Isosafrole

Isosafrole^[1]

trans-Isosafrole
cis-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
CAS Number	120-58-1 N 4043-71-4 (trans) N 17627-76-8 (cis) N
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL487603 Y
ChemSpider	21106329 Y
ECHA InfoCard	100.004.010
InChI InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+ Y Key: VHVOLFRBFDOUSH-NSCUHMNNSA-N Y InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+ Key: VHVOLFRBFDOUSH-NSCUHMNNBU
SMILES CC=Cc1ccc2OCOc2c1
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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