Isosafrole
Appearance
![]() trans-Isosafrole
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![]() cis-Isosafrole
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Names | |
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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 | |
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3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.010 |
EC Number |
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KEGG |
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PubChem CID
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RTECS number |
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UNII |
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UN number | 3082 |
CompTox Dashboard (EPA)
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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: | |
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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).
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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 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
- ^ Merck Index, 11th Edition, 5112
- ^ 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.
- ^ 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