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(Carum Carvi (Anethum Graveolens (Mentha Spicata Mentha Longifolia
(Carum Carvi (Anethum Graveolens (Mentha Spicata Mentha Longifolia
2, 95-97 (1987)
Optically pure (S)-( +)-carvone was isolated from the essential oils of the fruits of caraway and dill. Optically pure
(R)-(-)-carvone was isolated from the essential oils of the leaves of spearmint and Menfha longifolia.
Determination of the enantiomeric purity of the natural flavour was performed by 'H-NMR spectroscopy using a
chiral lanthanide shift reagent, Eu(hfc)3.
KEY WORDS (S)-( +)-Carvone (R)-(-)-Carvone Carum carvi L. Anelhum graveolens L. Mentha spicata
L. Mentha longifolia (L.) Huds. 'H-NMR Chiral Eu(hfc)3.
INTRODUCTION EXPERIMENTAL
PI. 8 7 6 5 4 3 2
obtained from R. C. Treatt and Co. ([a];'
-59.1'; c = 3.50. EtOH). Tris (3- Fig. I . ' H - N M R spectra of (S)-(+)-carvonc with Eu(hfc)l iit
(heptafluoropropylhydroxymethy1ene)-( )- + [LI/[S] = 0.7-0.8
camphorate], europium ( I l l ) [ E u ( h f ~ ) ~ ]was
,
obtained from Aldrich Chemical Co. Optical
rotations were measured on a Perkin-Elmer
Model 531 polarimeter. 'H-NMR spectra were
obtained at 200MHz with a Bruker Model
WP-2OOSY Fourier transform spectrometer. Car-
vone (lOpl) w a s dissolved in a solution of 2%
TMS in deuterochloroform (350 pl) in the NMR
tube. Ten-milligram aliquots of Eu(hfc)? were
added and dissolved in the solution. Molar ratios
of the lanthanide shift reagent to substrate
([L]/[S]) were 0.45, 0.60, 0.75, 0.90, 1.05 and
1.20.
I I . 7
~
An 6 5
i, 4 3
Fig. 3. 'H-NMR spectra of (RS)-carvone with Eu(hfc), at
[L]/[S] = 0.7-0.8
tion of the integrity of the chiral centre. Routine
detection of the enantiomeric purity of this
important nature identical flavour by 'H-NMR
using Eu(hfc)3 is a simple, fast and accurate
technique.