Isosafrole

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Isosafrole[1]
Isosafrole.png
trans-Isosafrole
Isosafrole.svg
cis-Isosafrole
Ball-and-stick model of isosafrole
Identifiers
CAS number 120-58-1 N, 4043-71-4 (trans), 17627-76-8 (cis)
ChemSpider 21106329 YesY
ChEMBL CHEMBL487603 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H10O2
Molar mass 162.19 g mol−1
Density 1.1206 g/cm3, trans
1.1182 g/cm3, cis
Melting point 8.2 °C (46.8 °F; 281.3 K) trans
-21.5 °C, cis
Boiling point 253 °C (487 °F; 526 K) trans
77–79 °C, cis @ 3.5 mmHg
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

Isosafrole is an organic compound that is used in the fragrance industry. Structurally, the molecule is related to phenylpropene, a type of aromatic organic chemical. Its fragrance is 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 via the intermediate compound MDP2P into the psychoactive drug MDMA ('ecstasy'). As such it requires permits to purchase or sell in any significant quantity in the US.

References[edit]

  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, Wiley-VCH, Weinheim, 2003. doi:10.1002/14356007.a11_141