Raspberry Ketone

Description

4-(p-Hydroxyphenyl)-2-butanone has a sweet, fruity, raspberry preserves odor. May be prepared by catalytic hydrogenation of phydroxy-benzylidene acetone in the presence of platinum black in ether or methanol or in the presence of palladium absorbed on charcoal.

Chemical properties

white to slightly yellow powder or needles

Chemical properties

4-(4-Hydroxyphenyl)-2-butanone is a highly characteristic component of raspberry aroma. It forms colorless crystals (mp 82–83°C) with a sweet, fruity odor strongly reminiscent of raspberries. Raspberry ketone is prepared by alkali-catalyzed condensation of the alkali salt of 4-hydroxybenzaldehyde and acetone, followed by selective hydrogenation of the double bond in the resulting 4-hydroxybenzalacetone. Other syntheses start from phenol, which is converted into 4-(4-hydroxyphenyl)-2-butanone with methyl vinyl ketone or with 4-hydroxy-2-butanone.

Chemical properties

4-(p-Hydroxyphenyl)-2-butanone has a sweet, fruity, raspberry preserves–type odor.

Occurrence

Reported found European cranberry, raspberry, blackberry, loganberry and sea buckthorn (Hippophae rhamnoides L.).

The Uses of Raspberry Ketone

Intermediates of Liquid Crystals

The Uses of Raspberry Ketone

The primary aroma compound of red raspberries, used in perfume compositions, shampoos, cosmetics and as a food additive. Also an impurity in the synthesis of Dobutamine (D494445).

The Uses of Raspberry Ketone

4-(4-Hydroxyphenyl)-2-butanone is used in perfumery, in cosmetics, and as a food additive to impart a fruity odor.

Definition

ChEBI: A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at position 4 by a hydroxy group. It is found in a variety of fruits including raspberries, blackberries and cranberries, and is used in perfumery and cosmetics.

Taste threshold values

Taste characteristics at 40 ppm: fruity, jamy, berry, raspberry, and blueberry with seedy, cotton candy nuances

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 1206, 1976 DOI: 10.1021/jo00869a026
Synthetic Communications, 19, p. 1109, 1989 DOI: 10.1080/00397918908051034

Flammability and Explosibility

Non flammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.