Description
γ-Valerolactone (Item No. 28240) is an analytical reference standard categorized as a prodrug form of γ-hydroxyvaleric acid (GHV; ). This product is intended for research and forensic applications.
Chemical Properties
γ-Valerolactone has a sweet, herbaceous odor.
Chemical Properties
Colorless liquid. Surface
tension 30 dynes/cm (25C), viscosity 2.18 cP
(25C), pH (anhydrous): 7. pH (10% solution in distilled
water): 4.2. Miscible with water and most
organic solvents, resins, waxes, etc.; slightly misciblewith
zein, beeswax, petrolatum; immiscible with anhydrous glycerin, glue, casein, arabic gum, and
soybean protein. Combustible.
Occurrence
Reported found in boiled beef, beef fat, beer, cacao, Swiss cheese, ground and roasted coffee, roasted filberts,
milk fat, dried mushroom, peach, roasted peanuts, heated pork fat, black tea and yogurt. Also reported found in peach, strawberry
jam, tomato, wheaten bread, Gruyere cheese, heated butter, cooked beef, white wine, red wine, coffee and Bourbon vanilla.
Uses
It finds it application as a food additive that is used to improve the taste or odor of a food. It is also used as toiletry fragrances.
Uses
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. γ-Valerolactone is widely used in dye baths (coupling agent), brake fluids, cutting
oils, and as solvent for adhesives, insecticides, and
lacquers.
Uses
γ-valerolactone(GVL) can be used as a green solvent:
- To transform lignocellulose into furfural using a solid acid catalyst, H-mordenite.
- To synthesize phosphatidylserine.
Definition
ChEBI: 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.
Preparation
By reduction of levulinic acid followed by cyclization.
General Description
γ-Valerolactone(GVL) is a dipolar aprotic, bio-based, fully degradable, non-toxic green solvent and has been aligned with "Safer Solvent and Auxiliaries"," Use of Renewable Feedstocks and Design for Degradation".
General Description
γ-Valerolactone has been identified as one of the volatile flavor constituents in mango and honey.
Reactivity Profile
gamma-Valerolactone is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. gamma-Valerolactone is incompatible with strong oxidizers. . gamma-Valerolactone is incompatible with strong oxidizing agents. gamma-Valerolactone is also incompatible with strong acids, strong bases and strong reducing agents. .
Biochem/physiol Actions
Odor at 1%
Safety Profile
Moderately toxic by
ingestion. A skin irritant. Mutation data
reported. Combustible liquid when exposed
to heat or flame; can react with oxidizing
materials. To fight fire, use water, foam,
CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Purification Methods
Purify the -lactone by repeated fractional distillation [Boorman & Linstead J Chem Soc 577, 580 1933]. IR: max 1790 (CS2), 1775 (CHCl3) cm-1 [Jones et al. Can J Chem 3 7 2007 1959]. The BF3-complex distils at 110-111o/20mm [Reppe et al. Justus Liebigs Ann Chem 596 179 1955]. It is characterized by conversion to -hydroxy-n-valeramide on treatment with NH3, m 51.5-52o (by slow evaporation of a CHCl3 solution). [Beilstein 17 H 235, 17 I 131, 17 II 288, 17 III/IV 4176, 17/9 V 24.]
References
[1] H ANDRESEN-STREICHERT. Uptake of gamma-valerolactone–detection of gamma-hydroxyvaleric acid in human urine samples.[J]. Journal of analytical toxicology, 2013, 37 4: 250-254. DOI:
10.1093/jat/bkt013
