safrole

Safrole[1]
IUPAC name	5-(2-Propenyl)-1,3-benzodioxole
Other names	Shikimol 5-Allylbenzo[d][1,3]dioxole
Identifiers
CAS number	[94-59-7]
SMILES	C=CCC1=CC=C(OCO2)C2=C1
Properties
Molecular formula	C10H10O2
Molar mass	162.19 g/mol
Density	1.096 g/cm3
Melting point	11 °C
Boiling point	232-234 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox 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, where it functions as a natural pesticide. The Ocotea cymbarum^{[verification needed]} oil made of the Ocotea pretiosa^{[verification needed]},^[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.

It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide.

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 basil, cinnamon, nutmeg, and pepper. 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 and tomatoes.^[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, it was shown that 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 MDMA manufacture, 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 as the yield is low and the effort required to get useful amounts of material is great. 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. 
4. ^ T. Y. Liu (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. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T6P-3X9415Y-3&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=8ec1ea8630ab130def74241535d2fc11. 
5. ^ "Ranking Possible Cancer Hazards on the HERP Index". http://potency.lbl.gov/pdfs/herp.pdf. Retrieved on 2007-03-19. 
6. ^ http://www.ncbi.nlm.nih.gov/pubmed/14422,"Absorption, metabolism and excretion of safrole in the rat and man.",Toxicology,1977 Feb;7(1):69-83,Benedetti MS, Malnoë A, Broillet AL.
7. ^ http://drugs.homeoffice.gov.uk/publication-search/drug-licences/ecfeb04?view=Binary 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

External links

• EU Narcotic drugs and psychotropic substances: internal aspects