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.
In the Vinony graph
Within Vinony's link graph, butyrolactone is referenced by 525 other articles, and connects out to 4-hydroxybutyric acid, picrotoxin and tetrahydrodeoxycorticosterone.
Vinony files it under Chembox having GHS data, Chembox image size set and Designer prodrugs.
Its subject is documented across 25 Wikipedia language editions.
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
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
via Wikidata · CC0
~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.