Page 81 - Zbornik_Konf_2019

https://doi.org/10.15414/2019.9788055220703

4 International Scientific Conference Abstracts Book
th
ISOMERS OF ESSENTIAL OILS COMPONENTS AND THEIR OPTICAL CHARACTERISTICS

Nataliia Frolova , Nataliia Yushchenko , Olga Korablova 2
1
1
1 National University of Food Technologies, Kyiv, Ukraine; E-mail.: frolovan809@gmail.com
2 M.M. Gryshko National Botanical Garden of National Academy of the Sciences of Ukraine,
Kyiv, Ukraine

In recent years in the world, a comprehensive study of optical isomers (enantiomers) of
organic compounds has been carried out. The main reason for this interest is due to the
important role that optical isomers play in the functioning of living systems and
manifestations of biological activity. The physicians have proved that differences in the
biological effects of optical isomers on the human body are due to different recognition of
them at the molecular level. Among the volatile plant substances that make up the smell of
plants, there are many examples of these biological manifestations, since odor recognition
also occurs at the molecular level.
Optical isomerism plays an exclusive role in the technologies of the processing of
essential oils since the enantiomers of one substance usually differ greatly in their flavor
tonality and strength. In particular, d (R) – Carvone has a fortifying odor, while l (S) – Carvone
– a smell of mint.
In essential oils, one of the forms of enantiomers predominates most often. It is proved
that d (R) – limonene predominates in essential oils of orange, lemon, mandarin, lime,
grapefruit, bergamot, cumin, dill, fennel, parsley. At the same time, l (S) – limonene is found in
essential oils of conifers, fir, stellate anise, peppermint. The value of optical activity may not
be large. However, according to this information, you can check the naturalness of essential
oils.
It should be noted that so far not all enantiomers of essential oils have been identified,
the structure of a number of substances has been sorted out relatively recently, and their
characteristics, including aromaticity, even have opposite meanings in the literature.
The subject of research was the optical isomers of Carvone, which was obtained by
adapted preparative method from Dill (Anethum graveolens L.), Cumin (Carum carvi L.) and
Mint (Mentha spicata) essential oils. We have been established their belonging to “dR – (+)” or
“lS – (-)” of the optical series, determined the value of the angle of rotation, and also
performed sensory analysis. The maximum isolation and collection of Carvone enantiomers
were provided by a high-performance preparative self-produced column.
The composition purity of the selected enantiomers was verified by gas-solid
chromatography on a self-made chromatographic column 3500 mm long, 3 mm in diameter,
HP – D-mannitol, solid support – W 80–100 mesh chromosorb (1.5–2.0 m).
According to our data, d (R) – Carvone (right-rotating form) is included in the
composition of Dill and Cumin, with a specific rotation of the plane of polarization [α] D +
62.5+0.05; [Α] D + 61+0.03. Essential oil of Mentha spicata contains l (S) – carvone (left-
rotating form) with a specific rotation of the [α] D polarization plane – 63.2+0.05.
The reliably several of the aromatic characteristics of Carvone enantiomers was
determined by organoleptic analysis. So: d (R) (+) – Carvone dill, has a spicy aroma of fresh
dill, d (R) (+) cumin has a sharp cumin flavor. l (S) – Carvone mint Mentha spicata has a mild
spicy aroma with a mint shade.
Keywords: essential oils composition, enantiomers, aromatic characteristics.

4 International Scientific Conference Agrobiodiversity Nutrition, Health and Quality of Human and Bees Life |81
th
September 11–13, 2019