General Description
Clear, colorless, mobile liquid. pH (anhydrous): 7.0. pH (10% solution in distilled water): 4.2.
Reactivity Profile
GAMMA-VALEROLACTONE(108-29-2) 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. This chemical is incompatible with strong oxidizers. . This chemical is incompatible with strong oxidizing agents. GAMMA-VALEROLACTONE(108-29-2) is also incompatible with strong acids, strong bases and strong reducing agents. .
Air & Water Reactions
Water soluble.
Fire Hazard
This chemical is combustible.
Description
γ-Valerolactone (Item No. 28240) is an analytical reference standard categorized as a prodrug form of γ-hydroxyvaleric acid (GHV; Item No.
28241).
1 This product is intended for research and forensic applications.
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.
Chemical Properties
γ-Valerolactone has a sweet, herbaceous odor.
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.
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.
Biochem/physiol Actions
Odor at 1%
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.]
