Names | |
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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 | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.935 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H12O | |
Molar mass | 148.20 g/mol |
Density | 0.946 g/cm3 |
Boiling point | 216 °C (421 °F; 489 K) 95–96 °C (203–205 °F; 368–369 K) at 12 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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 an allyl 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. [1]
The compound is named for estragon, the French name of tarragon.
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%). It is also present in pine oil, turpentine, fennel, anise (2% [2] ), frankincense (4% [3] ), Clausena anisata , and Syzygium anisatum .
Estragole is used in perfumes and in flavorings for foods. In the European Union, it can only be present in a flavor by using an essential oil. [4] Upon treatment with potassium hydroxide, estragole converts to anethole. [1] Estragole is used in the synthesis of magnolol.[ citation needed ]
Estragole is suspected to be carcinogenic and genotoxic, as is indicated by a report of the European Union Committee on Herbal Medicinal Products. [5] 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 (that is, these events are not linear with respect to dose).[ citation needed ] 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 to 1,000 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. [5]
The Scientific Committee on Food from the Health and Consumer Protection Directorate 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." [6]
Tarragon, also known as estragon, is a species of perennial herb in the family Asteraceae. It is widespread in the wild across much of Eurasia and North America and is cultivated for culinary and medicinal purposes.
Anise, also called aniseed or rarely anix, is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and Southwest Asia.
Fennel is a flowering plant species in the carrot family. It is a hardy, perennial herb with yellow flowers and feathery leaves. It is indigenous to the shores of the Mediterranean but has become widely naturalized in many parts of the world, especially on dry soils near the sea coast and on riverbanks.
An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is essential in the sense that it contains the essence of the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term "essential" used here does not mean indispensable or usable by the human body, as with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism.
Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.
Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.
Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent. A colorless oil, linalool is classified as an acyclic monoterpenoid. In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate.
Dysphania ambrosioides, formerly Chenopodium ambrosioides, known as epazote, Jesuit's tea, Mexican tea or wormseed, is an annual or short-lived perennial herb native to the Americas.
Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of the aromatic compound allylbenzene and occurs widely in the essential oils of plants. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; this is called the ouzo effect.
Peumus boldus, commonly known as boldo, is a species of tree in the family Monimiaceae and the only species in the genus Peumus. It is endemic to the central region of Chile, between 33° and 40° southern latitude. Boldo has also been introduced to Europe and North Africa, though it is not often seen outside botanical gardens.
Apiole is a phenylpropene, also known as apiol, parsley apiol, or parsley camphor. Its chemical name is 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. It is found in the essential oils of celery leaf and all parts of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation.
Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as Myroxylon balsamum var. pereirae; it is found in El Salvador, where it is an endemic species.
Syzygium anisatum, with common names ringwood and aniseed tree, is a rare Australian rainforest tree with an aromatic leaf that has an essential oil profile comparable to true aniseed.
Tagetes lucida is a perennial plant native to Mexico and Central America. It is used as a medicinal plant and as a culinary herb. The leaves have a tarragon-like scent, with hints of anise, and it has entered the nursery trade in North America as a tarragon substitute. Common names include sweetscented marigold, Mexican marigold, Mexican mint marigold, Mexican tarragon, sweet mace, Texas tarragon, pericón, yerbaniz, and hierbanís.
Dianethole is a naturally occurring organic compound that is found in anise and fennel. It is a dimeric polymer of anethole. It has estrogenic activity, and along with anethole and photoanethole, may be responsible for the estrogenic effects of anise and fennel. These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, which may explain their estrogenic activity. In fact, it is said that diethylstilbestrol and related drugs were originally modeled after dianethole and photoanethole.
The history of spices reach back thousands of years, dating back to the 8th century B.C. Spices are widely known to be developed and discovered in Asian civilizations. Spices have been used in a variety of antique developments for their unique qualities. There were a variety of spices that were used for common purposes across the ancient world. Different spices hold a value that can create a variety of products designed to enhance or suppress certain taste and/or sensations. Spices were also associated with certain rituals to perpetuate a superstition or fulfill a religious obligation, among other things.
Photoanethole is a naturally occurring organic compound that is found in anise and fennel. It has estrogenic activity, and along with anethole and dianethole, may be responsible for the estrogenic effects of anise and fennel. These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, which may explain their estrogenic activity. In fact, it is said that diethylstilbestrol and related drugs were originally modeled after photoanethole and dianethole.
Greek basil is a flowering herb and cultivar of basil.