3,5-Dihydroxybenzoic acid

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)
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	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). 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^[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

^ Haynes, p. 5.91
^ Haynes, p. 3.190
^ 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 15282102.125-130&rft.date=2004&rft_id=info:doi/10.1016/j.jchromb.2004.06.015&rft_id=info:pmid/15282102&rft.aulast=Ross&rft.aufirst=A. B.&rft.au=Åman, P.&rft.au=Kamal-Eldin, A.&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">
^ 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 17495018.1380-1383&rft.date=2007&rft_id=info:doi/10.1373/clinchem.2006.084764&rft_id=info:pmid/17495018&rft.aulast=Koskela&rft.aufirst=A.&rft.au=Linko-Parvinen, A. -M.&rft.au=Hiisivuori, P.&rft.au=Samaletdin, A.&rft.au=Kamal-Eldin, A.&rft.au=Tikkanen, M. J.&rft.au=Adlercreutz, H.&rft_id=https://doi.org/10.1373%2Fclinchem.2006.084764&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">
^ 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 18690683.7678-7681&rft.date=2008&rft_id=https://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.533.1473#id-name=CiteSeerX&rft_id=info:pmid/18690683&rft_id=info:doi/10.1021/jf801252s&rft.aulast=Koskela&rft.aufirst=A.&rft.au=Samaletdin, A.&rft.au=Aubertin-Leheudre, M. N.&rft.au=Adlercreutz, H.&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">
^ 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 18768490.2244-2248&rft.date=2008&rft_id=info:doi/10.1158/1055-9965.EPI-08-0215&rft_id=info:pmid/18768490&rft.aulast=Aubertin-Leheudre&rft.aufirst=M.&rft.au=Koskela, A.&rft.au=Marjamaa, A.&rft.au=Adlercreutz, H.&rft_id=https://doi.org/10.1158%2F1055-9965.EPI-08-0215&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">

Cited sources

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

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[1] Haynes, p. 5.91

[crc-2] Haynes, p. 3.190

[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 15282102.125-130&rft.date=2004&rft_id=info:doi/10.1016/j.jchromb.2004.06.015&rft_id=info:pmid/15282102&rft.aulast=Ross&rft.aufirst=A. B.&rft.au=Åman, P.&rft.au=Kamal-Eldin, A.&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">

[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 17495018.1380-1383&rft.date=2007&rft_id=info:doi/10.1373/clinchem.2006.084764&rft_id=info:pmid/17495018&rft.aulast=Koskela&rft.aufirst=A.&rft.au=Linko-Parvinen, A. -M.&rft.au=Hiisivuori, P.&rft.au=Samaletdin, A.&rft.au=Kamal-Eldin, A.&rft.au=Tikkanen, M. J.&rft.au=Adlercreutz, H.&rft_id=https://doi.org/10.1373%2Fclinchem.2006.084764&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">

[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 18690683.7678-7681&rft.date=2008&rft_id=https://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.533.1473#id-name=CiteSeerX&rft_id=info:pmid/18690683&rft_id=info:doi/10.1021/jf801252s&rft.aulast=Koskela&rft.aufirst=A.&rft.au=Samaletdin, A.&rft.au=Aubertin-Leheudre, M. N.&rft.au=Adlercreutz, H.&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">

[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 18768490.2244-2248&rft.date=2008&rft_id=info:doi/10.1158/1055-9965.EPI-08-0215&rft_id=info:pmid/18768490&rft.aulast=Aubertin-Leheudre&rft.aufirst=M.&rft.au=Koskela, A.&rft.au=Marjamaa, A.&rft.au=Adlercreutz, H.&rft_id=https://doi.org/10.1158%2F1055-9965.EPI-08-0215&rfr_id=info:sid/en.wikipedia.org:3,5-Dihydroxybenzoic acid" class="Z3988">

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