Isosafrole

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[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 (trans): 4043-71-4^N (cis): 17627-76-8^N
3D model (JSmol)	Interactive image (trans): Interactive image (cis): Interactive image
ChEBI	CHEBI:6054
ChEMBL	ChEMBL487603^Y
ChemSpider	(trans): 21106329^Y (cis): 1266029
ECHA InfoCard	100.004.010
EC Number	204-410-2 (cis): 241-611-4
KEGG	C10472
PubChem CID	(trans): 637796 (cis): 1549044
RTECS number	(trans): DA5950000
UNII	(trans): 94BY31ALL6 (cis): 253QUA24R1
UN number	3082
CompTox Dashboard (EPA)	DTXSID2020767
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 (trans): C/C=C/C1=CC2=C(C=C1)OCO2 (cis): C/C=C\C1=CC2=C(C=C1)OCO2
Properties
Chemical formula	C10H10O2
Molar mass	162.188 g·mol^−1
Density	1.1206 g/cm^3, trans 1.1182 g/cm^3, cis
Melting point	8.2 °C (46.8 °F; 281.3 K) trans -21.5 °C, cis
Boiling point	255 °C (491 °F; 528 K) trans 243 °C, cis
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H315, H341, H350
GHS precautionary statements	P201, P202, P264, P270, P280, P281, P301+312, P302+352, P308+313, P321, P330, P332+313, P362, P405, P501
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 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