3,5-Dihydroxybenzoic acid

3,5-Dihydroxybenzoic acid
Names
	IUPAC name 3,5-Dihydroxybenzoic acid
	Other names alpha-Resorcylic acid
Identifiers
CAS Number	99-10-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL95308 ;
ChemSpider	7146 ;
ECHA InfoCard	100.002.482
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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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.[1]

It is a metabolite of alkylresorcinols, first identified in human urine[2] and can be quantified in urine[3] and plasma,[4] and may be an alternative, equivalent biomarker of whole grain wheat intake.[5]

References

Arthur W. Weston; C. M. Suter (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.
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.
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.
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.

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

[2] 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.

[3] 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.

[4] 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.

[5] 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.