Piperonal (Pip)

Piperonal is an organic compound that is commonly found in fragrances and flavors. The molecule is structurally related to benzaldehyde and vanillin. It exists as a white or colorless solid. Heliotropine occurs naturally in a range of plants including dill, violet flowers, black pepper and others. As is vanillin, it is also found in vanilla. Piperonal is prepared by oxidation of isosafrole, which occurs naturally. It is also prepared in a multistep sequence from catechol or 1,2-methylenedioxybenzene by condensation with glyoxylic acid. Reduction gives piperonyl alcohol and oxidation gives piperonylic acid. Piperonal may be used in the synthesis of 3,4-methylenedioxyamphetamine (MDA) via the substituted nitrostyrene via Knoevenagel condensation. This intermediate can then be reduced by a strong reducing agent such as lithium aluminium hydride (LiAlH4) to yield MDA.