Isosafrole

Isosafrole

Isosafrole[1]

trans-Isosafrole

cis-Isosafrole
Ball-and-stick model of isosafrole
Names
IUPAC name
5-(Prop-1-enyl)benzo[d][1,3]dioxole
Other names
5-(1-Propenyl)-1,3-benzodioxole
3,4-Methylenedioxyphenyl-1-propene
Identifiers
 N
(trans) N
(cis) N
ChEMBL  YesY
ChemSpider  YesY
Jmol-3D images Image
Properties
small=yes}}} }}} 0}}} 1=C|C} }}} 1=H|H} }}} 1=Ac|Ac} }}} 1=Ag|Ag} }}} 1=Al|Al} }}} 1=Am|Am} }}} 1=Ar|Ar} }}} 1=As|As} }}} 1=At|At} }}} 1=Au|Au} }}} 1=B|B} }}} 1=Ba|Ba} }}} 1=Be|Be} }}} 1=Bh|Bh} }}} 1=Bi|Bi} }}} 1=Bk|Bk} }}} 1=Br|Br} }}} 1=Ca|Ca} }}} 1=Cd|Cd} }}} 1=Ce|Ce} }}} 1=Cf|Cf} }}} 1=Cn|Cn} }}} 1=Cl|Cl} }}} 1=Cm|Cm} }}} 1=Co|Co} }}} 1=Cr|Cr} }}} 1=Cs|Cs} }}} 1=Cu|Cu} }}} 1=Db|Db} }}} 1=Ds|Ds} }}} 1=Dy|Dy} }}} 1=Er|Er} }}} 1=Es|Es} }}} 1=Eu|Eu} }}} 1=F|F} }}} 1=Fe|Fe} }}} 1=Fl|Fl} }}} 1=Fm|Fm} }}} 1=Fr|Fr} }}} 1=Ga|Ga} }}} 1=Gd|Gd} }}} 1=Ge|Ge} }}} 1=He|He} }}O2}}
Documentation

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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

Isosafrole is an 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

  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