CHEBI:42639 - γ-butyrolactone

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ChEBI Name γ-butyrolactone
ChEBI ID CHEBI:42639
ChEBI ASCII Name gamma-butyrolactone
Definition A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42636, CHEBI:18871
Supplier Information No supplier information found for this compound.
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γ-Butyrolactone (GBL) or gamma-butyrolactone is an organic compound with the formula O=CO(CH2)3. It is a hygroscopic, colorless, water-miscible liquid with a weak characteristic 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.
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Formula C4H6O2
Net Charge 0
Average Mass 86.08920
Monoisotopic Mass 86.03678
InChI InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
InChIKey YEJRWHAVMIAJKC-UHFFFAOYSA-N
SMILES O=C1CCCO1
Roles Classification
Biological Role(s): neurotoxin
A poison that interferes with the functions of the nervous system.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing γ-butyrolactone (CHEBI:42639) has role metabolite (CHEBI:25212)
γ-butyrolactone (CHEBI:42639) has role neurotoxin (CHEBI:50910)
γ-butyrolactone (CHEBI:42639) is a butan-4-olide (CHEBI:22950)
Incoming (3R,4R)-4-(hydroxymethyl)-3-(6-methylheptanoyl)oxolan-2-one (CHEBI:73982) has functional parent γ-butyrolactone (CHEBI:42639)
4-butyl-γ-butyrolactone (CHEBI:87416) has functional parent γ-butyrolactone (CHEBI:42639)
5-ethoxydihydro-2(3H)-furanone (CHEBI:87307) has functional parent γ-butyrolactone (CHEBI:42639)
podorhizol (CHEBI:37394) has functional parent γ-butyrolactone (CHEBI:42639)
IUPAC Name
dihydrofuran-2(3H)-one
Synonyms Sources
1,2-butanolide UM-BBD
1,4-Butanolide UM-BBD
1,4-Lactone KEGG COMPOUND
4-Butyrolactone UM-BBD
4-Deoxytetronic acid UM-BBD
4-Hydroxybutyric acid lactone UM-BBD
Butyrolactone UM-BBD
dihydro-2(3H)-furanone NIST Chemistry WebBook
γ-butanolactone NIST Chemistry WebBook
GAMMA-BUTYROLACTONE PDBeChem
γ-butyrolactone UniProt
γ-hydroxybutyric acid lactone NIST Chemistry WebBook
γ-hydroxybutyrolactone NIST Chemistry WebBook
tetrahydrofuran-2-one ChEBI
Manual Xrefs Databases
c0033 UM-BBD
C01770 KEGG COMPOUND
DB04699 DrugBank
Gamma-Butyrolactone Wikipedia
GBL PDBeChem
HMDB0000549 HMDB
View more database links
Registry Numbers Types Sources
105248 Reaxys Registry Number Reaxys
96-48-0 CAS Registry Number ChemIDplus
96-48-0 CAS Registry Number NIST Chemistry WebBook
Citations
Ingels AS, Wille SM, Samyn N, Lambert WE, Stove CP (2014)
Screening and confirmation methods for GHB determination in biological fluids.
Analytical and bioanalytical chemistry 406, 3553-3577 [PubMed:24500753]
[show Abstract]
Rosi L, Frediani P, Bartolucci G (2013)
Determination of GHB and its precursors (GBL and 1,4-BD) in dietary supplements through the synthesis of their isotopologues and analysis by GC-MS method.
Journal of pharmaceutical and biomedical analysis 74, 31-38 [PubMed:23245230]
[show Abstract]
Sax JK, Dash BC, Hong R, Dicker DT, El-Deiry WS (2002)
The cyclin-dependent kinase inhibitor butyrolactone is a potent inhibitor of p21 (WAF1/CIP1 expression).
Cell cycle (Georgetown, Tex.) 1, 90-96 [PubMed:12429914]
[show Abstract]
Last Modified
23 October 2015