Estragole

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Estragole
Estragole acsv.svg
Estragole-3D-balls.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.935 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-427-8
KEGG
PubChem CID
UNII
  • InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 Yes check.svgY
    Key: ZFMSMUAANRJZFM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3
    Key: ZFMSMUAANRJZFM-UHFFFAOYAS
  • COc1ccc(CC=C)cc1
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

The compound is named for estragon, the French name of tarragon.

Production

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] ), Clausena anisata and Syzygium anisatum .

Estragole is used in perfumes and is restricted in flavours as a biologically active principle: it can only be present in a flavour by using an essential oil. [3] Upon treatment with potassium hydroxide, estragole converts to anethole. [1] A known use of estragole is in the synthesis of magnolol.

Safety

Estragole is suspected to be carcinogenic and genotoxic, as is indicated by a report of the European Union Committee on Herbal Medicinal Products. [4] 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. [4]

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." [5]

See also

Related Research Articles

<span class="mw-page-title-main">Tarragon</span> Species of flowering plant in the daisy family Asteraceae

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.

<span class="mw-page-title-main">Anise</span> Species of flowering plant

Anise, also called aniseed or rarely anix is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and Southwest Asia.

<span class="mw-page-title-main">Fennel</span> Flowering plant species in the carrot family

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.

<span class="mw-page-title-main">Basil</span> Important culinary herb

Basil, also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also known as sweet basil or Genovese basil. Basil is native to tropical regions from Central Africa to Southeast Asia. In temperate climates basil is treated as an annual plant, however, basil can be grown as a short-lived perennial or biennial in warmer horticultural zones with tropical or Mediterranean climates.

<span class="mw-page-title-main">Safrole</span> Chemical compound

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.

<span class="mw-page-title-main">Eugenol</span> Chemical compound

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.

<i>Dysphania ambrosioides</i> Species of flowering plant

Dysphania ambrosioides, formerly Chenopodium ambrosioides, known as Jesuit's tea, Mexican-tea, payqu(paico), epazote, mastruz, or herba sanctæ Mariæ, is an annual or short-lived perennial herb native to Central America, South America, and southern Mexico.

<span class="mw-page-title-main">Anethole</span> Chemical compound

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 plants in essential oils. 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.

<span class="mw-page-title-main">Cicely</span> Genus of flowering plants in the celery family Apiaceae

Myrrhis odorata, with common names cicely, sweet cicely, myrrh, garden myrrh, and sweet chervil, is a herbaceous perennial plant belonging to the celery family Apiaceae. It is the only species in the genus Myrrhis.

<span class="mw-page-title-main">Boldo</span> Species of plant

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.

<span class="mw-page-title-main">Apiole</span> Chemical compound

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.

<span class="mw-page-title-main">Galbanum</span>

Galbanum is an aromatic gum resin and a product of certain umbelliferous Persian plant species in the genus Ferula, chiefly Ferula gummosa and Ferula rubricaulis. Galbanum-yielding plants grow plentifully on the slopes of the mountain ranges of northern Iran. It occurs usually in hard or soft, irregular, more or less translucent and shining lumps, or occasionally in separate tears, of a light-brown, yellowish or greenish-yellow colour. Galbanum has a disagreeable, bitter taste, a peculiar, a somewhat musky odour, and an intense green scent. With a specific gravity of 1.212, it contains about 8% terpenes; about 65% of a resin which contains sulfur; about 20% gum; and a very small quantity of the colorless crystalline substance umbelliferone. It also contains α-pinene, β-pinene, limonene, cadinene, 3-carene, and ocimene.

<i>Syzygium anisatum</i> Species of tree

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.

<i>Tagetes lucida</i> Species of flowering plant

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.

<span class="mw-page-title-main">Bergamot essential oil</span> Cold-pressed essential oil

Bergamot essential oil is a cold-pressed essential oil produced by cells inside the rind of a bergamot orange fruit. It is a common flavoring and top note in perfumes. The scent of bergamot essential oil is similar to a sweet light orange peel oil with a floral note.

<span class="mw-page-title-main">Dianethole</span> Chemical compound

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.

<span class="mw-page-title-main">Spice use in antiquity</span>

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.

<span class="mw-page-title-main">Photoanethole</span> Chemical compound

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.

<i>Ocimum basilicum <span style="font-style:normal;">var.</span> minimum</i> Variety of basil

Greek basil is a flowering herb and cultivar of basil.

References

  1. 1 2 Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst. "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_141. ISBN   978-3527306732..
  2. Ashurst, Philip R. (1999). Food Flavorings. Springer. p. 11. ISBN   9780834216211.
  3. "Regulation EC 1334/2008".
  4. 1 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/docs/en_GB/document_library/Scientific_guideline/2010/04/WC500089960.pdf Archived 2015-07-22 at the Wayback Machine
  5. SCF/CS/FLAV/FLAVOUR/6, 26 September 2001, Opinion of the Scientific Committee on Food on Estragole (1-Allyl-4-methoxybenzene) "Archived copy" (PDF). Archived from the original (PDF) on 2007-03-02. Retrieved 2007-02-16.{{cite web}}: CS1 maint: archived copy as title (link)