Structure via PubChem · Public domain (PubChem)
butyrolactone
Sign in to saveAlso known as 2-oxolanone, 4-butanolide, gamma-butyrolactone, tetrahydrofuran-2-one, 1,4-Lactone, oxolan-2-one, 2-Oxotetrahydrofuran, 1-Oxacyclopentan-2-one
γ-Butyrolactone (GBL) or '''gamma-butyrolactone''' is an organic compound with the formula . It is a hygroscopic, colorless, water-miscible liquid with a pleasant odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.
Chemical data
- Formula
- C4H6O2
- Molecular weight
- 86.09 g/mol
- IUPAC name
- oxolan-2-one
- SMILES
- C1CC(=O)OC1
- InChIKey
- YEJRWHAVMIAJKC-UHFFFAOYSA-N
- XLogP
- -0.6
- Polar surface area
- 26.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
7,714 papers- Butyrolactone signalling circuits for synthetic biology.Current opinion in chemical biology · 2015
- beta-Butyrolactone.IARC monographs on the evaluation of carcinogenic risks to humans · 1999
- Lichen butyrolactone derivatives disrupt oral bacterial membrane.Fitoterapia · 2019
- Synthesis of Gamma-Butyrolactone Hormones Enables Understanding of Natural Product Induction.ACS chemical biology · 2023
- Regulatory and evolutionary roles of pseudo γ-butyrolactone receptors in antibiotic biosynthesis and resistance.Applied microbiology and biotechnology · 2019
via PubMed
Wikidata facts
Show 6 more facts
- Commons category
- Gamma-Butyrolactone
- chemical formula
- C₄H₆O₂
- canonical SMILES
- C1CC(=O)OC1
- melting point
- -43.37
- electric dipole moment
- 4.27
- boiling point
- 204
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~12 min read
Encyclopedic overview
16 sectionsContents
- Occurrence
- Production and synthesis
- Reactions
- Polymerization
- Uses
- Pharmacology
- Pharmacokinetics
- Nutritional supplement
- Recreational drug
- Dangers
- Addictiveness and dependence
- Dose
- Legal status
- See also
- References
- External links
γ-Butyrolactone (GBL) or '''gamma-butyrolactone' is an organic compound with the formula . It is a hygroscopic, colorless, water-miscible liquid with a pleasant odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.
In humans, GBL acts as a prodrug for gamma-hydroxybutyric acid (GHB) and is often used as a recreational drug. GHB acts as a central nervous system (CNS) depressant with effects similar to those of barbiturates.
Excerpted from Wikipedia’s “butyrolactone” article, available under the CC BY-SA 4.0 licence.