinols and Urinary Alkylresorcinol Metabolites as Biomarkers of Cereal Fiber Intake in Finnish Women". Cancer Epidemiology, Biomarkers & Prevention. 17 (9): 2244–2248. doi:10.1158/1055-9965.EPI-08-0215. PMID 18768490.

Cited sources

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