Lily aldehyde

Description

Lily aldehyde (also known as lysmeral or Lilial) is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders^1-3. It is fresh light green floral lily muguet lindenblossom aldehyde. Lilial is used in a wide variety of compositions where it confers a particularly recommended for floral notes such as muguet, linden-blossom and cyclamen².

Chemical Properties

Lilial is a colorless to pale yellow liquid, as yet has not been found in nature. It has a higher stability than the homologous cyclamenaldehyde and therefore is used as scent in soaps.

Lilial is a widely used fragrance compound found naturally in the essential oil of chamomile and is used synthetically in a variety of beauty products, including perfumes, shampoos, deodorants, tanning lotions and hairstyling products, primarily for its Lily of the Valley aroma.

Chemical Properties

Lily aldehyde is a homolog of cyclamenaldehyde. The racemic compound is a colorless to slightly yellow liquid with a mild-floral odor, reminiscent of cyclamen and lily of the valley.
The aldehyde is prepared by the same routes as cyclamenaldehyde.
Other routes start from ??-methylcinnamaldehyde. ??-Methylcinnamaldehyde (from benzaldehyde and propionaldehyde) is hydrogenated to ??-methyldihydrocinnamic alcohol.The alcohol is alkylated with tert-butyl chloride or isobutene to 4-tert-butyl-??-methyldihydrocinnamic alcohol, which is subsequently dehydrogenated to the desired aldehyde.
4-tert-Butyl-??-methyldihydrocinnamaldehyde is more stable than cyclamenaldehyde and is a popular component of flower compositions, particularly lily of the valley and linden types, because of its mild, pleasant, blossomfragrance. It is used in a wide range of perfume types, but especially in soap and detergent perfumes.

Uses

In addition to its applications in the perfume and aroma industry, lilial is used mainly for the synthesis of substituted 3-(4-tert-butylphenyl)-2-methylpropylamines, a new class of substances with fungicidal properties. These compounds are effective against mildew in barley and wheat.

Uses

2-(4-tert-Butylbenzyl)propionaldehyde may be used as a reference standard for the determination of 2-(4-tert-butylbenzyl)propionaldehyde in:

• Human urine samples by ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) equipped with electrospray ionization (ESI) source and multiple reaction monitoring (MRM) mode of detection.
• Deodorants and air fresheners by sonication extraction coupled with gas chromatography-mass spectrometry (GC-MS).
• Scented consumer products by GC-MS as well as GC in combination with olfactometry.

Production Methods

Lily aldehyde is produced industrially almost solely by aldol condensation of 4-tert-butylbenzaldehyde and propionaldehyde to give 4-tert-butyl-α-methylcinnamaldehyde, which can be hydrogenated selectively on noble metal catalysts such as Pd, Rh, Pd – Pr2O3 on Al2O3, or on modified cobalt catalysts. The aldol condensation and the hydrogenation can be carried out in one step in the presence of a hydrogenation catalyst.
The Friedel – Crafts reaction of 4-tertbutylbenzene with methacrolein or methacrolein diacetate proceeds in an analogous manner to the preparation of cyclamenaldehyde.
Further possibilities are the Rh-catalyzed hydroformylation of 1-(4-tert-butylphenyl)-1- methoxypropene and subsequent partial hydrogenation, the palladium salt catalyzed reaction of 4-tert-butylphenylhalide with methallylalcohol, and the dehydrogenation of 3-(4-tert-butylphenyl)-2-methylpropanol on silver catalysts.

General Description

2-(4-tert-Butylbenzyl)propionaldehyde is categorized under the synthetic fragrance class of compounds widely utilized in consumer products such as perfumes, after shave lotions, cosmetics, etc.

Flammability and Explosibility

Non flammable

Trade name

Lilestralis Pure (Innospec), Lysmeral® Extra (BASF).

Contact allergens

Lilial? is a synthetic compound listed as a fragrance allergen. Its presence is indicated on cosmetics within the EU.