Methyl (R)-(+)-lactate
[CAS# 17392-83-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl (R)-(+)-lactate
• Synonyms: methyl (2R)-2-hydroxypropanoate
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.10
• CAS Registry Number: 17392-83-5
• EC Number: 241-420-6
• SMILES: C[C@H](C(=O)OC)O

Properties

• Density: 1.09
• Boiling point: 144-145 ºC
• Refractive index: 1.412-1.414
• Flash point: 49 ºC
• alpha: 8.5 º (c=neat)
• Water solubility: miscible, hydrolyses

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Hazard Statements: H226-H335-H319
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P261-P264+P265-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P319-P337+P317-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 3272

Discovory and Applicatios

Methyl (R)-(+)-lactic acid, a chiral ester with the chemical formula C4H8O3, is a compound of great industrial and research interest. Known for its pleasant fruity odor and high solubility, this substance has a wide range of applications, particularly in the pharmaceutical, agrochemical, and flavor and fragrance industries.

The discovery and synthesis of methyl (R)-(+)-lactic acid can be traced back to advances in stereochemistry and organic synthesis methods in the early 20th century. As scientists began to understand the importance of chirality in biochemical processes, they sought efficient methods to produce enantiomerically pure compounds. Methyl (R)-(+)-lactic acid, derived from the esterification of (R)-lactic acid, is a valuable compound due to its chiral purity and functional versatility.

One of the major applications of methyl (R)-(+)-lactic acid is in the pharmaceutical industry. Its role as a chiral building block makes it an integral part of the synthesis of a variety of active pharmaceutical ingredients (APIs). Many drugs require a specific enantiomer to exert their biological activity, and methyl (R)-(+)-lactic acid provides a reliable starting material for the production of these enantiomerically pure compounds. For example, it is used in the synthesis of anti-inflammatory drugs, antibiotics, and cardiovascular drugs. The enantiomeric purity of methyl (R)-(+)-lactic acid ensures that the resulting drug has the desired efficacy and reduces side effects.

In the field of agrochemicals, methyl (R)-(+)-lactic acid can be used as a precursor for the synthesis of herbicides and pesticides. The chirality of these compounds often plays a crucial role in their effectiveness and environmental impact. Using methyl (R)-(+)-lactic acid as a chiral starting material can develop agrochemicals that are not only more effective but also less harmful to non-target organisms and the environment.

The flavor and fragrance industry also benefits from the unique properties of methyl (R)-(+)-lactic acid. Its pleasant fruity aroma makes it an ideal ingredient in a variety of flavor and fragrance formulations. It is often used in the production of perfumes to impart a fresh, sweet scent to perfumes. In addition, it is used in food flavoring to enhance the fruity flavor of products such as confectionery, beverages, and baked goods. The high solubility of methyl (R)-(+)-lactic acid in water and organic solvents further increases its versatility in these applications.

Another notable application of methyl (R)-(+)-lactic acid is in the field of green chemistry. As industry moves toward more sustainable practices, the demand for environmentally friendly solvents and intermediates is increasing. Methyl (R)-(+)-lactic acid is well suited to this paradigm, as it is biodegradable and derived from renewable resources such as corn or sugar cane. It can be used as a solvent in a variety of chemical reactions, providing a more environmentally friendly alternative to traditional petroleum-based solvents.

The synthesis of methyl (R)-(+)-lactic acid typically involves the esterification of (R)-lactic acid with methanol. Advances in catalysis and process engineering have made the production method more efficient and selective, ensuring high enantiomeric purity and yield. These improvements have made methyl (R)-(+)-lactic acid more accessible for industrial use, further expanding its range of applications.

References

1994. Enantioselective hydrogenation of α-ketoesters over Pt/alumina modified with cinchonidine: theoretical investigation of the substrate-modifier interaction. Catalysis Letters, 27(1-2).
DOI: 10.1007/bf00811362

2024. Total Synthesis of Amycolamicin. Modern Natural Product Synthesis.
DOI: 10.1007/978-981-97-1619-7_2

1999. Synthesis of Cbz-Protected Ketomethylene Dipeptide Isosteres. Methods in Molecular Medicine, 23.
DOI: 10.1385/0-89603-517-4:103