Piperonal
| |
| Names | |
|---|---|
| IUPAC name
1,3-Benzodioxole-5-carbaldehyde
| |
| Other names
Heliotropin; Heliotropine; Piperonyl aldehyde; Protocatechuic aldehyde methylene ether; 3,4-methylenedioxybenzaldehyde;
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.009 |
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C8H6O3 | |
| Molar mass | 150.133 g·mol−1 |
| Appearance | Colorless crystals[1] |
| Density | 1.337 g/cm3 |
| Melting point | 37 °C (99 °F; 310 K) |
| Boiling point | 263 °C (505 °F; 536 K) |
| Soluble in 500 parts[1] | |
| Hazards | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
2700 mg/kg (orally in rats)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Piperonal, also known as heliotropin, is an organic compound that is commonly found in fragrances and flavors. The molecule is structurally related to benzaldehyde and vanillin. It exists as a white or colorless solid. It has a floral odor commonly described as being similar to that of vanillin and cherry. It is used as flavoring and in perfumes.[2]
Preparation and reactions
Piperonal is prepared by oxidation of isosafrole, which occurs naturally. It is also prepared in a multistep sequence from catechol or 1,2-methylenedioxybenzene by condensation with glyoxalic acid.[2]
Reduction gives piperonyl alcohol and oxidation gives piperic acid. Piperonal may be used in the synthesis of 3,4-methylenedioxyamphetamine (MDA) via the 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.[3]
Fragrance
It is 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.[4]
References
- ^ a b c d e Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- ^ a b 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. doi:10.1002/14356007.a11_141
- ^ http://www.erowid.org/library/books_online/pihkal/pihkal.shtml PiHKAL]
- ^ Heliotropin, Polarized Light Microscopy Digital Image Gallery
External links
Chisholm, Hugh, ed. (1911). . Encyclopædia Britannica (11th ed.). Cambridge University Press. {{cite encyclopedia}}: Unknown parameter |W1EC= ignored (help)