80-54-6 Usage
Description
Lily aldehyde (also known as lysmeral or Lilial) is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders1-3. 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
Different sources of media describe the Chemical Properties of 80-54-6 differently. You can refer to the following data:
1. 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.
2. 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
Different sources of media describe the Uses of 80-54-6 differently. You can refer to the following data:
1. 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.
2. 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
Nonflammable
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.
Check Digit Verification of cas no
The CAS Registry Mumber 80-54-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 80-54:
(4*8)+(3*0)+(2*5)+(1*4)=46
46 % 10 = 6
So 80-54-6 is a valid CAS Registry Number.
InChI:InChI=1/C14H20O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-8,10-11H,9H2,1-4H3/t11-/m0/s1
80-54-6Relevant articles and documents
Preparation method of high-quality para-lilial
-
, (2020/06/30)
The invention provides a preparation method of para-lilial. High-quality para-lilial is synthesized by using p-tert-butyl benzene halide and methacrylic acid as raw materials in the presence of a catalyst. The raw materials and the solvent used in the method are low in cost, the coupling reaction of tert-butyl benzene halide and methacrylic acid can be efficiently carried out under the action of the catalyst, expensive and complex catalyst ligands do not need to be used, and the manufacturing cost is greatly reduced. Besides, the purification process in the production process can effectively remove isomer impurities, the hydrogenation process is high in selectivity, a high-quality para-lilial product can be obtained, the process is simple and easy to control, and industrial production is facilitated.
Lily aldehyde preparation method
-
Paragraph 0039; 0040; 0044, (2018/04/03)
The invention discloses a lily aldehyde preparation method. Specifically, the lily aldehyde preparation method comprises the steps: (a) in an inert solvent and under existence of a catalyst and ligand, performing hydroformylation on compound shown by a formula II with hydrogen and carbon monoxide to form compound shown by a formula I. By means of the preparation method disclosed by the invention,high-purity lily aldehyde can be obtained, lily aldehyde production cost is reduced, and a production technology is simplified; furthermore, the preparation method is suitable for large-scale industrial production; thus, the preparation method has application value.
A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes
Vrbková, Eva,Vysko?ilová, Eli?ka,Rott, Martin,Zapletal, Martin,?erveny, Libor
, p. 2603 - 2613 (2017/03/22)
The 4-Alkyl-α-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-α-methylcinnamylaldehydes preparation with similar results. In the second step—hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.
