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Safrole
From Wikipedia, the free encyclopedia
| Safrole[1] | |
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| Chemical name | 5-(2-Propenyl)-1,3-benzodioxole |
| Other names | Shikimol 5-Allylbenzo[d][1,3]dioxole |
| Chemical formula | C10H10O2 |
| Molecular mass | 162.188 g/mol |
| CAS number | 94-59-7 |
| Density | 1.096 g/cm3 |
| Melting point | 11 °C |
| Boiling point | 232-234 °C |
| SMILES | C=CCC1=CC=C(OCO2)C2=C1 |
| Disclaimer and references | |
Safrole is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants. It has a characteristic "candy-shop" aroma.
Safrole was once widely used as a food additive in root beer, sassafras tea, and other common goods. However, the Food and Drug Administration (FDA) barred the use of safrole after it was shown to be mildly carcinogenic. Today, safrole is also banned for use in soap and perfumes by IFRA.
It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide. More recently, safrole has been used as the main precursor for the clandestine manufacture of MDMA (Ecstasy) and MDEA (Eve). The standard synthetic procedure for the production of MDMA from safrole is via isomerization in the presence of a strong base to isosafrole. This is then oxidised to 3,4-methylenedioxy phenyl-2-propanone. Finally a reductive amination with either methylamine (to make MDMA) or ethylamine (to make MDEA). A newer synthesis method makes use of the Wacker process (palladium(II) chloride catalyst and 1,4-benzoquinone) to oxidize safrole directly to the 3,4-methylenedioxy phenyl-2-propanone intermediate.
It is nearly impossible to obtain large quantities of safrole and/or sassafras oil without arousing the suspicion of law enforcement, as Safrole is currently a List I chemical. Moreover, safrole is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[2]
- ^ Merck Index, 11th Edition, 8287.
- ^ International Narcotics Control Board