Compound: gamma-Valerolactone
SMILES: O=C1OC(C)CC1
InChIKey: GAEKPEKOJKCEMS-UHFFFAOYSA-N
Synonyms: gamma-Valerolactone, 108-29-2, 4-Pentanolide, 4-Valerolactone, gamma-Pentalactone, 4-Hydroxypentanoic acid lactone, 4-Hydroxyvaleric acid lactone, 2(3H)-Furanone, dihydro-5-methyl-, 4-Methyl-gamma-butyrolactone, gamma-Methyl-gamma-butyrolactone, 4-Methyl-4-hydroxybutanoic acid lactone, DIHYDRO-5-METHYL-2(3H)-FURANONE, 5-Methyltetrahydro-2-furanone, FEMA No. 3103, DTXSID0047618, 5-Methyldihydro-2(3H)-furanone, Valeric acid, 4-hydroxy-, gamma-lactone, Pentanoic acid, 4-hydroxy-, gamma-lactone, O7056XK37X, Dihydro-5-methylfuran-2(3H)-one, NSC-33700, DTXCID8027618, CHEBI:48569, RefChem:639610, (RS)-GAMMA-PENTALACTONE, 4-HYDROXYPENTANOIC ACID GAMMA-LACTONE, 203-569-5, 5-methyldihydrofuran-2(3H)-one, 5-methyloxolan-2-one, NSC 33700, .gamma.-Valerolactone, 5-methyltetrahydrofuran-2-one, y-Valerolactone, 2(3H)-Furanone, dihydr-5-methyl-, .gamma.-Methyl-.gamma.-butyrolactone, MFCD00005400, gamma-Pentanolactone, .gamma.-Pentalactone, g-valerolactone, CHEMBL195593, 4-Methyl-.gamma.-butyrolactone, Valeric acid, 4-hydroxy-, .gamma.-lactone, Pentanoic acid, 4-hydroxy-, .gamma.-lactone, Pentanolide-1,4, gamma-Valeryllactone, gamma-Valerolakton, gamma-Valerolakton [Czech], CCRIS 3597, EINECS 203-569-5, BRN 0080420, UNII-O7056XK37X, AI3-04327, |_-Valerolactone, gamma -Valerolactone, .gamma.-Valerolakton, .gamma.-Pentanolactone, 4-Methyl-g-butyrolactone, SCHEMBL37255, SCHEMBL71648, Dihydro-5-methyl-2-furanone, 5-17-09-00024 (Beilstein Handbook Reference), 57129-69-8, SCHEMBL124628, 5-methyl-dihydro-furan-2-one, orb3024925, orb3030288, SCHEMBL2039683, SCHEMBL2045075, GTPL13648, Pentanoic acid, .gamma.-lactone, GAMMA-VALEROLACTONE [FCC], (.+/-.)-4-Methylbutyrolactone, (.+/-.)-.gamma.-Valerolactone, (RS)-.GAMMA.-PENTALACTONE, Fr14083, NSC33700, 5-Methyldihydro-2(3H)-furanone #, dihydro-5-methyl-2(3H)-furanone,, Tox21_302624, BBL011475, BDBM50168010, EBC-03936, LMFA07040008, MSK014037, STL146587, .GAMMA.-VALEROLACTONE [FHFI], AKOS005206963, CS-W016654, DS-4944, FV04206, HY-W015938, gamma-Valerolactone, analytical standard, gamma-Valerolactone, >=99%, FCC, FG, gamma-Valerolactone, natural, 95%, FG, NCGC00256671-01, BP-31066, CAS-108-29-2, SY011304, (+/-)-.GAMMA.-METHYLBUTYROLACTONE, DB-003681, gamma-Valerolactone, ReagentPlus(R), 99%, NS00013327, V0007, EN300-61318, 4-HYDROXYPENTANOIC ACID .GAMMA.-LACTONE, P20539, F243089, Q845530, 2(3H)-Furanone, dihydro-5-methyl-, (.+/-.)-, gamma-Valerolactone, Vetec(TM) reagent grade, 98%, F0001-0163, Z963595138, (R)-gamma-Methyl-gamma-butyrolactone;(R)-Dihydro-5-methyl-2(3H)-furanone, 219630-19-0
Theoretical properties:
molecular_formula: C5H8O2
molecular_weight: 100.12 g/mol
exact_mass: 100.052429494 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 7
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 405 to 406 °F at 760 mmHg (NTP, 1992)
melting_point: -24 °F (NTP, 1992)
density: 1.057 at 68 °F (NTP, 1992) - Denser than water; will sink
solubility: greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
flash_point: 178 °F (NTP, 1992)
vapor_pressure: 0.5 mmHg at 84 °F ; 3.5 mmHg at 124 °F; 11.5 mmHg at 163 °F (NTP, 1992)
Descriptions:
pubchem: Gamma-valerolactone is a butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane. It has a role as a flavouring agent and a human xenobiotic metabolite.
chebi: A butan-4-olide that is dihydrofuran-2(3<em>H</em>)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to <em>n</em>-hexane.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: γ-Valerolactone (GVL) or gamma-valerolactone is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones.  GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.
GVL behaves as a prodrug to γ-hydroxyvaleric acid (GHV), a drug with similar effects to those of γ-hydroxybutyric acid (GHB), albeit with less potency in comparison. Because GHB is controlled in many parts of the world, while GVL is not, GVL has gained popularity as a legal substitute for GHB.