3,5-Dihydroxybenzoic acid

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3,5-Dihydroxybenzoic acid
Chemical structure of 3,5-dihydroxybenzoic acid
Names
IUPAC name
3,5-Dihydroxybenzoic acid
Other names
alpha-Resorcylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.482
Properties
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[edit]

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[edit]

  1. ^ Arthur W. Weston, C. M. Suter (1941). "3,5-Dihydroxybenzoic Acid". Org. Synth. 21: 27. doi:10.15227/orgsyn.021.0027.CS1 maint: Uses authors parameter (link)
  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.