University of North Florida
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Stuart Chalk, Ph.D.
Department of Chemistry
University of North Florida
Phone: 1-904-620-1938
Fax: 1-904-620-3535
Email: schalk@unf.edu
Website: @unf

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Vanillylmandelic acid

  • IUPAC Name: 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
  • Molecular Formula: C9H10O5
  • CAS Registry Number: 55-10-7
  • InChI: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
  • InChI Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N

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Citations 3

"Catalytic-polarographic Determination Of Vanillylmandelic Acid In Urine A Continuous De-oxygenation-flow Injection System"
Analyst 1987 Volume 112, Issue 11 Pages 1593-1596
Teiji Kakizaki, Kiyoshi Hasebe and Hitoshi Yoshida

Abstract: Test solution (25 µL) was injected into a carrier stream (1.6 mL min-1) 0.1 M in formic acid, 1 mM in KBrO3 and 1 µM in sodium molybdate and the resulting product stream was passed through a deoxygenation unit (cf. Trojanek and Holub, Anal. Chim. Acta, 1980, 121, 23) before measurement of the catalytic reduction current due to 4-hydroxy-3-methoxymandelic acid(I), at -0.4 V (vs. Ag - AgCl), at a static-mercury-drop electrode. Measurements could be made in either sampled DC or normal pulse polarographic mode and the respective calibration graphs were rectilinear from 0.1 to 0.6 and 0.1 to 1.4 µg mL-1 of I; the respective coefficient of variation (at 0.4 µg mL-1) and limits of detection were 1.81 and 2.55% (n = 5) and 5.7 and 10 ng mL-1. The effects of 12 potential interferents in urine were generally smaller with normal pulse polarography. The method has been successfully applied to urine samples after cleanup by extraction of I into ethyl acetate (cf. Hasebe et al., Anal. Chem., 1987, 59, 373); the results for 30 samples correlated well (r = 0.9827) with those obtained by HPLC with electrochemical detection.
Urine Electrode Polarography Interferences Catalysis Method comparison

"High Performance Liquid Chromatographic Determination Of Total Catecholamines And Metabolites In Human Urine By Application Of The Fluorescence Derivatization Method For Their Free Form"
Anal. Sci. 1993 Volume 9, Issue 4 Pages 537-540
H. NOHTA, H.-K. JEON, M. KAI and Y. OHKURA

Abstract: Urine was hydrolyzed with 1 M HClO4, 30 mM Na2EDTA and 0.1 M reduced glutathione at 100°C for 20 min to determine the total amino-compounds (TAC) and for 50 min to determine the total acidic and alcoholic compounds (TAAC). The internal standard, 30 µM isoproterenol was added prior to hydrolysis for TAC and after for TAAC, which after clarification (described), were separated by HPLC (cf. Anal. Biochem., 1992, 200, 332) and identified by post-column derivatization using periodate oxidation followed by fluorescence detection with meso-1,2-diphenylethylenediamine. Calibration graphs were linear from 10^-3000 pmol of vanillylmandelic acid and 4-hydroxy-3-methoxyphenylethylene glycol (I), and from 0.2-200 pmol of norepinephrine (II), epinephrine, dopamine, normetanephrine, metanephrine, 3-methoxytyramine, 3,4-dihydroxyphenylacetic acid, and homovanillic acid. The corresponding detection limits were 60, 90, 0.3, 0.7, 2, 0.4, 1, 2, 5, and 5 pmol/ml, in urine. The RSD were 4.5 and 5% for I and II, respectively, and 3% for all the others.
Urine Fluorescence HPLC Post-column derivatization

"Urinary 4-hydroxy-3-methoxymandelic Acid As Measured By Liquid Chromatography, With One-line Post-column Reaction"
Clin. Chem. 1979 Volume 25, Issue 7 Pages 1234-1238
JG Flood, M Granger and RB McComb

Abstract: We describe a method for measurement of 3-methoxy-4-hydroxymandelic acid (vanillylmandelic acid, VMA) in urine. After the pH of the urine is adjusted to 2.7 and the sample is filtered, exactly 15 µL is injected onto a C-18 reversed-phase column. VMA is eluted from the column with 10 mmol/L phosphate buffer, pH 2.7, containing 30 mL of acetonitrile per liter. The eluate stream is combined with alkaline periodate and then passed through a 60°C water bath. The VMA is completely oxidized to vanillin, which is detected and quantitiated by its absorbance at 360 nm. No deterioration of the column was noted after 167 such injections of urine samples. Long-term control data indicate a CV of 12 and 10% at VMA concentrations of 1.5 and 5.8 mg/L, respectively. Although results correlate well (r = 0.976) with those by the method of Pisano et al. [Clin. Chim. Acta 7, 285 (1962)], they average 10% lower. Of 20 compounds tested, only methyl dopa interfered with the procedure as described.
Urine Clinical analysis HPLC Post-column derivatization Interferences