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| Names | |
|---|---|
| IUPAC name 1,3-benzodioxole-5-carbaldehyde | |
| Other names heliotropine, protocatechuic aldehyde methylene ether | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.004.009 
|
| UNII | |
| CompTox Dashboard (EPA) | |
SMILES
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| Properties | |
| Chemical formula | C8H6O3 |
| Molar mass | 150.13 g/mol |
| Melting point | 35-37 °C |
| Boiling point | 264 °C (507 °F; 537 K) |
| Solubility in THF, ethanol, methanol | THF 7.44 M, ethanol 4.99 M, methanol 7.29 M |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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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 which 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.
Chemistry
Piperonal may be used in the synthesis of 3,4-methylenedioxyamphetamine (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.
References
- Solubility of piperonal in non-aqueous solvents
- Heliotropin, Polarized Light Microscopy Digital Image Gallery
- PiHKAL
External links
Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press. {{cite encyclopedia}}: Missing or empty |title= (help)