Description
4-(p-Methoxyphenyl)-2-butanone has an intensely sweet, floral,
fruity odor and a cherry-raspberry flavor at low concentrations.
May be prepared by condensing acetone with anisaldehyde to yield anisylidene acetone and subsequent hydrogenation in the presence
of Pd catalyst.
Chemical Properties
4-(p-Methoxyphenyl)-2-butanone has an intensely sweet, floral,fruity odor and cherry–raspberry flavor at low concentrations.
Chemical Properties
4-(4-Methoxyphenyl)-2-butanone is a clear colourless to pale yellow liquid. B.P. 277℃. Solidifies
in the cold, melts again at 10℃. Very slightly soluble in water, soluble in
alcohol and oils, poorly soluble in Propylene
glycol. Intensely sweet, floral and slightly fruity,
Cherry-preserve-like odor of good tenacity.
It has considerable resemblance to Heliotropine in its overall performance in a composition. Pleasant, sweet-fruity, Cherry-Raspberry-type flavor at concentrations below 40 ppm.
Tends to appear "perfumey" at levels higher
than 100 ppm.
Occurrence
Contained (approximately 53% level) in the odorous principle obtained by extraction and hydrolysis from aloe
wood (Aquilaria algallocha Roxb.) and in anise.
Uses
4-(4-Methoxyphenyl)-2-butanone is used as pharmaceutical intermediate.
Uses
4-(4-Methoxyphenyl)-2-butanone is used in insect attractants, organic synthesis, flavoring. This ketone, a methylether of a very popular
material (see para-Hydroxy phenylbutanone),
finds use in perfume compositions as a modifier for Heliotropine, a sweetener for Cyclamen aldehyde, and a blender in many types
of sweet florals, Fougeres, Oriental fragrances,
etc. It suffers from the drawback of being
considerably more expensive than Heliotropine, and it can therefore not truly be
classified as a substitute for that material. It
shows less tendency of discoloration in combination with the materials normally causing
such trouble with Heliotropine. It is also used in flavor compositions, particularly in Raspberty and Cherry,
two flavors which are commonly used as
targets for fantasy fragrances for Iipst ick perfumes. As a sweetener, it modifies Anise and
Anethole in licorice flavor compositions, and
it is generally used in smaller amounts in
many imitation fruit flavors for baked goods
or hard candy, where heat stability is essential.
Preparation
By condensing acetone with anisaldehyde to yield anisylidene acetone and subsequent hydrogenation in the presence of
Pd catalyst. It can also be prepared from Methyl vinyl
ketone by catalytic condensation with Phenol,
followed by Methylation.
Definition
ChEBI: 4-(4-Methoxyphenyl)-2-butanone is a member of methoxybenzenes.
Aroma threshold values
Aroma characteristics at 5.0%: sweet, fruity, woody, powdery, honey, vanilla, raspberry and ionone-like.
Taste threshold values
Taste characteristics at 40 ppm: floral, woody, ionone, raspberry, fruity, spice and berry.
Safety Profile
Low oral and skin
toxicity. A flammable liquid. When heated
to decomposition it emits acrid smoke and
irritating fumes.
