PROPENYL GUAETHOL

Chemical properties

Free-flowing, white powder; odor and taste similar to vanilla, but much more powerful.Very soluble in fats, edible solvents, and essential oils; very slightly soluble in water.

Chemical properties

PROPENYL GUAETHOL exists in (Z)- (mp 35–36°C), [876306-58-0], and in (E)- (mp 86°C), [63477-41-8] forms. The (E)-isomer has a sweet vanilla-like odor. Propenylguethol can be prepared from isosafrole by reaction with methylmagnesium chloride or by ethylation of isoeugenol followed by selective demethylation with alkali .

Chemical properties

Propenylguaethol has a vanilla-like odor and flavor.

The Uses of PROPENYL GUAETHOL

Artificial vanilla flavoring, flavor enhancer.

The Uses of PROPENYL GUAETHOL

trans-2-Ethoxy-5-(1-propenyl)phenol was used in the synthesis of 2S-((E)-2-ethoxy-5-propenyl-phenoxy)-1-(3,4,5-trimethoxy-phenyl)-propane-1-one.

Preparation

By alkaline hydrolysis of 1-ethoxy-2-methoxy-4-propenyl benzene in ethanol or methanol solution at 150 to 190°C under pressure; or in ethylene glycol solution at the same temperature under atmospheric pressure; by saponification and contemporary transposition of the double bond starting from 1-ethoxy-2-methoxy-4-allyl benzene.

Definition

ChEBI: 2-Ethoxy-5-(1-propenyl)phenol is an aromatic ether.

Aroma threshold values

Detection: 400 ppb. Aroma characteristics at 1.0%: vanilla, sweet, spicy, slightly phenolic with a heliotropine- like creaminess.

Taste threshold values

Taste characteristics at 25 ppm: vanilla, spicy, sweet nutty, anisic with a biting creaminess.

Synthesis Reference(s)

Synthetic Communications, 21, p. 379, 1991 DOI: 10.1080/00397919108016759

Biochem/physiol Actions

Taste at 25 ppm