Piperonal

Piperonal

Names
IUPAC name 1,3-Benzodioxole-5-carbaldehyde
Other names Heliotropin; Heliotropine; Piperonyl aldehyde; Protocatechuic aldehyde methylene ether; 3,4-methylenedioxybenzaldehyde;
Identifiers
CAS Number	120-57-0 Y
ChEBI	CHEBI:8240 N
ChEMBL	ChEMBL271663 N
ChemSpider	13859497 N
Jmol 3D model	Interactive image Interactive image
UNII	KE109YAK00 Y
InChI InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2 N Key: SATCULPHIDQDRE-UHFFFAOYSA-N N
SMILES O=Cc1ccc2OCOc2c1 c1cc2c(cc1C=O)OCO2
Properties
Chemical formula	C8H6O3
Molar mass	150.13 g·mol−1
Appearance	Colorless crystals
Density	1.337 g/cm3
Melting point	37 °C (99 °F; 310 K)
Boiling point	263 °C (505 °F; 536 K)
Solubility in water	Soluble in 500 parts
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.

Natural occurrence

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

Preparation

Piperonal can be prepared by oxidizing isosafrole or by using a multistep sequence from catechol or 1,2-methylenedioxybenzene. Synthesis from the latter chemical is accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent. Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane.

Reactions

Piperonal, like all aldehydes, can be reduced to its alcohol (piperonyl alcohol) or oxidized to give its acid (piperonylic acid). Piperonal can be used to synthesize 3,4-methylenedioxyamphetamine (MDA), an illegal psychoactive drug reported to have enactogenic and stimulant properties. Piperonal is also used in the synthesis of tadalafil.

Fragrance

Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry. For this reason it commonly used in fragrances and artificial 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). Perfumers began to use the fragrance for the first time by the early 1880s. It is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent's character.