Safrole

Chembox new
Name = Safrole
Reference = ["Merck Index", 11th Edition, 8287.]
ImageFile = safrole-Line-Structure.png ImageSize = 200px
ImageFile1 =
ImageSize1 = 200px
IUPACName = 5-(2-Propenyl)-1,3-benzodioxole
OtherNames = Shikimol
5-Allylbenzo [d] [1,3] dioxole
Section1 = Chembox Identifiers
CASNo = {CAS|94-59-7}
SMILES = C=CCC1=CC=C(OCO2)C2=C1
Section2 = Chembox Properties
Formula = C₁₀H₁₀O₂
MolarMass = 162.188 g/mol
Density = 1.096 g/cm³
MeltingPt = 11 °C
BoilingPt = 232-234 °C

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 Octea cymbarumVerify source|date=April 2008 oil made of the Octea pretiosaVerify source|date=April 2008, [cite journal | author = Hickey M. J.| title = Investigation of the Chemical Constitution of Brazilian Sassafras Oil | journal = Journal of Organic Chemistry| pages =443–446| year = 1948|volume = 13|issue = 3| doi= ] a plant growing in Brazil, and sassafras oil made of the Sassafras albidum, [cite journal | author = Kamdem D. P., Gage, D. A.| title = Chemical Composition of Essential Oil from the Root Bark of Sassafras albidum | journal = Journal of Organic Chemistry| pages =574–575| year = 1995|volume = 61|issue = 6| doi=10.1055/s-2006-959379] 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 a weak carcinogen. [cite journal | author = T. Y. Liu | title = Safrole-induced Oxidative Damage in the Liver of Sprague–Dawley Rats | journal = Food and Chemical Toxicology | pages = 697–702 | year = 1999 | volume = 37 | issue = 7 | url = 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 | doi = 10.1016/S0278-6915(99)00055-1] It naturally occurs in a variety of spices, for example basil, cinnamon, nutmeg, and pepper. In that role safrole is believed to make a small but measurable contribution to the overall incidence of human cancer. [cite web | title = Ranking Possible Cancer Hazards on the HERP Index | url = http://potency.lbl.gov/pdfs/herp.pdf | accessdate = 2007-03-19] In the US, 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 was discovered. Today, safrole is also banned for use in soap and perfumes by IFRA.

Use in MDMA manufacture

Safrole is often used as the 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, oxidation 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 both safrole and isosafrole as well as piperonal are Category I precursors under regulation No 273/2004 of the European Community. [http://drugs.homeoffice.gov.uk/publication-search/drug-licences/ecfeb04?view=Binary Regulation (EC) No 273/2004 of the European Parliament.] 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. [ The Merck Index, 13th edition, Merck & Co, Inc, Whitehorse Station, NJ, copyright 2001. ] 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 under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. [ http://www.incb.org/pdf/e/list/red.pdf International Narcotics Control Board] ]

References

External links

* [http://europa.eu.int/scadplus/leg/en/lvb/l14003b.htm EU Narcotic drugs and psychotropic substances: internal aspects]