Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate
[CAS# 96562-58-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate
• Synonyms: methyl (2R)-2-(4-hydroxyphenoxy)propanoate
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.20
• CAS Registry Number: 96562-58-2
• EC Number: 411-950-4
• SMILES: C[C@H](C(=O)OC)OC1=CC=C(C=C1)O

Properties

• Melting point: 64-67 °C
• alpha: 43

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H318-H412
• Safety Statements: P264+P265-P273-P280-P305+P354+P338-P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate, commonly known as the methyl ester of (R)-(+)-2-(4-hydroxyphenoxy)propionic acid, is a notable compound in the field of organic chemistry. This chiral molecule is distinguished by its specific enantiomeric form and has important implications in both pharmaceuticals and chemical synthesis.

The discovery of Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate is rooted in the study of fenofibrate, a fibric acid derivative used to manage cholesterol levels. Fenofibrate is a prodrug that is metabolized in the body to form fenofibric acid. The (R)-enantiomer of fenofibric acid is known for its superior biological activity, and its methyl ester derivative, Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate, retains this characteristic efficacy.

One of the primary applications of Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate is in the synthesis of pharmaceuticals. Its chiral center plays a crucial role in the synthesis of enantiomerically pure compounds, which are vital for developing effective and selective drugs. The compound’s ability to enhance the stability and biological activity of drug molecules makes it a valuable intermediate in pharmaceutical synthesis. It is particularly useful in designing drugs with improved efficacy and reduced side effects.

In addition to its role in drug synthesis, Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate has applications in the development of agrochemicals. The chiral nature of this compound can influence the behavior of pesticides and herbicides, potentially leading to more effective and environmentally friendly agricultural products. Its use in creating selective agrochemical agents can enhance crop protection and yield, contributing to sustainable agriculture.

Furthermore, Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate is valuable in chemical research for its role in studying chirality and stereochemistry. The compound’s properties help scientists explore how different enantiomers of a molecule can affect chemical reactions and biological interactions. This research is fundamental for the advancement of chiral chemistry and the development of new materials and drugs.

Overall, Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate is an important compound with diverse applications. Its role in pharmaceutical synthesis, agrochemical development, and chemical research underscores its significance in advancing both scientific understanding and practical applications. The continued study of this compound will likely yield further insights and innovations in various fields.

References

2018. Rapid Formation of Advanced Scaffolds from Phenols and Anilines. Synlett, 29(20).
DOI: 10.1055/s-0037-1610340

2016. Total Synthesis of (-)-Strychnopivotine. Synfacts, 12(8).
DOI: 10.1055/s-0035-1562294