Estragole

Estragole
IUPAC name 1-allyl-4-methoxybenzene
Other names 1-methoxy-4-(2-propenyl)-benzene; estragol; estragon; p-allylanisole; chavicyl methylether; methylchavicol; chavicol methylether; isoanethole.
Identifiers
CAS number	140-67-0 Y
ChemSpider	13850247 Y
UNII	9NIW07V3ET Y
KEGG	C10452 Y
ChEMBL	CHEMBL470671 Y
Jmol-3D images	Image 1
SMILES COc1ccc(CC=C)cc1
InChI InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 Y Key: ZFMSMUAANRJZFM-UHFFFAOYSA-N Y InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 Key: ZFMSMUAANRJZFM-UHFFFAOYAS
Properties
Molecular formula	C10H12O
Molar mass	148.20 g/mol
Density	0.946 g/cm3
Boiling point	216 °C; 95-96 °C at 12 mmHg
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Estragole (p-allylanisole, methyl chavicol) is a phenylpropene, a natural organic compound. Its chemical structure consists of a benzene ring substituted with a methoxy group and a propenyl group. Estragole is a double-bond isomer of anethole. It is a colorless to pale yellow liquid. It is the primary constituent of essential oil of tarragon, making up 60–75% of the oil. It is also found in essential oils of basil (23–88%), pine oil, turpentine, fennel, anise (2%^[1]), and Syzygium anisatum.

Estragole is used in perfumes and as a food additive for flavor. It is described in the flavors trade as "strong, sweet, tarragon"^{[citation needed]}.

Risks

Estragole is suspected to be carcinogenic and genotoxic, as is indicated by a report of the European Union, Committee on Herbal Medicinal Products.^[2] Several studies have clearly established that the profiles of metabolism, metabolic activation, and covalent binding are dose dependent and that the relative importance diminishes markedly at low levels of exposure (i.e. these events are not linear with respect to dose). In particular, rodent studies show that these events are minimal probably in the dose range of 1–10 mg/kg body weight, which is approximately 100-1000 times the anticipated human exposure to this substance. For these reasons it is concluded that the present exposure to estragole resulting from consumption of herbal medicinal products (short time use in adults at recommended posology) does not pose a significant cancer risk. In the meantime exposure of estragole to sensitive groups such as young children, pregnant and breastfeeding women should be minimized. The Scientific Committee on Food from the Health & Consumer Protection Directorate-General took a more concerned position and concluded that "Estragole has been demonstrated to be genotoxic and carcinogenic. Therefore the existence of a threshold cannot be assumed and the Committee could not establish a safe exposure limit. Consequently, reductions in exposure and restrictions in use levels are indicated.^[3]

See also

• Anethole, a double bond isomer
• Chavicol, the phenol analog
• Safrole, a methylenedioxy analog
• Vaporizer

References

1. ^ Philip R. Ashurst (1999). chavicol Food Flavorings. Springer. p. 11. http://books.google.com/books?id=hrWuqmtwJiEC&pg=PA18&dq=methyl chavicol. 
2. ^ EMEA/HMPC/137212/2005, Committee on Herbal Medicinal Products. Final Public Statement on the Use of Herbal Medicinal Products Containing Estragole http://www.ema.europa.eu/pdfs/human/hmpc/13721205en.pdf
3. ^ SCF/CS/FLAV/FLAVOUR/6, 26 September 2001, Opinion of the Scientific Committee on Food on Estragole (1-Allyl-4-methoxybenzene)http://ec.europa.eu/food/fs/sc/scf/out104_en.pdf

External links

• Opinion by the Scientific Committee on Food of the European Union on Estragole