83071-67-4

Usage

Uses

Used in Chemical Synthesis Industry:
4-Acetoxy-3-methoxycinnamaldehyde is used as a synthetic intermediate for the production of various organic compounds and pharmaceuticals. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of complex molecules.
Used in Flavor and Fragrance Industry:
Due to its aromatic properties, 4-Acetoxy-3-methoxycinnamaldehyde is used as a flavoring agent and a fragrance ingredient in the food, beverage, and cosmetics industries. Its distinct scent and taste profile contribute to the creation of unique and appealing products.
Used in Pharmaceutical Industry:
4-Acetoxy-3-methoxycinnamaldehyde is utilized as a key component in the development of pharmaceutical drugs. Its chemical properties enable it to be incorporated into drug molecules, potentially leading to the discovery of new therapeutic agents with novel mechanisms of action.
Used in Research and Development:
In the field of scientific research, 4-Acetoxy-3-methoxycinnamaldehyde serves as a valuable compound for studying various chemical reactions and processes. Its reactivity and structural features make it an ideal candidate for exploring new synthetic pathways and understanding reaction mechanisms.

Upstream product

• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 458-36-6 trans-coniferyl aldehyde 
• 108-24-7 acetic anhydride 
• 881-68-5 vanillin acetate 
• 52509-14-5 (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide 
• 5912-87-8 (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene 
• 1006614-61-4 2-methoxy-4-(3-oxopropyl)phenyl ethanoate 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 69017-41-0 (E)-3-(4-acetoxy-3-methoxyphenyl)-2-propen-1-ol 
• 93-28-7 eugenol acetate 
• 97-53-0 4-allylguaiacol 

Downstream Products

• 458-36-6 trans-coniferyl aldehyde 
• 58045-88-8 3,4-dimethoxycinnamaldehyde 

Relevant academic research and scientific papers

DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids

Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.

A selective and mild glycosylation method of natural phenolic alcohols

Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.

Efficient preparation of trans-α,β-unsaturated aldehydes from saturated aldehydes by oxidative enamine catalysis

A mild and highly efficient amine-catalyzed, IBX-mediated oxidation of aldehydes to (E) selective α,β-unsaturated aldehydes has been achieved in good yields. The process features a new oxidation of enamines to iminium ions in a catalytic fashion.

Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes

Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials.

Facile Synthesis of 4-Hydroxycinnamyl p-Coumarates

Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine.

Synthesis of cinnamaldehydes by oxidation of arylpropenes with 2,3-dichloro-5,6-dicyanoquinone

Alkoxylated 1-aryl-1-propenes [1-(4-methoxyphenyl)-1-propene, 1-(3,4-dimethoxyphenyl)-1-propene, 1-(3,4,5-trimethoxyphenyl)-1-propene] and 3-aryl-1-propenes [3-(4-methoxyphenyl)-1-propene, 3-(3,4-dimethoxyphenyl)-1-propene 3-(3,4,5-trimethoxyphenyl)-1-propene] gave cinnamaldehydes in 71-84% yield on treatment with 2,3-dichloro-5,6-dicyanoquinone (DDQ) (slight excess) at room temperature for 0.5-2 h in the two-phase system dichloromethane-water (4:1). Arylpropenes lacking electron-donating alkoxy groups (1-phenyl-1-propene, 3-phenyl-1-propene) or carrying an acetoxy group [1-(4-acetoxy-3-methoxyphenyl)-1-propene, 3-(4-acetoxy-3-methoxyphenyl)-1-propene] were converted into cinnamaldehydes in low to moderate yields on oxidation with a large excess of DDQ in combination with long reaction times (> 12 h). All the 1-aryl-1-propones examined were rapidly converted into a mixture of mono-and bis-(3-aryl-2-propenyl) ethers of 2,3-dichloro-5,6-dicyanohydroquinone (DDHQ) on DDQ oxidation. The rate of formation of DDHQ ethers from alkoxy-substituted 3-aryl-1-propenes was slightly lower. 3-Phenyl-1-propene and also 3-(4-acetoxy-3-methoxyphenyl)-1-propene were largely unchanged at the initial stage of the oxidation. Significant differences in the compositions of the DDHQ ether mixtures obtained from 1-aryl-1-propenes and 3-aryl-1-propones were not observed. Acta Chemica Scandinavica 1998.

A mild synthesis of coumaryl, coniferyl, sinapyl aldehydes and alcohols

Acetylconiferyl aldehyde is obtained from acetylvanillin by a Wittig reaction under phase-transfer conditions; basic hydrolysis gives coniferyl aldehyde, or after reduction with sodium borohydride affords coniferyl alcohol. This method is extended to the sinapyl and coumaryl series.

Process of preparing pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxygenase inhibitors

The present invention is 3,5-substituted, isoxazoles, pyrazoles, isothiazoles, and analogs thereof having 5-lipoxygenase or cyclooxygenase inhibiting activity or as a sunscreen.