Vanillylacetone

Description

Gingerol (correctly, [6]-gingerol) is the predominant phenol and most important of the pungent constituents in ginger oil. It was isolated by J. C. Thresh in 1879 from the rhizome of the ginger plant (Zingiber officinale). It and its dehydrated analogue [6]-shogaol are the primary ginger-derived bioactive compounds. Shogaol and the fragmented molecule zingerone are produced when fresh ginger is heated or cooked.?A recently synthesized azagingerol analogue?increases metabolism in mice and may reduce the risk of obesity-associated diseases.
Zingerone gives ginger a "hot" taste. It''s also an antioxidant, although it only weakly inhibits peroxidation of phospholipid liposomes in the presence of Fe(III) and ascorbate. Zingerone''s vanillin foundation and hydrocarbon tail make it a chemical relative of?eugenol?and capsaicin.

Chemical properties

White solid. Soluble in ether; sparingly soluble in water and petroleum ether.

Chemical properties

Zingerone has a strong, pungent odor reminiscent of ginger. It has a sharp taste, similar to ginger.

Occurrence

Reported found in the essential oil of Zingiber officinale. Also reported found in cranberry, raspberry, ginger and mango.

The Uses of Vanillylacetone

Vanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against li ver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes.

The Uses of Vanillylacetone

In fragrances, flavors and cosmetics; in artificial spice oils.

The Uses of Vanillylacetone

Vanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against liver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes.

Definition

ChEBI: A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.

Preparation

By condensation of vanillin with acetone followed by hydrogenation.

Aroma threshold values

Aroma characteristics at 10.0%: low impacting, creamy, spicy eugenol clove-like with a slight balsamic vanilla-like note.

Taste threshold values

Taste characteristics at 80 ppm: spicy with a biting, lingering heat. Taste characteristics at 20 ppm in 5% sugar solution: smooth, sweet, creamy and warm, spicy clove with a slight lingering burning bite.

Safety Profile

Moderately toxic by ingestion. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.