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
Canonical 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
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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