Piperonal

Piperonal
IUPAC name

1,3-Benzodioxole-5-carbaldehyde
Other names

Heliotropin; Heliotropine; Piperonyl aldehyde; Protocatechuic aldehyde methylene ether; 3,4-methylenedioxybenzaldehyde;
Identifiers
CAS number 120-57-0 Y
ChemSpider 13859497 N
UNII KE109YAK00 Y
ChEMBL CHEMBL271663 N
Jmol-3D images Image 1
Image 2
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]
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[2]

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.[3]

References

  1. ^ a b c d e Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123 
  2. ^ Heliotropin, Polarized Light Microscopy Digital Image Gallery
  3. ^ PiHKAL

External links

 Chisholm, Hugh, ed (1911). "Piperonal". Encyclopædia Britannica (11th ed.). Cambridge University Press.