Piperonal, also known as heliotropin, is an
organic compound which is commonly found in fragrances and flavors.
[Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe and Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2003. ] The molecule is structurally related to other
aromatic aldehydes such as
benzaldehyde
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.
It is a colorless liquid with a characteristic almond-like odor. ...
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 the oxidative cleavage of
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
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
.
Reactions
Piperonal, like all
aldehydes, can be
reduced to its
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
(piperonyl alcohol) or oxidized to give its
acid
In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
(piperonylic acid).
Piperonal can be used in the synthesis of some pharmaceutical drugs including
tadalafil,
L-DOPA, and
atrasentan
Atrasentan is an experimental drug that is being studied for the treatment of various types of cancer, including non-small cell lung cancer. It is also being investigated as a therapy for diabetic kidney disease.
Atrasentan failed a phase 3 tria ...
.
Fragrance
Piperonal has a floral odor which is commonly described as being similar to that of vanillin or
cherry
A cherry is the fruit of many plants of the genus ''Prunus'', and is a fleshy drupe (stone fruit).
Commercial cherries are obtained from cultivars of several species, such as the sweet ''Prunus avium'' and the sour ''Prunus cerasus''. The nam ...
. For this reason it is commonly used in fragrances and
artificial flavors
A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gust ...
.
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.
[The Force of Fashion in Politics and Society]
Global Perspectives from Early Modern to Contemporary Times By Beverly Lemire It is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent's character.
Piperonyl acetate is a synthetic cherry flavoring.
Use in MDMA Manufacture
Due to their role in the manufacture of
MDMA, safrole,
isosafrole, and piperonal are Category I precursors under regulation no. 273/2004 of the
European Community.
References
External links
{{EB1911 poster, Piperonal
Benzaldehydes
Benzodioxoles