Isolation and identification of mercapturic acids of cinnamic aldehyde and cinnamyl alcohol from urine of female rats

Arch Toxicol. 1981 Nov;49(1):57-64. doi: 10.1007/BF00352072.

Abstract

Rats dosed with cinnamic aldehyde (I) excreted two mercapturic acids in the urine. The major one was identified as N-acetyl-S-(1-phenyl-3-hydroxypropyl)cysteine (V). The minor one was identified as N-acetyl-S-(1-phenyl-2-carboxy ethyl)cysteine (VI). The ratio appeared to be V : VI = 4 : 1. The hydroxy mercapturic acid (V) was also isolated from urine of rats dosed with cinnamyl alcohol (II). The total mercapturic acid excretion as percentage of the dose was 14.8 +/- 1.9% for cinnamic aldehyde (250 mg/kg) (n = 4) and 8.8 +/- 1.7% for cinnamyl alcohol (n = 4) (125 mg/kg). Inhibition of the alcohol dehydrogenase by pyrazole (206 mg/kg) diminished the thioether excretion of cinnamyl alcohol to 3.3 +/- 1.4% of the dose (n = 8). Cinnamic aldehyde has been proposed to be an intermediate in the mercapturic acid formation of cinnamyl alcohol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Propanol / metabolism
  • Acetylcysteine / analogs & derivatives*
  • Acetylcysteine / urine
  • Acrolein / analogs & derivatives
  • Acrolein / metabolism*
  • Aldehydes / metabolism*
  • Animals
  • Female
  • Mass Spectrometry
  • Propanols
  • Rats

Substances

  • Aldehydes
  • Propanols
  • N-acetyl-S-(1-phenyl-3-hydroxypropyl)cysteine
  • N-acetyl-S-(1-phenyl-2-carboxyethyl)cysteine
  • Acrolein
  • 1-Propanol
  • cinnamaldehyde
  • cinnamyl alcohol
  • Acetylcysteine