16909-09-4

Basic information

• Product Name: 2,4-DIMETHOXYCINNAMIC ACID
• Synonyms: TRANS-2,4-DIMETHOXYCINNAMIC ACID;OTAVA-BB BB7015052308;RARECHEM BK HW 0035;(E)-3-(2,4-DIMETHOXY-PHENYL)-ACRYLIC ACID;LABOTEST-BB LT00233166;AURORA 11294;2,4-DIMETHOXYCINNAMIC ACID, TRANS;(2E)-3-(2,4-DIMETHOXYPHENYL)ACRYLIC ACID
• CAS NO: 16909-09-4
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• EINECS: 240-955-2
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives;C11 to C12;Carbonyl Compounds;Carboxylic Acids
• Mol File: 16909-09-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 192-194 °C(lit.)
• Boiling Point: 384℃
• Flash Point: 152℃
• Appearance: Solid
• Density: 1.203
• Vapor Pressure: 1.35E-06mmHg at 25°C
• Refractive Index: 1.573
• PKA: 4.60±0.13(Predicted)
• CAS DataBase Reference: 2,4-DIMETHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHOXYCINNAMIC ACID(16909-09-4)
• EPA Substance Registry System: 2,4-DIMETHOXYCINNAMIC ACID(16909-09-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 16909-09-4(Hazardous Substances Data)

Usage

Description

2,4-Dimethoxycinnamic acid is an organic compound that belongs to the class of cinnamic acids. It features a cinnamic acid core with two methoxy substituents on the benzene ring, which contributes to its unique chemical properties and potential applications across various industries.

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,4-Dimethoxycinnamic acid is used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Food and Beverage Industry:
Due to its antioxidant properties, 2,4-dimethoxycinnamic acid is used as a preservative and flavor enhancer in the food and beverage industry. Its ability to neutralize free radicals can help extend the shelf life of products and maintain their quality.
Used in Anti-Inflammatory and Antibacterial Applications:
2,4-Dimethoxycinnamic acid has been studied for its potential anti-inflammatory and antibacterial effects, making it a promising candidate for the development of new therapeutic agents. Its ability to modulate inflammatory responses and inhibit bacterial growth could lead to novel treatments for various conditions.
Overall, 2,4-dimethoxycinnamic acid has multiple applications in various industries, including pharmaceuticals, agrochemicals, food and beverages, and therapeutics. Its unique properties and potential for further research and development make it a valuable compound for future innovations.

InChI:InChI=1/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)10(7-9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4+

Upstream product

• 110-89-4 piperidine 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 531-59-9 7-methoxycoumarin 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 141-82-2 malonic acid 
• 74-88-4 methyl iodide 
• 108-24-7 acetic anhydride 
• 66417-42-3 (E)-3-(2,4-dimethoxy-phenyl)-acrylic acid methyl ester 
• 42174-73-2 (E)-2,4-dimethoxycinnamic acid ethyl ester 

Downstream Products

• 531-95-3 equol 
• 221054-79-1 (+)-Equol 
• 108-46-3 recorcinol 

Relevant articles and documents

2-Hydroxy-4-methoxy-trans-cinnamic Acid as a Precursor of Herniarin in Artemisia dracunculus

The isolation of (E)-2-hydroxy-4-methoxycinnamic acid (1) from Artemisia dracunculus L. supports strongly the assumption that this compound is an intermediate in the biosynthesis of 7-methoxycoumarin (herniarin, 3).The structure of the UV-unstable compound 1 was derived from 1H-NMR data and by comparison of the stable dimethylated derivative with synthetic (E)-2,4-dimethoxycinnamic acid methyl ester (2). - Keywords: Coumarins; Biosynthesis; Herniarin; Artemisia dracunculus; Compositae

Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents

Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with “oxadiazole”. A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound 32 displayed potent anti-tubercular activity (IC50 = 0.045 μg/mL). Molecular docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the experimental findings providing a platform for structure based hit-to-lead development.

Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors

A series of novel sulfonamides incorporating phenylacrylamido functionalities were synthesized and investigated for the inhibition of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). The physiologically and pharmacologically relevant human (h) isoforms hCA I and II (cytosolic isozymes), as well as the transmembrane tumor-associated hCA IX and XII were included in the study. These compounds showed low nanomolar or sub-nanomolar inhibition constants against hCA II (KIs in the range of 0.50–50.5 nM), hCA IX (KIs of 1.8–228.5 nM), and hCA XII (KIs of 3.5–96.2 nM) being less effective as inhibitors of the off target isoform hCA I. A detailed structure–activity relationship study demonstrates that the nature and position of substituents present on the aromatic part of the scaffold strongly influence the inhibition of CA isoforms. As hCA II, IX and XII are involved in pathologies such as glaucoma and hypoxic, and metastatic tumors, compounds of the type reported in this work may be useful preclinical candidates.