safrole
Also known as safrol, shikimole, shikimol, 3-(3,4-methylenedioxyphenyl)prop-1-ene, allylcatechol methylene ether, 5-allyl-benzo[1,3]dioxole, m-allylpyrocatechin methylene ether, 4-allyl-1,2-methylenedioxybenzene
Safrole is a possibly-carcinogenic, organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.
Chemical data
- Formula
- C10H10O2
- Molecular weight
- 162.18 g/mol
- IUPAC name
- 5-prop-2-enyl-1,3-benzodioxole
- SMILES
- C=CCC1=CC2=C(C=C1)OCO2
- InChIKey
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 18.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
916 papers~12 min read
Article
12 sectionsContents
- History
- Natural occurrence
- Applications
- Synthesis
- Isosafrole
- Metabolism
- Toxicity
- Adverse effects
- Use in MDMA manufacture
- See also
- References
- External links
Safrole is a possibly-carcinogenic, organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.
It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide, the fragrance piperonal via isosafrole, and the empathogenic/entactogenic substance MDMA.