Isosafrole

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
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 ?)

Isosafrole is an

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

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. doi:10.1002/14356007.a11_141
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