2596-47-6

Basic information

• Product Name: 4-ACETOXY-3-METHOXYCINNAMIC ACID
• Synonyms: 4-ACETYLFERULIC ACID;4-ACETOXY-3-METHOXYCINNAMIC ACID;3-METHOXY-4-ACETOXYCINNAMIC ACID;AKOS B004360;ACETYLFERULIC ACID;RARECHEM AL BK 0061;4-Acetoxy-3-methoxycinnamic acid, 98+%;4-Acetoxy-2-methoxycinnamic
• CAS NO: 2596-47-6
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22
• EINECS: 226-415-9
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 2596-47-6.mol
• Article Data: 91

Chemical Properties

• Melting Point: 193-196°C
• Boiling Point: 372℃
• Flash Point: 142℃
• Appearance: /
• Density: 1.265
• Vapor Pressure: 3.44E-06mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.32±0.10(Predicted)
• BRN: 2218026
• CAS DataBase Reference: 4-ACETOXY-3-METHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETOXY-3-METHOXYCINNAMIC ACID(2596-47-6)
• EPA Substance Registry System: 4-ACETOXY-3-METHOXYCINNAMIC ACID(2596-47-6)

Safety Data

• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2596-47-6(Hazardous Substances Data)

Usage

Description

4-ACETOXY-3-METHOXYCINNAMIC ACID, also known as ferulic acid acetate, is an organic compound derived from the formal condensation of the phenolic group of ferulic acid with acetic acid. It is an acetate ester with potential applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
4-ACETOXY-3-METHOXYCINNAMIC ACID is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-ACETOXY-3-METHOXYCINNAMIC ACID serves as a valuable building block for the creation of more complex molecules. Its reactivity and functional groups make it a versatile starting material for the synthesis of a wide range of organic compounds.
Used in Flavor and Fragrance Industry:
4-ACETOXY-3-METHOXYCINNAMIC ACID is used as a key ingredient in the flavor and fragrance industry. Its unique aromatic properties contribute to the development of various scents and flavors, enhancing the sensory experience of consumer products.
Used in Material Science:
In material science, 4-ACETOXY-3-METHOXYCINNAMIC ACID can be utilized in the development of novel materials with specific properties. Its chemical structure can be manipulated to create materials with enhanced mechanical, thermal, or electrical properties, depending on the desired application.
Used in Research and Development:
4-ACETOXY-3-METHOXYCINNAMIC ACID is also used in research and development settings, where it can be studied for its potential applications in various fields. Scientists and researchers can explore its chemical properties and reactivity to develop new methods and techniques for synthesizing other compounds or materials.

InChI:InChI=1/C12H12O5/c1-8(13)17-10-5-3-9(4-6-12(14)15)7-11(10)16-2/h3-7H,1-2H3,(H,14,15)/b6-4+

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 121-33-5 vanillin 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 64-19-7 acetic acid 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 881-68-5 vanillin acetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 141-82-2 malonic acid 
• 28028-62-8 ethyl ferulate 
• 331-39-5 caffeic acid 
• 331-39-5 caffeic acid 

Downstream Products

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 10543-12-1 4-acetoxy-3-methoxybenzoic acid 
• 55882-65-0 4-acetoxyferuloyl chloride 
• 121-33-5 vanillin 
• 55417-34-0 3-(4-(ethanoyloxy)-3-methoxyphenyl)propanoic acid 
• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 46316-15-8 4-acetoxy-3-methoxyvinylbenzene 
• 6635-27-4 ethyl (E)-3-(4-acetoxy-3-methoxyphenyl)-prop-2-enoate 
• 50906-14-4 N,N'-bisferuloyl 1,2-diaminoethane 
• 50906-13-3 N,N'-acetylferuloyl-1,2-diaminoethane 
• 19856-65-6 3-(4-hydroxy-3-methoxyphenyl)-1-morpholinoprop-2-en-1-one 
• 38448-13-4 3-(4-hydroxy-3-methoxyphenyl)-1-(pyrrolidin-1-yl)prop-2-en-1-one 
• 85708-49-2 N-phenethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide 

Relevant articles and documents

A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives

A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.

Oat polyphenol avenanthramide-2c confers protection from oxidative stress by regulating the Nrf2-ARE signaling pathway in PC12 cells

Accumulating evidence has demonstrated that cellular antioxidant systems play essential roles in retarding oxidative stress-related diseases, such as Parkinson's disease. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is a chief regulator of c

Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum

Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.