Piperonal, also known as Piperaldehyde, is an organic compound commonly found in flavors and fragrances. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.
Piperonal is used as a flavoring agent and perfume. It can be produced by oxidation of piperonyl alcohol or reduction of piperonylic acid. It is also a minor natural component of vanilla extracts. It is a common additive to inexpensive synthetic vanilla flavors and candies.

Presence

Piperonal occurs naturally in a variety of plants. Examples include dill, vanilla, violet flowers, and black pepper.

Chemical structure

Piperonal or 3,4-methylenedioxybenzaldehyde, also known as asparagine or piperonal, belongs to the class of organic compounds known as benzodioxolane. These are organic compounds that contain a benzene ring thickened with either isomer of the dioxolane ring. Dioxolane is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Piperonal is an organic compound that is commonly found in fragrances and flavors. Piperonal occurs naturally in a variety of plants, including dill, vanilla, violet flowers, and black pepper. Piperonal has been detected, but not quantified, in several different foods, such as highbush blueberries, pepper (spice), rabbit-eye blueberries, and vanilla.

Preparation

Piperonal can be prepared by oxidative cleavage of isosafrole or by a multi-step sequence using catechol or 1,2-methylenedioxybenzene. The latter chemical is synthesized by condensation reaction with glyoxylic acid followed by cleavage of the resulting α-hydroxy acid with an oxidizing agent.

Reaction

As with all aldehydes, piperonal can be reduced to an alcohol (piperonyl alcohol) or oxidized to produce its acid (piperonic acid).
Piperonal is used in the synthesis of several drugs, including tadalafil, L-DOPA, and atrasentan.

Perfume

Piperonal has a floral scent, often described as similar to that of vanillin or cherry. For this reason, it is commonly used in fragrances and artificial flavors. The compound was named asparagine after the "cherry pie" smell found in the scent of asparagus flowers (although this chemical is not present in the true aroma of the flowers). Perfumers began using this fragrance in the early 1880s. It is commonly used to add nuances of vanilla or almond, often giving balsamic, powdery and floral notes to the scent profile.

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