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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
Molecular Weight:
100.12
MDL Number:
MFCD00005400
MOL File:
108-29-2.mol
MSDS File:
SDS
Last updated:2024-03-11 13:16:07

γ-Valerolactone Properties

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
PH 7 (H2O, 20℃)
Odor at 100.00 %. herbal sweet warm tobacco cocoa woody
Odor Type herbal
Water Solubility MISCIBLE
JECFA Number 220
BRN 80420
Dielectric constant 36.140000000000001
InChIKey GAEKPEKOJKCEMS-UHFFFAOYSA-N
LogP -0.27
Substances Added to Food (formerly EAFUS) GAMMA-VALEROLACTONE
CAS DataBase Reference 108-29-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII O7056XK37X
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

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
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
NFPA 704
1
2 0

γ-Valerolactone price More Price(49)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W310311 γ-Valerolactone natural, 95%, FG 108-29-2 100g $148 2024-03-01 Buy
Sigma-Aldrich W310311 γ-Valerolactone natural, 95%, FG 108-29-2 500g $609 2024-03-01 Buy
Sigma-Aldrich W310311 γ-Valerolactone natural, 95%, FG 108-29-2 1kg $808 2024-03-01 Buy
Sigma-Aldrich W310301 γ-Valerolactone ≥99%, FCC, FG 108-29-2 1kg $161 2024-03-01 Buy
Sigma-Aldrich W310301 γ-Valerolactone ≥99%, FCC, FG 108-29-2 5kg $620 2024-03-01 Buy
Product number Packaging Price Buy
W310311 100g $148 Buy
W310311 500g $609 Buy
W310311 1kg $808 Buy
W310301 1kg $161 Buy
W310301 5kg $620 Buy

γ-Valerolactone Chemical Properties,Uses,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

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?(GVL) can be used as a green solvent:

  • To transform lignocellulose into furfural using a solid acid catalyst, H-mordenite.
  • To synthesize phosphatidylserine.

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 has been identified as one of the volatile flavor constituents in mango and honey.

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".

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.]

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View Lastest Price from γ-Valerolactone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
gamma-Valerolactone pictures 2024-03-28 gamma-Valerolactone
108-29-2
US $2.00 / kg 1kg ≥99% 500mt/year Jinan Finer Chemical Co., Ltd
γ-Valerolactone pictures 2024-03-28 γ-Valerolactone
108-29-2
US $25.00 / kg 1000kg 99% 1000kg/day Hebei Yime New Material Technology Co., Ltd.
γ-Valerolactone pictures 2024-03-11 γ-Valerolactone
108-29-2
US $20.00-5.00 / kg 500kg 99.9 200tons Shandong Juchuang Chemical Co., LTD
  • γ-Valerolactone pictures
  • γ-Valerolactone
    108-29-2
  • US $25.00 / kg
  • 99%
  • Hebei Yime New Material Technology Co., Ltd.
  • γ-Valerolactone pictures
  • γ-Valerolactone
    108-29-2
  • US $20.00-5.00 / kg
  • 99.9
  • Shandong Juchuang Chemical Co., LTD
4,5-DIHYDRO-5-METHYL-2 (3H)-FURANONE 4-HYDROXYPENTANOIC ACID LACTONE 4-HYDROXYVALERIC ACID G-LACTONE 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 5-Methyldihydro-2(3H)-furanone 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 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 GAMMA-PENTANOLACTONE GAMMA-METHYL-GAMMA-BUTYROLACTONE FEMA 3103 tetrahydro-α-pyrone γ-Valerolactone, 98+% 4-Hydroxyvaleric acid lactone 4-hydroxyvalericacidlactone 4-Methyl-gamma-butyrolactone 4-Valerolacetone δ-hydroxyvaleric acid lactone c-valerolactone dihydro-5-methyl-2(3h)-furanon gamma-Pentalactone gamma-Valerolakton -Methylbutyrolactone Pentanoic acid, 4-hydroxy-, gamma-lactone γ-Valerolactone VALEROLACTONE, GAMMA- 1,4-Valcrolactone 4,5-Dihydro-5-methyl-2(3H)-furanone~4-Hydroxypentanoic acid lactone~gamma-Pentanolactone (+/-)-GAMMA-VALEROLACTONE 98+% FCC GAMMA-VALEROLACTONE,DELTA-VALEROLACTONE GAMMA-VALERICLACTONE 4-METHYLBUTYROLACTONE 24R,25-Dihydroxy Fusidic Acid &delta 24S,25-Dihydroxy Fusidic Acid &delta D,L-Mevalonic Acid Lactone (D,L-b-Hydroxy-b-methyl-&part