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W310311

Sigma-Aldrich

γ-Valerolactone

natural, ≥95%, FG

Synonym(s):

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:
108-29-2
Molecular Weight:
100.12
FEMA Number:
3103
Beilstein/REAXYS Number:
80420
EC Number:
203-569-5
Council of Europe no.:
757
MDL number:
MFCD00005400
UNSPSC Code:
12164502
PubChem Substance ID:
329830564
Flavis number:
10.013
NACRES:
NA.21

grade

FG
Kosher
natural

Quality Level

300

reg. compliance

EU Regulation 1334/2008 & 178/2002

vapor density

3.45 (vs air)

assay

≥95%

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.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

cocoa; herbaceous; woody; sweet; warm

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

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General description

γ-Valerolactone has been identified as one of the volatile flavor constituents in mango and honey.
Natural occurence: Barley, beef, beer, Swiss cheese, coffee, cocoa, mango, milk, mushroom, peach, pork, tea, soy and tomato

Application

The sweet, creamy notes of this lactone will enhance coconut, vanilla, caramel, toffee, milk chocolate, and the sweeter dairy flavors like cajeta, milk and whipped cream. Dried fruit flavors like date and fig, and nut flavors like almond and peanut butter are also good destinations for this material.

Biochem/physiol Actions

Odor at 1%
Taste at 8-15ppm

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

204.8 °F - closed cup

flash_point_c

96 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Organoleptic Characteristics of Flavor Materials
Michalski, J.
Perfumer & Flavorist, 39(5), 54-54 (2014)
Importance of some lactones and 2, 5-dimethyl-4-hydroxy-3 (2H)-furanone to mango (Mangifera indica L.) aroma.
Wilson III CW, et al.
Journal of Agricultural and Food Chemistry, 38(7), 1556-1559 (1990)
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;
Sys Stybe Johansen et al.
Journal of analytical toxicology, 35(1), 8-14 (2011-01-12)
A simple liquid chromatography-tandem mass spectrometry (LC-MS-MS) method has been developed and validated for simultaneous identification and quantification of γ-hydroxybutyrate (GHB), γ-butyrolactone (GBL), 1.4-butanediol (1.4-BD), and γ-valerolactone (GVL) in whole blood from forensic cases. The sample preparation of whole blood
Akiko Takagaki et al.
Bioscience, biotechnology, and biochemistry, 75(3), 582-585 (2011-03-11)
The antioxidative activities of (-)-epigallocatechin gallate (EGCg) metabolites degraded by rat intestinal flora were investigated by a flow injection analysis coupled to an on-line antioxidant detection system with the 2,2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation. All of the metabolites were
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