Γ-Valerolactone

γ-Valerolactone
Names
	IUPAC name 5-Methyloxolan-2-one
	Other names 5-Methyldihydrofuran-2(3H)-one,; 4-Pentanolide,; 4-Valerolactone,; 4-Pentalactone,; 4-Hydroxypentanoic acid lactone;
Identifiers
CAS Number	108-29-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	80420
ChEBI	CHEBI:48569 ;
ChEMBL	ChEMBL195593 ;
ChemSpider	7633 ;
ECHA InfoCard	100.003.245
EC Number	203-569-5;
PubChem CID	7921;
UNII	O7056XK37X ;
UN number	1224
CompTox Dashboard (EPA)	DTXSID0047618 ;
	InChI InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3 Key: GAEKPEKOJKCEMS-UHFFFAOYSA-N ; InChI=1/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3 Key: GAEKPEKOJKCEMS-UHFFFAOYAX;
	SMILES CC1CCC(=O)O1;
Properties
Chemical formula	C5H8O2
Molar mass	100.116
Appearance	colorless liquid
Density	1.0546 g/mL (20 °C)
Melting point	−31 °C (−24 °F; 242 K)
Boiling point	205 °C (401 °F; 478 K)
Solubility in water	>=100 mg/mL
Refractive index (nD)	1.4333 (20 °C)
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−461.3 kJ·mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2649.6 kJ·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
NFPA 704 (fire diamond)	2 2 0
Flash point	81 °C (178 °F; 354 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.