ChemicalBook > CAS DataBase List > γ-Valerolactone

γ-Valerolactone

Product Name
γ-Valerolactone
CAS No.
108-29-2
Chemical Name
γ-Valerolactone
Synonyms
5-Methyldihydrofuran-2(3H)-one;GAMMA-VALEROLACTONE;Dihydro-5-methyl-2(3H)-furanone;γ-Pentalactone;4-PENTANOLIDE;G-VALEROLACTONE;GAMMA-VALEROLACTONE NATURAL;2(3H)-Furanone,dihydro-5-methyl-;amma-VaL;FEMA 3103
CBNumber
CB4285373
Molecular Formula
C5H8O2
Formula Weight
100.12
MOL File
108-29-2.mol
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W310311
Product name
γ-Valerolactone
Purity
natural, 95%, FG
Packaging
100g
Price
$148
Updated
2024/03/01
Sigma-Aldrich
Product number
W310311
Product name
γ-Valerolactone
Purity
natural, 95%, FG
Packaging
500g
Price
$609
Updated
2024/03/01
Sigma-Aldrich
Product number
W310311
Product name
γ-Valerolactone
Purity
natural, 95%, FG
Packaging
1kg
Price
$808
Updated
2024/03/01
Sigma-Aldrich
Product number
W310301
Product name
γ-Valerolactone
Purity
≥99%, FCC, FG
Packaging
1kg
Price
$161
Updated
2024/03/01
Sigma-Aldrich
Product number
W310301
Product name
γ-Valerolactone
Purity
≥99%, FCC, FG
Packaging
5kg
Price
$620
Updated
2024/03/01
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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.]

γ-Valerolactone Preparation Products And Raw materials

Raw materials

Acetoxyacetic acid Levulinic acid Metal catalyst

Preparation Products

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View Lastest Price from γ-Valerolactone manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Y-Valerolactone 108-29-2
Price
US $75.00-20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-30
Shandong Deshang Chemical Co., Ltd.
Product
γ-Valerolactone 108-29-2
Price
US $8.80-3.50/kg
Min. Order
1kg
Purity
99%
Supply Ability
10 tons
Release date
2024-08-05
Shanghai UCHEM Inc.
Product
gamma-Valerolactone 108-29-2
Price
US $74.00/kg
Min. Order
1kg
Purity
0.98
Supply Ability
100kg
Release date
2023-11-16

108-29-2, γ-ValerolactoneRelated Search:

Pirimiphos-methyl TRIOXSALEN METSULFURON METHYL 4-Aminobutyric acid gamma-Decalactone Sodium 2-propylpentanoate 2-Oxetanone Methyl salicylate Methyl acetate Kresoxim-methyl Thiophanate-methyl Tribenuron methyl Spironolactone D-Glucurone D-(+)-Glucono-1,5-lactone ε-Caprolactone Methyl Parathion-methyl

  • GAMMA-VALEROLACTONE NATURAL
  • gamma-Valerolactone, 98+%
  • γ-Methyl-γ-butyrolactone, 4,5-Dihydro-5-methyl-2(3H)-furanone, 4-Hydroxypentanoic acid lactone
  • γ-Methyl-γ-butyrolactone, (±)-γ-Valerolactone, 4,5-Dihydro-5-methyl-2(3H)-furanone, 4-Hydroxypentanoic acid lactone
  • 4,5-Dihydro-5-methyl-2(3H)-franone
  • γ-Valeroactone
  • ^y-Valerolactone, 98+%
  • γ-Valerolactone >= 99.0%, Natural, FCC
  • Dihydro-5-methylfuran-2(3H)-one
  • gaMMa-Valerolactone, 98% 100ML
  • gaMMa-Valerolactone, 98% 5ML
  • GaMMa-ValerolaCLone
  • G-PENTANOLACTONE FOR SYNTHESIS
  • gaMMa-Valerolactone ReagentPlus(R), 99%
  • γ-Pentanolactone for synthesis
  • γ-Pentalactone
  • G-VALEROLACTONE
  • GAMMA-PENTANOLACTONE
  • GAMMA-METHYL-GAMMA-BUTYROLACTONE
  • GAMMA-VALEROLACTONE
  • FEMA 3103
  • 4,5-DIHYDRO-5-METHYL-2 (3H)-FURANONE
  • 4-HYDROXYPENTANOIC ACID LACTONE
  • 4-HYDROXYVALERIC ACID G-LACTONE
  • 4-PENTANOLIDE
  • 4-VALEROLACTONE
  • gamma-Valerolactone Vetec(TM) reagent grade, 98%
  • 1，4-Valerolactone
  • (±)-5-Methyl-dihydro-furan-2-one
  • (R,S)-5-Methyl-dihydro-furan-2-one
  • 2(3H)-Furanone,dihydro-5-methyl-
  • 5-Methyldihydro-2(3H)-furanone
  • 5-Methyldihydrofuran-2(3H)-one
  • 5-methyl-dihydro-furan-2-one
  • 5-Methyloxolan-2-one
  • 5-methyltetrahydro-2-furanone
  • 5-methyltetrahydrofuran-2-one
  • 2-METHYLBUTYROLACTONE
  • gamma-Valerolacton
  • VALEROLACTON GAMMA
  • tetrahydrocoumalin
  • tetrahydro-α-pyrone
  • γ-Valerolactone, 98+%
  • 4-Hydroxyvaleric acid lactone
  • 4-hydroxyvalericacidlactone
  • 4-Methyl-gamma-butyrolactone
  • 4-Valerolacetone
  • δ-hydroxyvaleric acid lactone
  • 24R,25-Dihydroxy Fusidic Acid &delta
  • 24S,25-Dihydroxy Fusidic Acid &delta
  • D,L-Mevalonic Acid Lactone (D,L-b-Hydroxy-b-methyl-&part
  • Pravastatin-d9 &delta
  • gamma-VALEROLACTONE FCC
  • γ-Valerolavtone
  • Gamma Pentanolide
  • amma-VaL
  • Gamma Valerolactone COA
  • 4,5-Dihydro-5-methyl-2(3H)-furanone msds