(R)-Glycidyl butyrate
[CAS# 60456-26-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: (R)-Glycidyl butyrate
• Synonyms: Oxiran-2-ylmethyl butyrate
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• CAS Registry Number: 60456-26-0
• EC Number: 611-977-3
• SMILES: CCCC(=O)OC[C@H]1CO1

Properties

• Density: 1.035
• Boiling point: 192.6 °C
• Refractive index: 1.427-1.429
• Flash point: 90 °C
• alpha: -30 ° (c=neat)
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H312-H315-H319-H334-H335
• Safety Statements: P233-P260-P261-P264-P264+P265-P270-P271-P280-P284-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

(R)-Glycidyl butyrate is an enantiomerically pure compound that plays a crucial role as an intermediate in organic synthesis, particularly in the preparation of chiral molecules. This compound belongs to the class of glycidyl esters, characterized by the presence of an epoxide functional group, which is highly reactive and useful in various chemical reactions. The (R)-configuration of glycidyl butyrate refers to its specific stereochemistry, which is important for applications where chirality is required to produce enantiomerically pure products.

The discovery of (R)-glycidyl butyrate can be traced back to advances in asymmetric synthesis, a field dedicated to producing molecules with specific three-dimensional arrangements. The development of efficient methods to synthesize enantiomerically pure epoxides like (R)-glycidyl butyrate has been driven by the increasing demand for chiral intermediates in the pharmaceutical, agrochemical, and fine chemical industries. The ability to control the stereochemistry of such compounds is critical in ensuring the efficacy and safety of biologically active molecules.

(R)-Glycidyl butyrate has a structure consisting of an epoxide ring attached to a butyrate ester group. The reactivity of the epoxide group makes this compound valuable for a wide range of chemical transformations. One of its primary uses is in the synthesis of chiral alcohols and diols, which are important intermediates in the production of pharmaceuticals. For example, (R)-glycidyl butyrate can undergo ring-opening reactions with nucleophiles, leading to the formation of chiral alcohols that are used in the synthesis of active pharmaceutical ingredients (APIs). The stereochemistry of the epoxide ensures that the resulting products have the desired three-dimensional structure, which is often crucial for the biological activity of the final compound.

In addition to its application in pharmaceutical synthesis, (R)-glycidyl butyrate is also used in the production of fine chemicals and materials. It can be incorporated into polymers, where the presence of the epoxide group allows for cross-linking and other modifications that enhance the properties of the material. Chiral glycidyl esters like (R)-glycidyl butyrate are particularly valuable in the production of optically active polymers, which have applications in areas such as liquid crystal displays (LCDs) and other advanced optical technologies.

Research has also explored the use of (R)-glycidyl butyrate in the field of asymmetric catalysis. Its highly reactive epoxide group can be used to create chiral environments that promote enantioselective reactions, enabling the synthesis of complex molecules with high stereochemical fidelity. This application is particularly relevant in the development of new drugs and agrochemicals, where the precise control of stereochemistry can significantly impact the effectiveness and safety of the final product.

The safety and environmental impact of (R)-glycidyl butyrate must also be considered, as the reactive nature of the epoxide group can pose certain hazards. Proper handling and storage procedures are necessary to prevent unwanted reactions and ensure safe use in industrial and laboratory settings. Moreover, efforts are being made to develop more sustainable methods for its synthesis, with a focus on reducing waste and improving the environmental profile of the production processes.

References

2018. Comparative features between recombinant lipases CALA-like from U. maydis and CALA from C. antarctica in thermal stability and selectivity. Biotechnology Letters, 40(12).
DOI: 10.1007/s10529-018-2630-4

2008. Resolution of (R,S)-(+/-)-glycidyl butyrate with immobilized Y-11 Trichosporon capitatum lipase in gelatin-containing microemulsion-based organogels. Colloids and surfaces. B, Biointerfaces, 66(2).
DOI: 10.1016/j.colsurfb.2008.08.011

2015. Enantioselective Kinetic Resolution of Esters of Chiral Primary Alcohols by Porcine Pancreatic Lipase. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-214-00121