Structure via PubChem · Public domain (PubChem)
isosafrole
Sign in to saveAlso known as 5-prop-1-enyl-1,3-benzodioxole
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.
Chemical data
- Formula
- C10H10O2
- Molecular weight
- 162.18 g/mol
- IUPAC name
- 5-prop-1-enyl-1,3-benzodioxole
- SMILES
- CC=CC1=CC2=C(C=C1)OCO2
- InChIKey
- VHVOLFRBFDOUSH-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 18.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 162.06807956
Show 3 more facts
- Commons category
- Isosafrole
- canonical SMILES
- CC=CC1=CC2=C(C=C1)OCO2
- chemical formula
- C₁₀H₁₀O₂
via Wikidata · CC0
~1 min read
Article
1 sectionsContents
- 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. 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.