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4-Allylanisole

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4-Allylanisole Basic information
4-Allylanisole Chemical Properties
  • Melting point:25°C
  • Boiling point:215-216 °C (lit.)
  • Density 0.965 g/mL at 25 °C (lit.)
  • FEMA 2411 | ESTRAGOLE
  • refractive index n20/D 1.521(lit.)
  • Flash point:178 °F
  • storage temp. Sealed in dry,2-8°C
  • solubility 0.178g/l
  • form Liquid
  • Specific Gravity0.965
  • color Clear colorless
  • Water Solubility 177.8mg/L(25 ºC)
  • Merck 14,3705
  • JECFA Number1789
  • BRN 1099454
  • Stability:Stable. Flammable. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference140-67-0(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzene, 1-methoxy-4-(2-propenyl)-(140-67-0)
  • EPA Substance Registry SystemEstragole (140-67-0)
Safety Information
MSDS
4-Allylanisole Usage And Synthesis
  • Chemical Propertiescolourless liquid with an aniseed smell
  • Chemical PropertiesBasil 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; n20D 1.5100–1.5200; α20D ?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 PropertiesEstragole has an odor reminiscent of anise with a corresponding sweet taste (differing from anethole)
  • Chemical PropertiesHerbaceous 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.
  • OccurrenceReported found in anise oil.
  • Usesinsect atttractant, skin irritant, carcinogen
  • UsesIn perfumes and as flavor in foods and liqueurs.
  • PreparationObtained 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.
  • CompositionThe 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 valuesTaste 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 DescriptionColorless 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 ReactionsForms azeotropic mixtures with water. . Insoluble in water.
  • Reactivity Profile4-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 HazardACUTE/CHRONIC HAZARDS: 4-Allylanisole is an irritant.
  • Fire Hazard4-Allylanisole is combustible.
  • Safety ProfileModerate 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.
4-Allylanisole Preparation Products And Raw materials
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