Piperonal

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Piperonal

IUPAC name[hide] 1,3-Benzodioxole-5-carbaldehyde Other names[hide] Heliotropin; Heliotropine; Piperonyl aldehyde; Protocatechuic aldehyde methylene ether; 3,4-methylenedioxybenzaldehyde; Identifiers CAS number 120-57-0 ChemSpider 13859497 UNII KE109YAK00 ChEMBL CHEMBL271663 Image 1 Jmol-3D images Image 2 SMILES [show] InChI [show] Properties Molecular formula C8H6O3 Molar mass 150.13 g mol1 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) 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]

Contents

1 Preparation and reactions 2 Fragrance 3 References 4 External links

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 wellbeing. 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
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 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, WileyVCH, Weinheim, 2003. doi:10.1002/14356007.a11_141 3. ^ http://www.erowid.org/library/books_online/pihkal/pihkal.shtml PiHKAL] 4. ^ Heliotropin, Polarized Light Microscopy Digital Image Gallery

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

Isosafrole
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Isosafrole[1]

IUPAC name[hide] (E)-5-(prop-1-enyl)benzo[d][1,3]dioxole Other names[hide] 5-(1-propenyl)-1,3-benzodioxole; 3,4-methylenedioxyphenyl-1-propene Identifiers 120-58-1 , CAS number [4043-71-4] (trans) [17627-76-8] (cis) ChemSpider 21106329 ChEMBL CHEMBL487603 Jmol-3D images Image 1 SMILES [show] InChI [show] Properties Molecular formula C10H10O2 Molar mass 162.188 g/mol 1.1206 g/cm3, trans Density 1.1182 g/cm3, cis 8.2 C, trans Melting point -21.5 C, cis 253 C, trans Boiling point 7779 C, cis @ 3.5 mmHg (verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

Isosafrole is an organic compound that is used in fragrance industry. Structurally, the molecule is related to phenylpropene, a type of aromatic organic chemical. Its fragrance reminiscent of anise or licorice. It is found in small amounts in various essential oils, but is most commonly obtained by isomerizing the plant oil safrole. It exists as two geometric isomers, cis-isosafrole and trans-isosafrole. Isosafrole is a precursor to the important fragrance piperonal.[2] It can also be converted to the illegal drug MDP2P which is converted into the psychoactive drug MDMA ('ecstasy'). As such requires permits to purchase or sell in any significant quantity in the US.

References
1. ^ Merck Index, 11th Edition, 5112. 2. ^ 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, WileyVCH, Weinheim, 2003. doi:10.1002/14356007.a11_141

Piperic acid
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Piperic acid

IUPAC name[hide]
5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid

CAS number ChEMBL Jmol-3D images

Identifiers 136-72-1 CHEMBL332122 Image 1 SMILES

[show]
Molecular formula Molar mass Boiling point Properties C12H10O4 218.21 g mol1 decomposes (verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine[1] from black pepper[2], followed by acidification of the corresponding salt.[3] Piperic acid is an intermediate in the synthesis of other compounds such as piperonal, and as-such may be used to produce fragrances, perfumes flavorants and drugs as well as other useful compounds.

Contents

1 Preparation 2 Reactions 3 See also 4 References

Preparation
Piperic acid can be prepared from the commercially-available alkaloid piperine, a cyclic amide containing a piperidine group, by reacting it with a hydroxide such as potassium hydroxide, then acidifying the formed piperate salt with hydrochloric acid or another acid. The toxic compound piperidine is given off during the base-hydrolysis of piperine and as-such, safety precautions should be taken.

Reactions
Reaction of piperic acid with strong oxidizers such as potassium permanganate or ozone, or a halogen such as bromine followed by sodium hydroxide causes the oxidative cleavage of the double-bonds, yielding piperonal via ozonolysis[4][5]. Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals.

See also

Piperonal Piperine Safrole Isosafrole Sesamol Piperonyl butoxide

Cinnamic acid

References
1. ^ Paul M. Dewick. (2009). Medicinal natural products : a biosynthetic approach. Chichester: A John Wiley & Sons. p. 327. ISBN 978-0-470-74167-2. 2. ^ http://chestofbooks.com/health/aromatherapy/The-Volatile-Oils-Vol1/Heliotropin.html 3. ^ http://www.erowid.org/archive/rhodium/chemistry/3base/piperonal.pepper/degradation.pi perine/index.html 4. ^ http://www.freepatentsonline.com/5095128.html, Preparation process for piperonal, US Patent No. 5095128 5. ^ http://www.erowid.org/archive/rhodium/chemistry/3base/piperonal.pepper/cleavage.piper ic_acid/index.html