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Optimized synthesis of four isotopically labeled ( 13 C‐enriched) phenolic acids via a malonic acid condensation
Author(s) -
Robbins Rebecca J.,
Schmidt Walter F.
Publication year - 2004
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.869
Subject(s) - chemistry , malonic acid , isotope dilution , caffeic acid , condensation , mass spectrometry , ferulic acid , organic chemistry , chromatography , antioxidant , physics , thermodynamics
Four isotopically ( 13 C)‐labeled phenolic acids (caffeic [M + 3], sinapic [M + 2], p ‐coumaric [M + 6] and ferulic [M + 6] acids) were synthesized via a simple one‐step malonic acid condensation with a series of aldehydes. The aldehydes and the malonic acid were variously labeled and unlabeled to vary the enriched sites. 13 C and 1 H NMR analyses together confirmed the labeled positions. LC/MS confirmed the masses. These acids are intended for use as internal standards for isotope dilution mass spectrometry (IDMS). Copyright © 2004 John Wiley & Sons, Ltd.