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77011

Sigma-Aldrich

(S)-γ-Caprolactone

≥98.5% (GC)

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Synonym(s):
(−)-γ-Hexalactone, (5S)-5-Ethyldihydro-2(3H)-furanone, (5S)-5-Ethyloxolan-2-one, (S)-γ-Ethyl-γ-butyrolactone, (S)-4-Hexanolide
CAS Number:
Beilstein:
41035-07-8
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

Assay

≥98.5% (GC)

form

liquid

optical activity

[α]20/D -51±1°, c = 1 in methanol

optical purity

enantiomeric excess: ≥95.0% (GC)

storage temp.

2-8°C

SMILES string

CC[C@H]1CCC(O1)=O

InChI

1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3/t5-/m0/s1

InChI key

JBFHTYHTHYHCDJ-YFKPBYRVSA-N

Biochem/physiol Actions

Metabolite produced by plants, as a component of aroma flavours and fragrances and aromas of fruits and vegetables. An intense aroma of caramel and liquorice, found in many fruits, but also in different foods and beverages, like butter, beer, brandy, tea, and added to tobacco as flavoring agent.
gamma-Caprolactone is occasionally found as a volatile component of human urine and has been found in the polar fraction of human blood. Biological fluids such as blood and urine have been shown to contain a large number of components apparently present in all individuals. It is a promotor of the growth of biocontrol bacteria and a metabolite of a new assimilative pathway.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

WGK

WGK 2

Flash Point(F)

No data available

Flash Point(C)

No data available


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Stereoisomeric flavor compounds: structure and properties of gamma-lactone enantiomers.
Mosandl, A. and Gunther, C.
Journal of Agricultural and Food Chemistry, 37, 413-418 (1989)
Carlo Bicchi et al.
Journal of chromatography. A, 1212(1-2), 114-123 (2008-10-31)
The analysis of complex real-world samples of vegetable origin requires rapid and accurate routine methods, enabling laboratories to increase sample throughput and productivity while reducing analysis costs. This study examines shortening enantioselective-GC (ES-GC) analysis time following the approaches used in

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