Estragole

Estragole
Names


Preferred IUPAC name 1-Methoxy-4-(prop-2-en-1-yl)benzene
Other names 1-Methoxy-4-(2-propenyl)-benzene 1-Allyl-4-methoxybenzene Estragol Estragon p-Allylanisole Chavicyl methylether Methylchavicol Chavicol methylether Isoanethole 4-Allylanisole
Identifiers
CAS Number	140-67-0^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL470671^Y
ChemSpider	13850247^Y
ECHA InfoCard	100.004.935
KEGG	C10452^Y
UNII	9NIW07V3ET^Y
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
SMILES COc1ccc(CC=C)cc1
Properties
Chemical formula	C₁₀H₁₂O
Molar mass	148.20 g/mol
Density	0.946 g/cm³
Boiling point	216 °C (421 °F; 489 K) (95–96 °C at 12 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
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. It is an isomer of anethole, differing with respect to the location of the double bond. It is a colorless liquid, although impure samples can appear yellow. It is a component of various trees and plants, including turpentine (pine oil), anise, fennel, bay, tarragon, and basil. It is used in the preparation of fragrances.

Hundreds of tonnes of basil oil are produced annually by steam distillation of Ocimum basilicum (common basil). This oil is mainly estragole but also contains substantial amounts of linalool. Estragole is the primary constituent of essential oil of tarragon (comprising 60–75%), pine oil, turpentine, fennel, anise (2%), Clausena anisata and Syzygium anisatum.

Estragole is used in perfumes and as a food additive for flavor. Upon treatment with potassium hydroxide, estragole converts to anethole.

Estragole is suspected to be carcinogenic and genotoxic, as is indicated by a report of the European Union, Committee on Herbal Medicinal Products. 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.

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Wikipedia