gamma-Butyrolactone
[CAS# 96-48-0]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> FMOC-amino acid
• Name: gamma-Butyrolactone
• Synonyms: 4-Hydroxybutyric acid gamma-lactone; BLO; endo-cis-5-Norbornene-endo-2,3-dicarboxylic anhydride
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.09
• CAS Registry Number: 96-48-0
• EC Number: 202-509-5
• FEMA: 3291
• SMILES: C1CC(=O)OC1

Properties

• Density: 1.12
• Melting point: -45 °C
• Boiling point: 204-205 °C
• Refractive index: 1.4355-1.4375
• Flash point: 98 °C
• Water solubility: MISCIBLE

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H302-H315-H318-H319-H331-H336
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H336
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	2	H371

Discovery and Applications

Gamma-butyrolactone (GBL) is a versatile chemical compound with a range of industrial and commercial applications. Discovered in the early 20th century, GBL is a cyclic ester of gamma-hydroxybutyric acid (GHB) and has become widely used in various fields due to its unique chemical properties.

GBL was first synthesized in the 1920s as part of research into cyclic esters and their potential applications. Its discovery followed a series of studies aimed at developing compounds with useful chemical properties and reactivities. GBL quickly attracted attention for its ability to act as a solvent and reagent in organic synthesis, which laid the foundation for its widespread use in different industries.

In industrial settings, gamma-butyrolactone serves as an important solvent. It is used in the production of various chemicals and pharmaceuticals due to its ability to dissolve a wide range of substances. This makes it an essential component in the manufacture of resins, polymers, and coatings. GBL’s solvent properties also extend to applications in the electronics industry, where it is used in the cleaning of electronic components and circuit boards.

Another significant application of GBL is as a precursor in the synthesis of other chemicals. One of the most notable derivatives is gamma-hydroxybutyric acid (GHB), which is used in medical applications as an anesthetic and treatment for certain conditions. GBL is converted into GHB in the body, which underscores its importance in pharmaceutical research and development.

GBL is also employed in the agricultural sector as a component of various formulations. It is used in the production of herbicides and pesticides, where its properties help improve the effectiveness and stability of these products. Additionally, GBL is utilized in the formulation of cleaning agents and degreasers, where its ability to dissolve oils and fats enhances the cleaning process.

Despite its valuable applications, GBL has been subject to regulatory scrutiny due to its potential for misuse. It is known to have psychoactive effects similar to GHB, leading to concerns about its use as a recreational drug. As a result, its distribution and use are regulated in many countries to prevent abuse and ensure safety.

In summary, gamma-butyrolactone is a chemical compound with diverse industrial and commercial uses. Its solvent properties, role as a chemical precursor, and applications in agriculture and cleaning make it a valuable substance across various industries. However, its potential for misuse has led to regulatory measures to control its distribution and use.

References

2005. Nonbioluminescent Strains of Photobacterium phosphoreum Produce the Cell-to-Cell Communication Signal N-(3-Hydroxyoctanoyl)homoserine Lactone. Applied and Environmental Microbiology, 71(4).
DOI: 10.1128/aem.71.4.2113-2120.2005

2003. Total Synthesis of Cladocorans A and B: A Structural Revision. The Journal of Organic Chemistry, 68(7).
DOI: 10.1021/jo020743y

2003. Characterization of the Pharmacokinetic and Pharmacodynamic Interaction between Gamma-Hydroxybutyrate and Ethanol in the Rat. Toxicological sciences : an official journal of the Society of Toxicology, 73(2).
DOI: 10.1093/toxsci/kfg079