3-(2,3,4-Trimethoxyphenyl)propanoic acid
[CAS# 33130-04-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 3-(2,3,4-Trimethoxyphenyl)propanoic acid
• Synonyms: 2,3,4-Trimethoxybenzenepropanoic acid
• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25
• CAS Registry Number: 33130-04-0
• EC Number: 251-389-0
• SMILES: COC1=C(C(=C(C=C1)CCC(=O)O)OC)OC

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 70-73 °C (Expl.)
• Index of Refraction: 1.516, Calc.^*
• Boiling Point: 362.3±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 134.8±20.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-(2,3,4-Trimethoxyphenyl)propanoic acid, also known as TMPA, is an organic compound that belongs to the class of phenylpropanoic acids. This compound features a phenyl ring with methoxy groups (-OCH3) attached to the 2, 3, and 4 positions, and a propanoic acid functional group at the 3-position. The presence of multiple methoxy groups on the aromatic ring significantly affects the compound's electronic properties, enhancing its reactivity and making it an interesting compound for various applications in organic synthesis and medicinal chemistry.

The discovery of 3-(2,3,4-trimethoxyphenyl)propanoic acid can be traced back to the interest in modifying phenylpropanoic acid derivatives for enhanced biological activities. Phenylpropanoic acids are a well-known class of compounds in medicinal chemistry due to their broad range of bioactivities, including anti-inflammatory, antioxidant, and anticancer properties. The introduction of methoxy groups in the aromatic ring often influences the biological profile of these compounds, making them valuable for the development of new therapeutic agents.

One of the key applications of 3-(2,3,4-trimethoxyphenyl)propanoic acid lies in its use as a precursor for the synthesis of bioactive compounds. The trimethoxyphenyl group, with its electron-donating effects, increases the reactivity of the molecule, making it a versatile intermediate for the design of novel molecules with desired pharmacological activities. The compound has been investigated for its potential as an anti-inflammatory agent, with studies suggesting that its biological effects may be related to its ability to modulate key signaling pathways involved in inflammation. In addition, the compound's antioxidant properties have been explored, as it has shown promise in reducing oxidative stress, a contributor to various chronic diseases, including cardiovascular diseases and neurodegenerative disorders.

3-(2,3,4-Trimethoxyphenyl)propanoic acid also holds potential as a lead compound for the development of novel anticancer drugs. Research has shown that the compound can inhibit the growth of certain cancer cell lines, likely through the modulation of cell cycle regulators and apoptotic pathways. The methoxy substitution on the phenyl ring may contribute to the compound's ability to interact with cellular targets, making it an attractive candidate for further exploration in anticancer drug discovery.

In addition to its therapeutic applications, 3-(2,3,4-trimethoxyphenyl)propanoic acid has potential uses in the field of agrochemicals. Its chemical structure suggests that it could be used as a building block for the development of herbicides, fungicides, or plant growth regulators. The ability to modify the compound further by altering the side chains or the methoxy groups could lead to enhanced selectivity and efficacy in agricultural applications.

In materials science, the compound's functional groups, especially the methoxy groups, could make it suitable for use in the design of functionalized polymers or other materials with specific properties. The trimethoxyphenyl group may also allow the compound to participate in various chemical reactions, leading to the creation of specialized coatings or adhesives.

In conclusion, 3-(2,3,4-trimethoxyphenyl)propanoic acid is a versatile compound with promising applications in medicinal chemistry, agrochemicals, and materials science. Its multiple methoxy groups enhance its reactivity and potential for further chemical modifications, making it an attractive building block for the synthesis of novel bioactive compounds and functional materials.

References

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