Safrole

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Template:Chembox E number
Safrole[1]
IUPAC name 5-(2-Propenyl)-1,3-benzodioxole
Other names Shikimol<br\>5-Allylbenzo[d][1,3]dioxole
Identifiers
3D model (JSmol)
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Properties
C10H10O2
Molar mass 162.188 g/mol
Density 1.096 g/cm3
Melting point
Boiling point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox 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. The Octea cymbarum oil made of the Octea pretiosa,[2] a plant growing in brazil, and sassafras oil made of the Sassafras albidum,[3] a plant growing in eastern North America, are the main natural sources for safrole. 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. Safrole is used as the main precursor for the clandestine manufacture of MDMA (ecstasy). The standard synthetic procedure for the production of MDMA from safrole is via isomerization in the presence of a strong base to isosafrole, oxidization to 3,4-methylenedioxy phenyl-2-propanone, finally a reductive amination with either methylamine (to make MDMA) or ethylamine (to make MDEA) or ammonia (to make MDA). 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.[4]

References

  1. Merck Index, 11th Edition, 8287.
  2. Hickey M. J. (1948). "Investigation of the Chemical Constitution of Brazilian Sassafras Oil". Journal of Organic Chemistry. 13 (3): 443–446.
  3. Kamdem D. P., Gage, D. A. (1995). "Chemical Composition of Essential Oil from the Root Bark of Sassafras albidum". Journal of Organic Chemistry. 61 (6): 574–575. doi:10.1055/s-2006-959379.
  4. International Narcotics Control Board

External links

de:Safrol nl:Safrol



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