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Safrole

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Safrole[1]
Names
IUPAC name
5-(2-propenyl)-1,3-benzodioxole
Other names
5-allylbenzo[d][1,3]dioxole; 3,4-methylenedioxyphenyl-2-propene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.133 Edit this at Wikidata
KEGG
  • InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2 checkY
    Key: ZMQAAUBTXCXRIC-UHFFFAOYSA-N checkY
  • InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
    Key: ZMQAAUBTXCXRIC-UHFFFAOYAD
  • C=CCc1ccc2OCOc2c1
Properties
C10H10O2
Molar mass 162.19 g/mol
Density 1.096 g/cm3
Melting point 11 °C (52 °F; 284 K)
Boiling point 232-234 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Safrole, also known as shikimol, is a phenylpropene. It 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 (although commercially available sassafras oil is usually devoid of safrole via a rule passed by the FDA in 1960, see here), 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 recreational drug MDMA ("Ecstasy.")

Carcinogenicity

Safrole is regarded by the U.S. government to be a weak carcinogen in rats.[4] It naturally occurs in a variety of spices such as cinnamon, nutmeg, black pepper and herbs such as basil. In that role safrole is believed, although not proven, to make a small but measurable contribution to the overall incidence of human cancer, equal to the hazards presented by orange juice (due to limonene) and tomatoes (caffeic acid).[5] 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 Food and Drug Administration (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. This brings to question the actual carcinogenicity of safrole in humans.[6]

Use in MDMA manufacture

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.[7] In the US, safrole is currently a List I chemical. The root bark of American sassafras contains a few percent of steam volatile oil which is typically 75% safrole.[8] Attempts to access safrole from this source are generally not successful because the yield is low and the effort required to get useful amounts of material is great.[citation needed] Safrole is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[9]

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. doi:10.1021/jo01161a020.
  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. PMID 8824955.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ T. Y. Liu; Chen, CC; Chen, CL; Chi, CW (1999). "Safrole-induced Oxidative Damage in the Liver of Sprague–Dawley Rats". Food and Chemical Toxicology. 37 (7): 697–702. doi:10.1016/S0278-6915(99)00055-1. PMID 10496370.
  5. ^ "Ranking Possible Cancer Hazards on the HERP Index" (PDF). Retrieved 2007-03-19.
  6. ^ Benedetti MS, Malnoë A, Broillet AL (1977). "Absorption, metabolism and excretion of safrole in the rat and man". Toxicology. 7 (1): 69–83. doi:10.1016/0300-483X(77)90039-7. PMID 14422.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Regulation (EC) No 273/2004 of the European Parliament
  8. ^ The Merck Index, 13th edition, Merck & Co, Inc, Whitehorse Station, NJ, copyright 2001.
  9. ^ International Narcotics Control Board