γ-Valerolactone Property

Melting point:

−31 °C(lit.)

Boiling point:

207-208 °C(lit.)

Density 

1.05 g/mL at 25 °C(lit.)

vapor density 

3.45 (vs air)

vapor pressure 

30-44Pa at 20-25℃

refractive index 

n20/D 1.432(lit.)

FEMA 

3103 | GAMMA-VALEROLACTONE

Flash point:

204.8 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Liquid

color 

Clear colorless

Odor

at 100.00 %. herbal sweet warm tobacco cocoa woody

PH

7 (H2O, 20℃)

Odor Type

herbal

Water Solubility 

MISCIBLE

JECFA Number

220

BRN 

80420

Dielectric constant

36.140000000000001

InChIKey

GAEKPEKOJKCEMS-UHFFFAOYSA-N

LogP

-0.27

CAS DataBase Reference

108-29-2(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-Furanone, dihydro-5-methyl-(108-29-2)

EPA Substance Registry System

2(3H)-Furanone, dihydro-5-methyl- (108-29-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36-36/37/38

Safety Statements 

39-26-37/39

WGK Germany 

2

RTECS 

LU3580000

TSCA 

Yes

HS Code 

29322980

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

γ-Valerolactone Chemical Properties,Usage,Production

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

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.

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.

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.

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.

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 1286, 1990 DOI: 10.1021/ja00159a082
Tetrahedron Letters, 26, p. 5639, 1985 DOI: 10.1016/S0040-4039(01)80907-2
The Journal of Organic Chemistry, 50, p. 3930, 1985 DOI: 10.1021/jo00220a053

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.]