Estragole

Chemical properties

colourless liquid with an aniseed smell

Chemical properties

Basil oil, methyl chavicol (estragole)-type (Réunion type, exotic type) is obtained by steam distillation of the flowering tops or whole plants of Ocimum basilicum L. (Lamiaceae), which was formerly grown in Réunion and Madagascar. Today, the oil is produced in India and Vietnam on relatively large scale (～100 and 30 t/yr, respectively) and also in Egypt, but in small quantities. It is a light yellow liquid with a fresh, green, spicy odor characteristic of methyl chavicol (estragole).
d²⁰₂₀ 0.948–0.970; n²⁰_D 1.5100–1.5200; α²⁰_D ?1°to +2°; solubility: 1 vol in ≤7 vol 80% ethanol; content by GC: methyl chavicol 75–87%; linalool 0.5–3%(data for the classical “exotic” type; Indian types may contain up to ～20% linalool).

Chemical properties

Estragole has an odor reminiscent of anise with a corresponding sweet taste (differing from anethole)

Chemical properties

Herbaceous plant native to eastern and central Europe; it prefers shady growing sites. It grows 30 to 80 cm (12 to 31 in.) tall, with roots clustered in bundles, a branched stalk, alternate leaves and yellow flowers. Leaves are fragrant and anise-flavored. The plant flowers from July to August. The parts used are the flowering tops and leaves. Tarragon has a sweet, spicy odor and a sweet, anisic, fresh, green flavor reminiscent of basil and anise. This herb is commonly used to flavor vinegar and to season meats, soups, vegetable and fish dishes.

Occurrence

Reported found in anise oil.

The Uses of Estragole

4-Allylanisole has been used as a reference standard for the analysis of 4-allylanisole in essential oils by high performance liquid chromatography (HPLC) equipped with fluorometric detector and in emissions from live vegetation by solid-phase microextraction (SPME) combined with proton transfer reaction mass spectrometry (PTR-MS). It may be used as a reference standard for the determination of 4-allylanisole in food products by simultaneous distillation-extraction (SDE) followed by analyses using capillary gas chromatography (GC)-flame ionization detector (FID) and GC-MS.

The Uses of Estragole

insect atttractant, skin irritant, carcinogen

The Uses of Estragole

In perfumes and as flavor in foods and liqueurs.

What are the applications of Application

4-Allylanisole is a phenylpropene used in fragrances and the main component of basil oil

Preparation

Obtained by fractional distillation of the oil of turpentine or by treating a solution of the same oil in ether with an aqueous solution of mercuric acetate and subsequently heating the aqueous phase with zinc and sodium hydroxide; forms allyl bromide and magnesium p-methoxy phenate in ether.

Definition

ChEBI: Estragole is an olefinic compound.

Composition

The herb is reported to contain polyacetylenic compounds (capillene; phenyl-1,3-pentadiyne; acetylenic alcohol and its glucoside; capillone and dehydrofalcarinone); coumarinic and isocoumarinic derivatives (artemidinol, artemidiol, scopoletine, herciarine); alcohols (9-hydroxygeraniol; 4-methoxybenzyl alcohol); aldehyde (CoE, 2000).

Taste threshold values

Taste characteristics at 10 ppm: sweet, licorice, phenolic, weedy, spice, celery-like

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 1748, 1996 DOI: 10.1021/jo9518314
Synthesis, p. 701, 1983

General Description

Colorless liquid with odor of anise. Insoluble in water. Isolated from rind of persea gratissima grath. and from oil of estragon. Found in oils of Russian anise, basil, fennel turpentine, tarragon oil, anise bark oil.

Air & Water Reactions

Forms azeotropic mixtures with water. . Insoluble in water.

Reactivity Profile

4-Allylanisole may react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with both acids and bases.

Health Hazard

ACUTE/CHRONIC HAZARDS: 4-Allylanisole is an irritant.

Fire Hazard

4-Allylanisole is combustible.

Safety Profile

Moderate acute toxicity by many routes. A skin irritant. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS. A spice used in foods, liqueurs, and perfumes.