γ-Valerolactone
Product Information
Molecular Formula
C5H8O2
Molecular Weight
100.12
Description
γ-Valerolactone is a naturally occurring chemical found in fruits and is frequently used as a food additive. It can be converted to liquid alkenes which can be used as transportation fuels.
IUPAC Name
5-methyloxolan-2-one
SMILES
CC1CCC(=O)O1
InChI
InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
InChI Key
GAEKPEKOJKCEMS-UHFFFAOYSA-N
Boiling Point
191.57 °C (EPI 4.0)
Melting Point
-31 °C
Flash Point
204.8 °CF
Purity
95%
Density
1.05 g/mL
Solubility
greater than or equal to 100 mg/mL at 72° F (NTP, 1992);miscible with alcohol, most fixed oils and water
Appearance
Colorless to slightly yellow liquid
Application
A metabolite of n-hexane; Used as flavoring agent or adjuvant; A constituent of crude polyligneous acid; Used in dye bathes (coupling agent), brake fluid, cutting oils, and as a solvent for adhesives, insecticides, and lacquers.
Storage
Store tightly sealed under inert gas in a cool, well-ventilated area.
Refractive Index
1.431 : 1.434 at 20 deg C
Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
LogP
0.71190
Vapor Pressure
0.235mmHg at 25°C
Computed Properties
XLogP3
0.6
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
100.052429494 g/mol
Monoisotopic Mass
100.052429494 g/mol
Topological Polar Surface Area
26.3Ų
Heavy Atom Count
7
Formal Charge
0
Complexity
88.1
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2015197481-A1 | Controlled discharge of an energy store using redox shuttle additives | 2014-06-27 |
| WO-2015192051-A1 | Prelithiation solutions for lithium-ion batteries | 2014-06-12 |
| US-2015333371-A1 | Lithium titanate oxide as negative electrode in li-ion cells | 2014-05-15 |
| US-2015325852-A1 | Structurally controlled deposition of silicon onto nanowires | 2014-05-12 |
| US-2015315333-A1 | Aromatic resins for underlayers | 2014-04-30 |
| WO-2015161952-A1 | Aqueous two-component coating compositions and coatings produced therefrom with high resistance to erosion | 2014-04-24 |
| US-2015301449-A1 | Photoacid generator, chemically amplified resist composition, and patterning process | 2014-04-22 |
| EP-2933012-A1 | Method for manufacturing porous fluoropolymer membrane | 2014-04-14 |
| WO-2015153666-A1 | Ground meat replicas | 2014-03-31 |
| EP-2924097-A2 | Method for Catalytic Conversion of Ketoacids and Hydrotreatment to Hydrocarbons | 2014-03-26 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22890968 | 2012-09-01 | Development of heterogeneous catalysts for the conversion of levulinic acid to γ-valerolactone | ChemSusChem |
| 22349589 | 2012-06-01 | Gamma butyrolactone (GBL) and gamma valerolactone (GVL): similarities and differences in their effects on the acoustic startle reflex and the conditioned enhancement of startle in the rat | Pharmacology, biochemistry, and behavior |
| 22507905 | 2012-06-01 | Production of aromatic hydrocarbons through catalytic pyrolysis of γ-valerolactone from biomass | Bioresource technology |
| 22137345 | 2012-01-01 | 5- and 6-membered (thio)lactones are prodrug type carbonic anhydrase inhibitors | Bioorganic & medicinal chemistry letters |
| 22105964 | 2011-12-16 | Conversion of biomass-derived levulinate and formate esters into γ-valerolactone over supported gold catalysts | ChemSusChem |
| 22005944 | 2011-11-28 | Liquid-phase catalytic transfer hydrogenation and cyclization of levulinic acid and its esters to γ-valerolactone over metal oxide catalysts | Chemical communications (Cambridge, England) |
| 21786816 | 2011-09-14 | Selective homogeneous hydrogenation of biogenic carboxylic acids with [Ru(TriPhos)H]+: a mechanistic study | Journal of the American Chemical Society |
| 21732502 | 2011-08-16 | Hydrogen-independent reductive transformation of carbohydrate biomass into γ-valerolactone and pyrrolidone derivatives with supported gold catalysts | Angewandte Chemie (International ed. in English) |
| 21535802 | 2011-04-01 | Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds | Journal of food science |
| 21394926 | 2011-03-21 | Reactive extraction of levulinate esters and conversion to γ-valerolactone for production of liquid fuels | ChemSusChem |
