Estragole
Encyclopedia
Estragole 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%), 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" .
, 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.
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.
Phenylpropene
Phenylpropenes, propenylphenols or allylbenzenes are a class of phenylpropanoids, a type of polyphenols.The phenylpropenes, including eugenol, chavicol, safrole and estragole, are derived from the monolignols. These compounds are the primary constituents of various essential oils....
, a natural organic compound. Its chemical structure consists of a benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
ring substituted with a methoxy group and a propenyl group. Estragole is a double-bond isomer of anethole
Anethole
Anethole is a phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils...
. It is a colorless to pale yellow liquid. It is the primary constituent of essential oil
Essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
of tarragon
Tarragon
Tarragon or dragon's-wort is a perennial herb in the family Asteraceae related to wormwood. Corresponding to its species name, a common term for the plant is "dragon herb". It is native to a wide area of the Northern Hemisphere from easternmost Europe across central and eastern Asia to India,...
, making up 60–75% of the oil. It is also found in essential oils of basil
Basil
Basil, or Sweet Basil, is a common name for the culinary herb Ocimum basilicum , of the family Lamiaceae , sometimes known as Saint Joseph's Wort in some English-speaking countries....
(23–88%), pine oil
Pine oil
Pine oil is an essential oil obtained by the steam distillation of needles, twigs and cones from a variety of species of pine, particularly Pinus sylvestris....
, turpentine
Turpentine
Turpentine is a fluid obtained by the distillation of resin obtained from trees, mainly pine trees. It is composed of terpenes, mainly the monoterpenes alpha-pinene and beta-pinene...
, fennel
Fennel
Fennel is a plant species in the genus Foeniculum . It is a member of the family Apiaceae . It is a hardy, perennial, umbelliferous herb, with yellow flowers and feathery leaves...
, anise
Anise
Anise , Pimpinella anisum, also called aniseed, is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and Southwest Asia. Its flavor resembles that of liquorice, fennel, and tarragon.- Biology :...
(2%), 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" .
Risks
Estragole is suspected to be carcinogenic and genotoxicGenotoxic
In genetics, genotoxicity describes a deleterious action on a cell's genetic material affecting its integrity. This includes both certain chemical compounds and certain types of radiation....
, 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.
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.
See also
- AnetholeAnetholeAnethole is a phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils...
, a double bond isomer - ChavicolChavicolChavicol, or p-allylphenol, is a natural phenylpropene, a type of organic compound. Its chemical structure consists of a benzene ring substituted with a hydroxy group and a propenyl group. It is a colorless liquid found together with terpenes in betel oil. It is miscible with alcohol, ether, and...
, the phenol analog - SafroleSafroleSafrole, 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 , or synthesized from other related methylenedioxy...
, a methylenedioxy analog - VaporizerVaporizerA vaporizer or vapouriser is a device used to extract for inhalation the active ingredients of plant material, commonly cannabis, tobacco, or other herbs or blends....