3,5-Dihydroxyphenylpropionoic acid

3,5-Dihydroxyphenylpropionoic acid is a metabolite of alkylresorcinols, first identified in human urine[1] and can be quantified in urine[2] and plasma,[3] and may be an alternative, equivalent biomarker of whole grain wheat intake.[4]

3,5-Dihydroxyphenylpropionoic acid
Chemical structure of 3,5-dihydroxyphenylpropionoic acid
Names
Preferred IUPAC name
3-(3,5-Dihydroxyphenyl)propanoic acid
Other names
DHPPA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.189.620
KEGG
UNII
  • InChI=1S/C9H10O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h3-5,10-11H,1-2H2,(H,12,13)
    Key: ITPFIKQWNDGDLG-UHFFFAOYSA-N
  • InChI=1/C9H10O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h3-5,10-11H,1-2H2,(H,12,13)
    Key: ITPFIKQWNDGDLG-UHFFFAOYAE
  • C1=C(C=C(C=C1O)O)CCC(=O)O
Properties
C9H10O4
Molar mass 182.175 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. 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.
  2. 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.
  3. 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.
  4. 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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