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V403

Sigma-Aldrich

γ-Valerolactone

ReagentPlus®, 99%

Synonym(s):

γ-Valerolactone, gamma-Valerolactone, γ-Methyl-γ-butyrolactone, 4,5-Dihydro-5-methyl-2(3H)-furanone, 4-Hydroxypentanoic acid lactone

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About This Item

Empirical Formula (Hill Notation):
C5H8O2
CAS Number:
Molecular Weight:
100.12
Beilstein:
80420
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.45 (vs air)

Quality Level

product line

ReagentPlus®

Assay

99%

refractive index

n20/D 1.432 (lit.)

bp

207-208 °C (lit.)
82-85 °C/10 mmHg (lit.)

mp

−31 °C (lit.)

density

1.05 g/mL at 25 °C (lit.)

SMILES string

CC1CCC(=O)O1

InChI

1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3

InChI key

GAEKPEKOJKCEMS-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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General description

γ-valerolactone (GVL) is found naturally in fruits and often used as a fuel additive and food ingredient. It is prominently employed in the production of both energy and carbon-based products.

Application

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

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γ-Valerolactone-a sustainable liquid for energy and carbon-based chemicals
Horvath I, et al.
Green Chemistry, 10(2), 238-242 (2008)
Highly efficient synthesis of phosphatidylserine in the eco-friendly solvent γ-valerolactone
Duan Z-Q and Hu Fei
Green Chemistry, 14(6), 1581-1583 (2012)
Jesse Q Bond et al.
Langmuir : the ACS journal of surfaces and colloids, 26(21), 16291-16298 (2010-06-02)
γ-Valerolactone (GVL) has been identified as a promising, sustainable platform molecule that can be produced from lignocellulosic biomass. The chemical flexibility of GVL has allowed the development of a variety of processes to prepare renewable fuels and chemicals. In the
Jean-Paul Lange et al.
Chemical communications (Cambridge, England), (33)(33), 3488-3490 (2007-08-19)
Methyl pentenoate, a promising Nylon intermediate, is produced in >95% yield via the transesterification of gamma-valerolactone, a bio-based intermediate, under catalytic distillation conditions.
Laureen J Marinetti et al.
Pharmacology, biochemistry, and behavior, 101(4), 602-608 (2012-02-22)
Gamma butyrolactone (GBL) is metabolized to gamma hydroxybutyrate (GHB) in the body. GHB is a DEA Schedule 1 compound; GBL is a DEA List 1 chemical. Gamma valerolactone (GVL) is the 4-methyl analog of GBL; GVL is metabolized to 4-methyl-GHB;

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