Safrol

Safrole[1]
Identifiers
CAS number 94-59-7 YesY
ChemSpider 13848731 YesY
KEGG C10490 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H10O2
Molar mass 162.19 g/mol
Density 1.096 g/cm3
Melting point

11 °C, 284 K, 52 °F

Boiling point

232–234 °C

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Safrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil (although commercially available culinary sassafras oil is usually devoid of safrole due to a rule passed by the FDA in 1960), 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, where it functions as a natural pesticide. Ocotea cymbarum oil made from Ocotea pretiosa,[2] a plant growing in Brazil, and sassafras oil made from Sassafras albidum,[3] a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "sweet-shop" aroma.

It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the empathogenic/entactogenic drug MDMA.

Carcinogenicity

Safrole is regarded by the US Food and Drug Administration (FDA) to be a weak carcinogen in rats,[4] and considered by the European Commission on Health and consumer protection to be genotoxic and carcinogenic.[5] It occurs naturally in a variety of spices, such as cinnamon, nutmeg, and black pepper and herbs such as basil. In that role, safrole, like many naturally occurring compounds, may have a small but measurable ability to induce cancer in rodents. Despite this, the effects in humans were estimated by the Lawrence Berkeley National Laboratory to be similar to risks posed by breathing indoor air or drinking municipally supplied water.[6] In the United States, it was once widely used as a food additive in root beer, sassafras tea, and other common goods, but was banned by the FDA after its carcinogenicity in rats was discovered. Today, safrole is also banned for use in soap and perfumes by the International Fragrance Association.

According to a 1977 study of the metabolites of safrole in both rats and humans, two carcinogenic metabolites of safrole found in the urine of rats, 1'-hydroxysafrole and 3'-hydroxyisosafrole, were not found in human urine.[7]

Use in MDMA manufacture

Safrole is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[8] Due to its role in the manufacture of MDMA, safrole and isosafrole, as well as piperonal, are Category I precursors under regulation No 273/2004 of the European Community.[9] In the United States, safrole is currently a List I chemical.

The root bark of American sassafras contains a low percentage of steam-volatile oil, which is typically 75% safrole.[10] Attempts to refine safrole from sassafras bark are generally not economically viable due to low yield and high effort. Demand for safrole is causing rapid and illicit harvesting of the Cinnamomum parthenoxylon tree in Southeast Asia, in particular the Cardamom Mountains in Cambodia.[11] However, it is not clear what proportion of illicitly harvested safrole is going toward MDMA production, as over 90% of the global safrole supply (about 2000 metric tons per year) is used to manufacture pesticides, fragrances, and other chemicals.[12][13] Sustainable harvesting of safrole is possible from leaves and stems of certain plants.[12][13]

References

External links

  • EU Narcotic drugs and psychotropic substances: internal aspects

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