Piperonal
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Piperonal
| Piperonal | |
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1,3-Benzodioxole-5-carbaldehyde |
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Other names
Heliotropin; Heliotropine; Piperonyl aldehyde; Protocatechuic aldehyde methylene ether; 3,4-methylenedioxybenzaldehyde; |
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| Identifiers | |
| CAS number | 120-57-0  |
| ChemSpider | 13859497  |
| UNII | KE109YAK00 |
| ChEMBL | CHEMBL271663 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C8H6O3 |
| Molar mass | 150.13 g mol−1 |
| Appearance | Colorless crystals[1] |
| Density | 1.337 g/cm3 |
| Melting point |
37 °C, 310 K, 99 °F ([1]) |
| Boiling point |
263 °C, 536 K, 505 °F ([1]) |
| Solubility in water | Soluble in 500 parts[1] |
| Hazards | |
| LD50 | 2700 mg/kg (orally in rats)[1] |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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]
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Contents
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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). "Piperonal". Encyclopædia Britannica (11th ed.). Cambridge University Press.
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