ISOSAFROLE

Description

Isosafrole has an anise odor. It may be synthesized by alkaline isomerization of safrole using KOH at the boil or an alcoholic NaOH solution at room temperature under pressure.

Chemical properties

CLEAR SLIGHTLY YELLOW LIQUID

Chemical properties

Isosafrole has an anise-like odor. Use of isosafrole in foods is not permitted in the United States

Occurrence

Of the two isomers (cis- and trans-), the trans-form is the more stable and has been isolated in the pure state, probably occurring in the essential oil of ylang-ylang; it has been identified in the oils of Illicium religiosum and Ligusticum acutilobum Sieb. and Zucc.

The Uses of ISOSAFROLE

Manufacture of heliotropin, perfumes, flavors, pesticide synergists.

Preparation

From safrole by treatment with potassium or sodium hydroxide in the dry state or alcoholic solution, under pressure or at atmospheric pressure (Arctander, 1969).

Definition

ChEBI: Isosafrole is a member of benzodioxoles.

General Description

Colorless fragrant liquid with odor of anise. Used in small quantities in root beer and sarsaparilla flavors.

Reactivity Profile

ISOSAFROLE may react with strong reducing agents.

Hazard

Questionable carcinogen.

Synthesis

iso-SAFROLE is synthesized from Safrole by treatment with Potassium or Sodium hydroxide in dry state or alcoholic solution, under pressure or at atmospheric pressure.

Metabolism

On oxidation, isosafrole gives rise initially to an allyl alcohol and another, unidentified, conjugated alcohol, which are further oxidized to the vinyl ketone and piperonyl acrolein, respectively. Condensation of On oxidation, isosafrole gives rise initially to an allyl alcohol and another, unidentified, conjugated alcohol, which are further oxidized to the vinyl ketone and piperonyl acrolein, respectively. Condensation of the vinyl ketone with an amine would then lead to the formation of tertiary aminomethylenedioxypropiophenones (Mannich bases) (McKinney, Oswald, Fishbein & Walker, 1972).