Isosafrole

Isosafrole is an organic compound that is used in the fragrance industry. Structurally, the molecule is related to allylbenzene, 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
Ball-and-stick model of isosafrole
Names
Preferred IUPAC name
5-(Prop-1-enyl)-2H-1,3-benzodioxole
Other names
5-(1-Propenyl)-1,3-benzodioxole
3,4-Methylenedioxyphenyl-1-propene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.010
EC Number
  • 204-410-2
  • (cis): 241-611-4
KEGG
RTECS number
  • (trans): DA5950000
UNII
UN number 3082
  • InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3
    Key: VHVOLFRBFDOUSH-UHFFFAOYSA-N
  • (trans): InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+ checkY
    Key: VHVOLFRBFDOUSH-NSCUHMNNSA-N checkY
  • (cis): InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2-
    Key: VHVOLFRBFDOUSH-IHWYPQMZSA-N
  • CC=Cc1ccc2OCOc2c1
  • (trans): C/C=C/C1=CC2=C(C=C1)OCO2
  • (cis): C/C=C\C1=CC2=C(C=C1)OCO2
Properties
C10H10O2
Molar mass 162.188 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 255 °C (491 °F; 528 K) trans
243 °C, cis
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Danger
H302, H315, H341, H350
P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P405, P501
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Isosafrole is a precursor to the important fragrance piperonal.[3] 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. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. 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
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