Isosafrole

Isosafrole^[1]
	; trans-Isosafrole
	; cis-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
CAS Number	120-58-1 ; (trans): 4043-71-4 ; (cis): 17627-76-8 ;
3D model (JSmol)	(trans): Interactive image; (cis): Interactive image;
ChEBI	CHEBI:6054;
ChEMBL	ChEMBL487603 ;
ChemSpider	8131; (trans): 21106329 ; (cis): 1266029;
ECHA InfoCard	100.004.010
EC Number	204-410-2; (cis): 241-611-4;
KEGG	(trans): C10472;
PubChem CID	8439; (trans): 637796; (cis): 1549044;
RTECS number	(trans): DA5950000;
UNII	W6337429LF ; (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 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+ Key: VHVOLFRBFDOUSH-NSCUHMNNSA-N ; (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;
	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/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:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H341, H350
Precautionary statements	P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P405, P501
Legal status	BR: Class D1 (Drug precursors);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

[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.

[Ullmann-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

[1]

[2]

[3]

Names
trans-Isosafrole
cis-Isosafrole

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
CAS Number	120-58-1^Y (trans): 4043-71-4^Y (cis): 17627-76-8^Y
3D model (JSmol)	(trans): Interactive image (cis): Interactive image
ChEBI	CHEBI:6054
ChEMBL	ChEMBL487603^Y
ChemSpider	8131 (trans): 21106329^Y (cis): 1266029
ECHA InfoCard	100.004.010
EC Number	204-410-2 (cis): 241-611-4
KEGG	(trans): C10472
PubChem CID	8439 (trans): 637796 (cis): 1549044
RTECS number	(trans): DA5950000
UNII	W6337429LF^Y (trans): 94BY31ALL6^Y (cis): 253QUA24R1^Y
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 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+^Y Key: VHVOLFRBFDOUSH-NSCUHMNNSA-N^Y (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
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/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:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H341, H350
Precautionary statements	P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P405, P501
Legal status	BR: Class D1 (Drug precursors)^[2]
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