Compound: gamma-Butyrolactone
SMILES: O=C1OCCC1
InChIKey: YEJRWHAVMIAJKC-UHFFFAOYSA-N
Synonyms: gamma-Butyrolactone, BUTYROLACTONE, 96-48-0, dihydrofuran-2(3H)-one, 4-Butyrolactone, 4-Butanolide, 1,4-Butanolide, 4-Hydroxybutyric acid lactone, 2-Oxolanone, Dihydro-2(3H)-furanone, oxolan-2-one, Butyryl lactone, Butyrylactone, 4-Deoxytetronic acid, 1,2-Butanolide, Butyric acid lactone, BLON, gamma-BL, 2(3H)-Furanone, dihydro-, Tetrahydro-2-furanone, 4-Hydroxybutanoic acid lactone, gamma-Hydroxybutyric acid lactone, Dihydro-2-furanone, 1,4-Lactone, Agrisynth BLO, gamma-6480, 2-Oxotetrahydrofuran, gamma-Hydroxybutyrolactone, No Go, gamma-Butalactone, 1-Oxacyclopentan-2-one, FEMA No. 3291, Paint Clean G, gamma-Butyryllactone, gamma-Hydroxybutyric Acid cyclic ester, DTXSID6020224, OL659KIY4X, 4 Hydroxybutyric Acid Lactone, 4,5-Dihydro-2(3H)-furanone, Butanoic acid, 4-hydroxy-, gamma-lactone, NSC-4592, NIH 10540, DTXCID80224, CHEBI:42639, 2,3,4,5-Tetrahydro-2-furanone, LBG 11785, 4 Butyrolactone, 1,4 Butanolide, Furanone, tetrahydro 2, Furanone, tetrahydro-2-, Lactone, 4-Hydroxybutyric Acid, RefChem:922037, 202-509-5, 3-Hydroxybutyric acid lactone, g-Butyrolactone, tetrahydrofuran-2-one, gamma Butyrolactone, .gamma.-Butyrolactone, NCI-C55878, GBL, NSC 4592, gamma-Butanolactone, 1,4-Butyrolactone, .gamma.-BL, Butyric acid, 4-hydroxy-, gamma-lactone, BLO, .gamma.-6480, gamma-Butyrolactone-13C4, .gamma.-Hydroxybutyrolactone, .gamma.-Hydroxybutyric acid lactone, Butyrolactone-d6, MFCD00005386, 4-Hydroxybutyric acid, .gamma.-lactone, .gamma.-Hydroxybutyric acid cyclic ester, 4-Hydroxybutanoic acid, .gamma.-lactone, Gammabutyrolactone (GBL), 31213-03-3, Caswell No. 132B, gamma-butyrolacton, CAS-96-48-0, gamma-Butyrolactone (natural), CCRIS 2924, HSDB 4290, EINECS 202-509-5, UNII-OL659KIY4X, EPA Pesticide Chemical Code 122303, Revivarant, Remforce, g-Butalactone, 4-butanolactone, AI3-28121, g-Butyryllactone, GH Revitalizer, Blue Nitro, gammabutyrolactone, tetrahydrofuranone, 4-Deoxytetronate, C-1070, Dihyro-2-furanone, dihydrofuran-2-one, gamma-butyro-lactone, dihydro-furan-2-one, .alpha.-Butyrolactone, .gamma.-Butanolactone, 2(3H)-dihydrofuranone, 1-Oxacyclopentane-2-one, WLN: T5OVTJ, BUTYROLACTONE [MI], EC 202-509-5, SCHEMBL13481, SCHEMBL55741, SCHEMBL74653, BUTYROLACTONE [VANDF], Dynasolve 699 (Salt/Mix), g-Hydroxybutyric acid lactone, CHEMBL95681, SCHEMBL503156, SCHEMBL525156, Dihydro-(3 H)-furan-2-one, Butyric acid, .gamma.-lactone, BUTYROLACTONE [WHO-DD], GTPL5462, SCHEMBL1941687, SCHEMBL2015040, SCHEMBL8026571, SCHEMBL9421121, Butanoic acid, .gamma.-lactone, SCHEMBL25373276, GAMMA-BUTYROLACTONE [FCC], NSC4592, 4-hydroxy-Butanoic acid g-lactone, GAMMA-BUTYROLACTONE [HSDB], GAMMA-BUTYROLACTONE [IARC], CDA56865, Gamma-Lactone 4-hydroxybutyric acid, YIB48692, ZYB44194, .gamma.-Hydrooxybutyric acid lactone, gamma-Butyrolactone, >=99% (GC), Tox21_200490, Tox21_300188, Gamma-Lactone 4-hydroxy-butyric acid, Gamma-Lactone 4-hydroxybutanoic acid, LMFA07040004, STL281877, .GAMMA.-BUTYROLACTONE [FHFI], AKOS000119924, Gamma-Lactone 4-hydroxy-butanoic acid, DB04699, FB03390, gamma-Butyrolactone, analytical standard, NCGC00247920-01, NCGC00247920-02, NCGC00253913-01, NCGC00258044-01, Butyric acid, 4-hydroxy-, .gamma.-lactone, B0767, Butanoic acid, 4-hydroxy-, .gamma.-lactone, gamma-Butyrolactone; GBL; Gammabutyrolactone, NS00003450, gamma-Butyrolactone, ReagentPlus(R), >=99%, C01770, gamma-Butyrolactone, puriss., >=99.0% (GC), Q79739, gamma-Butyrolactone, SAJ first grade, >=99.5%, 4-Hydroxybutanoic acid lactone, >=98%, FCC, FG, GBL (gamma-Butyrolactone), 10mg/ml in Acetonitrile, GBL (gamma-Butyrolactone), 1mg/ml in Acetonitrile, GBL (gamma-Butyrolactone), 50mg/ml in Acetonitrile, gamma-Butyrolactone (GBL) 1.0 mg/ml in Acetonitrile, GBL (gamma-Butyrolactone), 100mg/ml in Acetonitrile, InChI=1/C4H6O2/c5-4-2-1-3-6-4/h1-3H, BUTANOIC ACID,4-HYDROXY,LACTONE   GAMMA-BUTYROLACTONE, BL
Theoretical properties:
molecular_formula: C4H6O2
molecular_weight: 86.09 g/mol
exact_mass: 86.036779430 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 6
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Oily liquid
color: Oily liquid
odor: Pleasant odor
boiling_point: 399 to 401 °F at 760 mmHg (NTP, 1992)
melting_point: -49 °F (NTP, 1992)
density: 1.1286 at 59 °F (NTP, 1992) - Denser than water; will sink
solubility: greater than or equal to 100 mg/mL at 55 °F (NTP, 1992)
flash_point: 209 °F (NTP, 1992)
vapor_pressure: less than 1 mmHg at 77 °F (NTP, 1992)
Descriptions:
pubchem: Gamma-butyrolactone is a butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2. It has a role as a metabolite and a neurotoxin.
chebi: A  butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.
chembl: BUTYROLACTONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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 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.