Piperonal

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Piperonal
Piperonal structure.png
Identifiers
CAS number 120-57-0 YesY
ChemSpider 13859497 N
UNII KE109YAK00 YesY
ChEBI CHEBI:8240 N
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 (99 °F; 310 K)[1]
Boiling point 263 °C (505 °F; 536 K)[1]
Solubility in water Soluble in 500 parts[1]
Hazards
LD50 2700 mg/kg (orally in rats)[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.[2] The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.

Natural occurrence[edit]

Piperonal naturally occurs in various plants. Examples include dill, vanilla, violet flowers, and black pepper.

Preparation[edit]

Piperonal can be prepared by oxidizing isosafrole or by using a multistep sequence from catechol or 1,2-methylenedioxybenzene. Synthesis from the latter chemical is accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent.[2][3][4] Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane.[5]

Reactions[edit]

Piperonal, like all aldehydes, can be reduced to its alcohol (piperonyl alcohol) or oxidized to give its acid (piperonylic acid). Piperonal can be used to the synthesize 3,4-methylenedioxyamphetamine (MDA), an illict psychoactive drug reported to have enactogenic and stimulant properties.[6][7] Piperonal is also used in the synthesis of tadalafil.[8]

Fragrance[edit]

Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry. For this reason it commonly used in fragrances and artifical flavors.[2] The compound was named Heliotropin after the 'cherry pie' notes found in the heliotrope flower's fragrance (even though the chemical is not present in the flower's true aroma).[9] Perfumers began to use the fragrance for the first time by the early 1880s.[10] It is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent's character.[11]

References[edit]

  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. ^ a b c 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
  3. ^ Fatiadi, Alexander; and Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)". Journal of Research of the National Bureau of Standards - A. Physics and Chemistry 78A (3): 411–412. doi:10.6028/jres.078A.024. 
  4. ^ Nwaukwa, Stephen; Keehn, Philip (1982). "Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-hydroxy- and α-keto acids with calcium hypochlorite [Ca(OCl)2]". Tetrahedron Letters 23 (31): 3135–3138. doi:10.1016/S0040-4039(00)88578-0. 
  5. ^ Bonthrone, W. and Cornforth, J. (1969). "The methylenation of catechols". Journal of the Chemical Society: 1202–1204. doi:10.1039/J39690001202. 
  6. ^ Shulgin, Alexander; Manning, Tania; Daley, Paul (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (1st ed.). Berkeley, CA: Transform Press. p. 165. ISBN 9780963009630. 
  7. ^ Shulgin, Alexander; and Shulgin, Ann (1991). PiHKAL: A Chemical Love Story. Lafayette, CA: Transform Press. ISBN 9780963009609. 
  8. ^ Gilla, G.; Anumula, R.R.; Aalla, S.; Vurimidi, H.; and Ghanta, M.R. (2013). "Synthesis and characterization of related substances and metabolite of tadalafil, a PDE-5 inhibitor". Organic Communications 6 (1): 12–22. 
  9. ^ http://www.bojensen.net/EssentialOilsEng/EssentialOils13A/EssentialOils13A.htm
  10. ^ The Force of Fashion in Politics and Society: Global Perspectives from Early Modern to Contemporary Times By Beverly Lemire ISBN 9781409404927
  11. ^ The Good Scents Company database entry for Heliotropin

External links[edit]