Геліотроп

Heliotropin is another name for piperonal, an organic compound commonly found in fragrances and flavors. The compound was named heliotropin after the 'cherry pie' notes found in the heliotrope flower's fragrance, even though the chemical is not present in the flower's true aroma.

Explore all seven extraits in the Discovery Set.

The plant

The species is native to Bolivia, Colombia and Peru. It is a bushy, evergreen, short-lived shrub that grows to 1.2 m tall and broad, with dense clusters of bright purple flowers. The plant contains poisonous pyrrolizidine alkaloids in addition to its fragrances. The seeds are poisonous, and heliotropes are toxic to horses and can induce liver failure in equines.

As a perennial, it is hardy in zones 10 to 11, and requires wintering indoors in zones 9 or colder. The cultivar 'Marine' has large, highly fragrant dark purple flowerheads up to 15 cm in diameter and burgundy leaves.

Chemistry and occurrence

Piperonal has the formula C₈H₆O₃ and the IUPAC name 1,3-benzodioxole-5-carbaldehyde. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin. Piperonal naturally occurs in various plants, for example dill, violet flowers and black pepper.

Like all aldehydes, piperonal can be reduced to its alcohol, piperonyl alcohol, or oxidized to give its acid, piperonylic acid. It can be used in the synthesis of some pharmaceutical drugs including tadalafil, L-DOPA and atrasentan. It is soluble in alcohol, benzyl benzoate, dipropylene glycol, fixed oils, isopropyl myristate and propylene glycol, and insoluble in paraffin oil and glycerin. Its solubility in water is 3500 mg/L at 25 °C (experimental).

Use in flavors

Piperonal is commonly used in flavors, where it adds hay-like, floral and powdery notes to a wide range of food preparations. It is used heavily in French vanilla flavors, in part as a replacement for coumarin, which is no longer GRAS. Piperonyl alcohol forms esters with aliphatic acids; several of these esters, including piperonyl acetate and piperonyl isobutyrate, are used in flavorings to give floral, fruity notes.

DEA precursor status

Piperonal is a List I chemical, among the chemicals designated as listed chemicals by the US Drug Enforcement Administration. Because of their role in the production of MDMA, safrole, isosafrole and piperonal are Category I precursors under a regulation of the European Community. In Brazil, piperonal is in Class D1, drug precursors.