Safrole
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| Names | |
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IUPAC name
5-(Prop-2-en-1-yl)-2H-1,3-benzodioxole
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| Other names
5-(2-Propenyl)-1,3-benzodioxole
5-Allylbenzo[d][1,3]dioxole 3,4-Methylenedioxyphenyl-2-propene |
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.133 |
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| Properties | |
| C10H10O2 | |
| Molar mass | 162.19 g/mol |
| Density | 1.096 g/cm3 |
| Melting point | 11 °C (52 °F; 284 K) |
| Boiling point | 232 to 234 °C (450 to 453 °F; 505 to 507 K) |
| -97.5·10−6 cm3/mol | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Safrole 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 is synthesized from catechol or 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, a plant growing in Brazil, and sassafras oil made from Sassafras albidum, 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, the fragrance piperonal via isosafrole, and the empathogenic/entactogenic drug MDMA.
Studies in the 1960s suggested that safrole was carcinogenic, causing permanent liver damage in animals. Consequently, the US Food and Drug Administration (FDA) banned sassafras and safrole for human consumption.
Safrole is still regarded by FDA to be a weak carcinogen in rats. However, 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. The European Commission on Health and consumer protection assumes safrole to be genotoxic and carcinogenic. 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. 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.
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Wikipedia