3893-15-0

Usage

Uses

Used in Food and Beverage Industry:
2-Propenal, 2-Methyl-3-(4-Methylphenyl)is used as a flavoring agent for its cinnamon-like taste and aroma, enhancing the flavor profiles of a wide range of food and beverage products.
Used in Perfumery and Fragrance Industry:
Cinnamaldehyde is utilized in the production of perfumes, fragrances, and essential oils, capitalizing on its pleasant and long-lasting scent to create appealing olfactory experiences.
Used in Traditional Medicine:
2-Propenal, 2-Methyl-3-(4-Methylphenyl)has demonstrated anti-inflammatory and antioxidant properties, making it a valuable component in traditional medicine for treating various ailments and promoting overall health.
Used as a Natural Preservative:
Due to its antimicrobial properties, cinnamaldehyde is employed as a natural preservative in a variety of products, extending their shelf life and maintaining freshness without the use of synthetic additives.
While the provided materials do not specify different industries for each application, the uses listed above cover the primary areas where 2-Propenal, 2-Methyl-3-(4-Methylphenyl)-, or cinnamaldehyde, is commonly applied. Its multifaceted utility underscores its importance in various sectors, from enhancing consumer products to contributing to health and wellness.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 123-38-6 propionaldehyde 
• 78-84-2 isobutyraldehyde 
• 108-88-3 toluene 
• 119346-67-7 ethyl (E)-2-methyl-3-(p-tolyl)acrylate 
• 56138-10-4 (2E)-2-methyl-3-(4-methylphenyl)-2-propen-1-ol 
• 113237-60-8 [(E)-2-Methyl-3-p-tolyl-prop-2-en-(E)-ylidene]-phenyl-amine 
• 154581-92-7 (Z)-2-Trimethylsilanyl-1-trimethylsilanyloxy-propene 

Downstream Products

• 56138-10-4 2-methyl-3-(p-tolyl)prop-2-en-1-ol 
• 1392325-28-8 ethyl (E)-6-(4-methylphenyl)-2-ethyl-5-methyl-3,4-dioxohex-5-enoate 
• 1392325-19-7 C₂₅H₃₇NO₄Si 
• 1589518-73-9 N-(2,6-dimethyl-1H-inden-1-yl)-4-methylbenzenesulfonamide 
• 1428319-33-8 (E)-1-cyclohexenyl-2-methyl-3-p-tolylprop-2-en-1-ol 
• 1428319-55-4 C₁₇H₂₀Br₂O 
• 1428319-49-6 C₁₇H₂₀O 
• 1428319-21-4 (E)-1-cyclohexenyl-2-methyl-3-p-tolylprop-2-en-1-ol 
• 1300662-42-3 (E)-2-Methyl-3-(4methylphenyl)-2-propenyl Formate 
• 1226914-57-3 1-[(1E)-3-(Allyloxy)-2-methyl-1-propenyl]-4-methylbenzene 
• 56138-10-4 (2E)-2-methyl-3-(4-methylphenyl)-2-propen-1-ol 
• 1228457-57-5 C₁₈H₂₇NOSi 

Relevant academic research and scientific papers

Asymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co–Catalyzed, Enantioselective Proton-Transfer

We report an enantioselective Nazarov cyclization catalyzed by chiral hydrogen-bond-donors in concert with silyl Lewis acids. The developed transformation provides access to tri-substituted cyclopentenones in high levels of enantioselectivity (up to 95% e.e.) from a variety of simple unactivated dienones. Kinetic and mechanistic studies are consistent with a reversible 4π-electrocyclization C?C bond-forming step followed by rate- and enantio-determining proton-transfer as the mode of catalysis. (Figure presented.).

Dehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups

An unprecedented cross-dehydrogenative-coupling (CDC) reaction of saturated aldehyde β-C-H with arenes to form cinnamaldehydes via the cleavages of four C-H bonds has been developed. The reaction possesses complete E-stereoselectivity for the C=C double bond. The protocol is featured by atom and step economy, mild reaction conditions, and convenient operation.

Gold(I)-Catalyzed 1,3-Carbofunctionalizations of Anthranils with Vinyl Propargyl Esters to Yield 1,3-Dihydrobenzo[ c]-isoxazoles

This work describes gold-catalyzed 1,3-carbofunctionalizations of anthranils with vinyl propargyl esters to form 1,3-dihydrobenzo[c]-isoxazoles. Excellent diastereoselectivity has been achieved to yield products containing three stereogenic carbons. These

Enantioselective Nazarov Cyclizations Catalyzed by an Axial Chiral C6F5-Substituted Boron Lewis Acid

A chiral variant of B(C6F5)3 with a 3,3′-disubstituted binaphthyl backbone is shown to catalyze Nazarov cyclizations with high levels of enantio- and diastereocontrol. The parent B(C6F5)3 a

A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes

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.

Poly(phosphoric acid) (PPA)-Promoted 5- exo -Cyclization of Iminium Ions Generated in Situ: A Facile Access to Functionalized Indene Derivatives

A metal-free Bronsted acid promoted two-component reaction between cinnamaldehydes and sulfonamides is described. This cascade process provides a simple and atom-economical alternative synthesis of a range of functionalized indenes from easily available starting materials. The resulting N -indenylsulfonamides were readily converted into the corresponding indenylenamines or indanones.

Assembly of indenamine derivatives through in situ formed N-sulfonyliminium ion initiated cyclization

An expedient route to structurally diverse indenamine derivatives through condensation of the readily accessible substituted cinnamylaldehydes and sulfonylamines under the catalysis of FeCl3 has been developed, featuring high efficiency in the generation of two bonds and one ring in a single-step and water as the only by-product. This journal is the Partner Organisations 2014.

Neutral nazarov-type cyclization catalyzed by palladium(0)

Joining the circle: The first Pd0 catalyzed Nazarov-type cyclization of diketoesters (see scheme) proceeds in 70 % to 95 % yield under strictly neutral pH conditions. Aryl substitution of the diketoesters is not required, so the reaction shows great versatility and can also proceed with aliphatic substrates. Copyright

An organocatalytic asymmetric nazarov cyclization

An organocatalytic asymmetric Nazarov cyclization of diketoesters that proceeds by means of a dual activation mechanism has been developed. Screening of a number of catalysts led to a new thiourea that incorporates a primary amino group. The method gives rise to cyclic products with two adjacent quaternary asymmetric carbon atoms, one of which is an all-carbon stereocenter, with complete or nearly complete diastereoselectivity and in high or very high enantiomeric excess. A brief and very convenient synthesis of the acyclic diketoester starting materials through nucleophilic addition to a ketene is also described.

Synthesis of substituted hexa-3,5-dienoic acid methyl esters from conjugated dienones

Substituted hexa-3,5-dienoic acid methyl esters (2) were conveniently prepared in one step by 1,2-carbonyl transposition of the corresponding dienones (1) using lead(IV) acetate and boron trifluoride-diethyl ether in benzene at room temperature.