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Piperonal
Encyclopedia
Piperonal, also known as heliotropin, is an aromatic aldehyde
that comes as transparent crystals, C8H6O3, and has a floral odor commonly described as being similar to that of vanillin
and cherry
. It is used as flavoring and in perfume
. It can be obtained by oxidation of piperonyl alcohol or the reduction of piperic acid
. It is also a minor natural component of the extract of vanilla
. It is a common additive in inexpensive synthetic vanilla flavor and candies.
Piperonal has powerful aromatherapeutic
qualities that appear to elevate mood and general well-being. Tests performed by the Memorial Sloan-Kettering Cancer Center in New York demonstrated a reduction in the anxiety of patients receiving an MRI
by as much as 63 percent.
(MDA). In one synthetic path, nitroethane
in a glacial acetic acid solution with an ammonium acetate
catalyst yields a substituted nitrostyrene via a condensation reaction
. This intermediate can then be reduced by a strong reducing agent such as lithium aluminium hydride
(LiAlH4) to yield MDA.
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
that comes as transparent crystals, C8H6O3, and has a floral odor commonly described as being similar to that of vanillin
Vanillin
Vanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. It is also found in Leptotes bicolor, roasted coffee and the Chinese red pine...
and cherry
Cherry
The cherry is the fruit of many plants of the genus Prunus, and is a fleshy stone fruit. The cherry fruits of commerce are usually obtained from a limited number of species, including especially cultivars of the wild cherry, Prunus avium....
. It is used as flavoring and in perfume
Perfume
Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...
. It can be obtained by oxidation of piperonyl alcohol or the reduction of piperic acid
Piperic acid
Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine from black pepper, followed by acidification of the corresponding salt...
. It is also a minor natural component of the extract of vanilla
Vanilla
Vanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...
. It is a common additive in inexpensive synthetic vanilla flavor and candies.
Piperonal has powerful aromatherapeutic
Aromatherapy
Aromatherapy is a form of alternative medicine that uses volatile plant materials, known as essential oils, and other aromatic compounds for the purpose of altering a person's mind, mood, cognitive function or health....
qualities that appear to elevate mood and general well-being. Tests performed by the Memorial Sloan-Kettering Cancer Center in New York demonstrated a reduction in the anxiety of patients receiving an MRI
Magnetic resonance imaging
Magnetic resonance imaging , nuclear magnetic resonance imaging , or magnetic resonance tomography is a medical imaging technique used in radiology to visualize detailed internal structures...
by as much as 63 percent.
Chemistry
Piperonal may be used in the synthesis of 3,4-methylenedioxyamphetamine3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
(MDA). In one synthetic path, nitroethane
Nitroethane
Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colourless and has a fruity odor.- Preparation :...
in a glacial acetic acid solution with an ammonium acetate
Ammonium acetate
Ammonium acetate is a chemical compound with the formula CH3COONH4 . It is a white solid, which can be derived from the reaction of ammonia and acetic acid...
catalyst yields a substituted nitrostyrene via a condensation reaction
Condensation reaction
A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride,...
. This intermediate can then be reduced by a strong reducing agent such as lithium aluminium hydride
Lithium aluminium hydride
Lithium aluminium hydride, commonly abbreviated to LAH or known as LithAl, is an inorganic compound with the chemical formula LiAlH4. It was discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters,...
(LiAlH4) to yield MDA.