γ-Valerolactone
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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.
Quick Facts Names, Identifiers ...
Names | |
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IUPAC name
5-Methyloxolan-2-one | |
Other names
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Identifiers | |
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3D model (JSmol) |
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80420 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.003.245 |
EC Number |
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PubChem CID |
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UNII | |
UN number | 1224 |
CompTox Dashboard (EPA) |
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Properties | |
C5H8O2 | |
Molar mass | 100.116 |
Appearance | colorless liquid |
Density | 1.0546 g/mL (20 °C) [2] |
Melting point | −31 °C (−24 °F; 242 K) |
Boiling point | 205 °C (401 °F; 478 K)[2] |
>=100 mg/mL | |
Refractive index (nD) |
1.4333 (20 °C) [2] |
Thermochemistry | |
Std enthalpy of formation (ΔfH⦵298) |
-461.3 kJ·mol−1 |
Std enthalpy of combustion (ΔcH⦵298) |
-2649.6 kJ·mol−1 |
Hazards[3] | |
GHS labelling: | |
Warning | |
H319 | |
NFPA 704 (fire diamond) | |
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).
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Close
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.[4] Because GHB is controlled in many parts of the world, while GVL is not, GVL has gained popularity as a legal substitute for GHB.[4][5]