An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

• Kirsti Parikka and
• Kristiina Wähälä

Beilstein J. Org. Chem. 2009, 5, No. 22, doi:10.3762/bjoc.5.22

• Helsinki, Finland 10.3762/bjoc.5.22 Abstract The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25

• alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the

• way for the immunochemical detection techniques of alkylresorcinols. Keywords: 5-n-alkylresorcinols; haptens; microwave assisted synthesis; Wittig reaction; Introduction 5-Alk(en)ylresorcinols and related compounds are phenolic lipids present in several families of plants (e.g. Gramineae