Description
2-Methyl-3-(p-isopropylphenyl) propionaldehyde has a strong,
flowery odor. May be prepared by condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst.
Chemical Properties
The commercially available racemate is a colorless to yellowish liquid with an intense floral odor reminiscent of Cyclamen europaeum (cyclamen, sowbread).
Production. Two main processes are used for the industrial synthesis of cyclamen aldehyde:
1) Alkaline condensation of 4-isopropylbenzaldehyde and propanal results, via the aldol, in the formation of 2-methyl-3-(4-isopropylphenyl)-2-propenal. The unsaturated aldehyde is hydrogenated selectively to the saturated aldehyde in the presence of potassium acetate and a suitable catalyst, such as palladium–alumina:
2) Friedel–Crafts reaction of isopropylbenzene and 2-methylpropenal diacetate (methacrolein diacetate) in the presence of titanium tetrachloride/boron trifluoride etherate gives cyclamen aldehyde enolacetate, which is hydrolyzed to aldehyde:
Uses. Cyclamen aldehyde is an important component for obtaining special blossomnotes in perfume compositions, particularly the cyclamen type. Because of its fresh, floral aspect, it is also used as the top note in many other blossomfragrances.
Chemical Properties
2-Methyl-3-(p-isopropylphenyl)-propionaldehyde has a strong, flowery odor
Occurrence
Reported found in nutmeg and starfruit.
Uses
Cyclamal, is an ingredient in perfume. It can also be used in the synthesis of Cyclamen Alcohol (C987655).
Uses
Cyclamen Aldehyde is a very powerful, floral, green note used in many perfumery applications to blend into fresh, floral, green or ozonic/marine accords. It is an ingredient with growing use and importance in helping to build replacement accords for materials disappearing from the Perfumers’ palette. Cyclamen has good overall stability except in extremes of pH. It has good tenacity and substantivity and represents very good value for money in new creations.In addition to its use in numerous perfume compositions, cyclamen aldehyde is an intermediate for the preparation of fungicides and fungistatic substances.
Preparation
By condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst
Definition
ChEBI: Xi-3-(4-Isopropylphenyl)-2-methylpropanal is a monoterpenoid.
Safety Profile
Moderately toxic by
ingestion. A human skin irritant. See also
ALDEHYDES. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Synthesis
Cyclamen aldehyde is synthesized from Cuminaldehyde plus Ropionaldehyde by condensation followed by selective hydrogenation and finally dehydrogenation of the Cyclamen alcohol to aldehyde.
