This work presents a literature review on the biological activity of S-carvone, geraniol and deri... more This work presents a literature review on the biological activity of S-carvone, geraniol and derivatives of these compounds, which are formed in the process of isomerization (during the process of geraniol isomerization, oxidation products of this compound are also obtained). Moreover, this work presents preliminary microbiological tests of creams with the addition of these biologically active compounds: S-carvone, geraniol, carvacrol (an S-carvone isomerization product), nerol (a geraniol isomerization product), linalool (a geraniol isomerization product) and citral (a geraniol oxidation product). Because the post-reaction mixture obtained after the S-carvone isomerization has a relatively simple composition, it was also added to creams and tested without isolating pure compounds. This may be a cheaper alternative to creams prepared with the addition of pure compounds. The mixture obtained after the geraniol isomerization process has a very complex composition; therefore, only comp...
The isomerization of limonene over the Ti-SBA-15 catalyst, which was prepared by the hydrothermal... more The isomerization of limonene over the Ti-SBA-15 catalyst, which was prepared by the hydrothermal method, was studied. The main products of limonene isomerization were terpinolene, α-terpinene, γ-terpinene, and p-cymene—products with numerous applications. The amount of these products depended on reaction time, temperature, and catalyst content. These parameters changed in the following range: reaction time 30–1380 min, temperature 140–160 °C, and catalyst content 5–15 wt %. Finally, the most favorable conditions for the limonene isomerization process were established: a reaction time of 180 min, temperature of 160 °C, and amount of the catalyst 15 wt %. In order to obtain p-cymene (dehydroaromatization product), the most favorable conditions are similar but the reaction time should be 1380 min. The application of such conditions allowed us to obtain the highest amounts of the desired products in the shortest time.
The antimicrobial properties of natural limonene and the compounds obtained after isomerization o... more The antimicrobial properties of natural limonene and the compounds obtained after isomerization of limonene (α-terpinene, γ-terpinene, terpinolene, and p-cymene) were studied. The following microorganisms were selected for the tests: Gram-negative bacteria Escherichia coli K12 (ACCT 25922), Gram-positive Staphylococcus epidermidis (ACCT 49461), yeast fungi Candida albicans, and fungi Trichophyton rubrum, Aspergillus niger, Penicillium commune, Trichoderma viride, and Cladosporium cladosporioides. During the studies, terpinolene showed the highest activity, and therefore, this compound was chosen for the preparation of therapeutic creams (content of terpinolene: 0.5 and 2 wt%). The obtained creams were active in the microbiological tests even at the lowest content of terpinolene. The mixture of products obtained after the isomerization of limonene also showed antimicrobial activity. Probably, in the future, this mixture of products can be used as a potential and relatively inexpensiv...
This work presents studies on the activity of the Ti-SBA-16 (SBA—Santa Barbara Amorphous) catalys... more This work presents studies on the activity of the Ti-SBA-16 (SBA—Santa Barbara Amorphous) catalyst in the isomerization of limonene and S-carvone. The Ti-SBA-16 catalyst was synthesized by a two-step method: first, the SBA-16 material was produced, and then it was impregnated with the titanium source. The Ti-SBA-16 catalyst was subjected to detailed characterizations by means of instrumental methods: XRD (X-ray Diffraction), UV-Vis (Ultraviolet–Visible) spectroscopy, FTIR (Fourier-Transform Infrared) spectroscopy, SEM (Scanning Electron Microscopy) with EDX (Energy Dispersive X-ray) spectroscopy, and EDXRF (Energy Dispersive X-ray Fluorescence). Both limonene and S-carvone underwent isomerization over the Ti-SBA-16 catalyst. In the isomerization of limonene, the main product was terpinolene, and its highest yield amounted to 39 mol% after 300 min at 170 °C with a catalyst content of 15 wt%. Under these conditions, the conversion of limonene reached 78 mol%. In contrast, the highest ...
: The interest in biologically active compounds of natural origin has increased significantly rec... more : The interest in biologically active compounds of natural origin has increased significantly recently. Studies of scientists focuses on the activity of these compounds, as well as their modifications, which allow wide range of use in pharmacology. With the present knowledge and technologies, it is possible to obtain compounds with increased biological activity and targeted acting. Curcuminoids are the main components of turmeric (Curcuma longa L.), a plant from India and South-East Asia. Due to its intense yellow-orange color and pleasant aroma, the powdered rootstalk is widely used in food industry, as natural dye and spice. The chemical compound responsible for the characteristic color of rhizomes of curcuma is 1,6-heptadien-3,5-dione-1,7-bis(4-hydroxy-3-methoxyphenyl) - (1E, 6E) called curcumin. This work aims to characterize curcumin in terms of its structure, therapeutic properties and also as a substrate for the synthesis of valuable derivatives. Knowledge about this relationship based on literature analysis will enable a better understanding of the factors responsible for its biological activity.
ABSTRAKTWstęp: Limonen jest monoterpenem, który w przyrodzie występuje w formie dwóch izomerów R ... more ABSTRAKTWstęp: Limonen jest monoterpenem, który w przyrodzie występuje w formie dwóch izomerów R i S. Z tych dwóch izomerów szczególną uwagę zwraca się obecnie na R-(+)-limonen, głównie ze względu na łatwość jego pozyskania z tanich i odnawialnych surowców naturalnych (odpadowe skórki pomarańczy) oraz bardzo liczne i różnorodne zastosowania, m.in. w medycynie, kosmetyce i przemyśle perfumeryjnym.Materiały i metody: Artykuł jest pracą przeglądową, w której omówiono zastosowania limonenu, przy czym duży nacisk został położony na opisanie zastosowań tego związku w medycynie. Z danych literaturowych wynika, że limonen w wielu przypadkach wykazuje działanie lecznicze. W artykule zwrócono także uwagę na bezpieczeństwo stosowania limonenu, czego dowodem są opisywane w literaturze wyniki doświadczeń przeprowadzonych na ludziach i zwierzętach. Opisano również metabolizm limonenu w organizmie człowieka, a także badania nad alergizującym wpływem produktów utlenienia limonenu, zarówno izomeru S...
This work describes research on the isomerization of R(+)-limonene over the Ti-MCM-41 catalyst. T... more This work describes research on the isomerization of R(+)-limonene over the Ti-MCM-41 catalyst. The studies showed that the Ti-MCM-41 catalyst is an active catalyst in the isomerization of R(+)-limonene. As a result of the isomerization of this compound, it is possible to obtain α-terpinene, γ-terpinene, terpinolene and p-cymene. Terpinolene is the main product of this process, and p-cymene is formed by the alpha-terpinene, gamma-terpinene and terpinolene dehydrogenation. The aforementioned products are of great practical importance. The most favorable reaction conditions leading to the obtaining of limonene isomerization products is the use of the catalyst in an amount of 15 wt% and the temperature of 160 °C. Depending on whether the desired products are the isomers of limonene (γ-terpinene, α-terpinene and terpinolene) or the product of their dehydroaromatization (β-cymene), it is possible to shorten or extend the reaction time. The method for the isomerization of limonene on the ...
The isomerization of limonene over natural the zeolite, clinoptilolite, was studied. The main pro... more The isomerization of limonene over natural the zeolite, clinoptilolite, was studied. The main products of limonene isomerization were terpinolene, α-terpinene, γ-terpinene and p-cymene. These products have numerous applications in the cosmetic, food and pharmaceutical industries. The main parameters affecting limonene isomerization were reaction time, temperature and catalyst content. These parameters varied within the following ranges: reaction time 15–1440 min; temperature 155–175°C; and catalyst content 5–15 wt.%. Terpinolene was obtained after reaction for 60 min at 175°C using 10 wt.% catalyst. p-Cymene was produced using similar conditions as for terpinolene except for a longer reaction time of 1440 min. The use of optimum experimental conditions allowed the greatest amounts of the desired products to be obtained in the shortest time.
This work presents a literature review on the biological activity of S-carvone, geraniol and deri... more This work presents a literature review on the biological activity of S-carvone, geraniol and derivatives of these compounds, which are formed in the process of isomerization (during the process of geraniol isomerization, oxidation products of this compound are also obtained). Moreover, this work presents preliminary microbiological tests of creams with the addition of these biologically active compounds: S-carvone, geraniol, carvacrol (an S-carvone isomerization product), nerol (a geraniol isomerization product), linalool (a geraniol isomerization product) and citral (a geraniol oxidation product). Because the post-reaction mixture obtained after the S-carvone isomerization has a relatively simple composition, it was also added to creams and tested without isolating pure compounds. This may be a cheaper alternative to creams prepared with the addition of pure compounds. The mixture obtained after the geraniol isomerization process has a very complex composition; therefore, only comp...
The isomerization of limonene over the Ti-SBA-15 catalyst, which was prepared by the hydrothermal... more The isomerization of limonene over the Ti-SBA-15 catalyst, which was prepared by the hydrothermal method, was studied. The main products of limonene isomerization were terpinolene, α-terpinene, γ-terpinene, and p-cymene—products with numerous applications. The amount of these products depended on reaction time, temperature, and catalyst content. These parameters changed in the following range: reaction time 30–1380 min, temperature 140–160 °C, and catalyst content 5–15 wt %. Finally, the most favorable conditions for the limonene isomerization process were established: a reaction time of 180 min, temperature of 160 °C, and amount of the catalyst 15 wt %. In order to obtain p-cymene (dehydroaromatization product), the most favorable conditions are similar but the reaction time should be 1380 min. The application of such conditions allowed us to obtain the highest amounts of the desired products in the shortest time.
The antimicrobial properties of natural limonene and the compounds obtained after isomerization o... more The antimicrobial properties of natural limonene and the compounds obtained after isomerization of limonene (α-terpinene, γ-terpinene, terpinolene, and p-cymene) were studied. The following microorganisms were selected for the tests: Gram-negative bacteria Escherichia coli K12 (ACCT 25922), Gram-positive Staphylococcus epidermidis (ACCT 49461), yeast fungi Candida albicans, and fungi Trichophyton rubrum, Aspergillus niger, Penicillium commune, Trichoderma viride, and Cladosporium cladosporioides. During the studies, terpinolene showed the highest activity, and therefore, this compound was chosen for the preparation of therapeutic creams (content of terpinolene: 0.5 and 2 wt%). The obtained creams were active in the microbiological tests even at the lowest content of terpinolene. The mixture of products obtained after the isomerization of limonene also showed antimicrobial activity. Probably, in the future, this mixture of products can be used as a potential and relatively inexpensiv...
This work presents studies on the activity of the Ti-SBA-16 (SBA—Santa Barbara Amorphous) catalys... more This work presents studies on the activity of the Ti-SBA-16 (SBA—Santa Barbara Amorphous) catalyst in the isomerization of limonene and S-carvone. The Ti-SBA-16 catalyst was synthesized by a two-step method: first, the SBA-16 material was produced, and then it was impregnated with the titanium source. The Ti-SBA-16 catalyst was subjected to detailed characterizations by means of instrumental methods: XRD (X-ray Diffraction), UV-Vis (Ultraviolet–Visible) spectroscopy, FTIR (Fourier-Transform Infrared) spectroscopy, SEM (Scanning Electron Microscopy) with EDX (Energy Dispersive X-ray) spectroscopy, and EDXRF (Energy Dispersive X-ray Fluorescence). Both limonene and S-carvone underwent isomerization over the Ti-SBA-16 catalyst. In the isomerization of limonene, the main product was terpinolene, and its highest yield amounted to 39 mol% after 300 min at 170 °C with a catalyst content of 15 wt%. Under these conditions, the conversion of limonene reached 78 mol%. In contrast, the highest ...
: The interest in biologically active compounds of natural origin has increased significantly rec... more : The interest in biologically active compounds of natural origin has increased significantly recently. Studies of scientists focuses on the activity of these compounds, as well as their modifications, which allow wide range of use in pharmacology. With the present knowledge and technologies, it is possible to obtain compounds with increased biological activity and targeted acting. Curcuminoids are the main components of turmeric (Curcuma longa L.), a plant from India and South-East Asia. Due to its intense yellow-orange color and pleasant aroma, the powdered rootstalk is widely used in food industry, as natural dye and spice. The chemical compound responsible for the characteristic color of rhizomes of curcuma is 1,6-heptadien-3,5-dione-1,7-bis(4-hydroxy-3-methoxyphenyl) - (1E, 6E) called curcumin. This work aims to characterize curcumin in terms of its structure, therapeutic properties and also as a substrate for the synthesis of valuable derivatives. Knowledge about this relationship based on literature analysis will enable a better understanding of the factors responsible for its biological activity.
ABSTRAKTWstęp: Limonen jest monoterpenem, który w przyrodzie występuje w formie dwóch izomerów R ... more ABSTRAKTWstęp: Limonen jest monoterpenem, który w przyrodzie występuje w formie dwóch izomerów R i S. Z tych dwóch izomerów szczególną uwagę zwraca się obecnie na R-(+)-limonen, głównie ze względu na łatwość jego pozyskania z tanich i odnawialnych surowców naturalnych (odpadowe skórki pomarańczy) oraz bardzo liczne i różnorodne zastosowania, m.in. w medycynie, kosmetyce i przemyśle perfumeryjnym.Materiały i metody: Artykuł jest pracą przeglądową, w której omówiono zastosowania limonenu, przy czym duży nacisk został położony na opisanie zastosowań tego związku w medycynie. Z danych literaturowych wynika, że limonen w wielu przypadkach wykazuje działanie lecznicze. W artykule zwrócono także uwagę na bezpieczeństwo stosowania limonenu, czego dowodem są opisywane w literaturze wyniki doświadczeń przeprowadzonych na ludziach i zwierzętach. Opisano również metabolizm limonenu w organizmie człowieka, a także badania nad alergizującym wpływem produktów utlenienia limonenu, zarówno izomeru S...
This work describes research on the isomerization of R(+)-limonene over the Ti-MCM-41 catalyst. T... more This work describes research on the isomerization of R(+)-limonene over the Ti-MCM-41 catalyst. The studies showed that the Ti-MCM-41 catalyst is an active catalyst in the isomerization of R(+)-limonene. As a result of the isomerization of this compound, it is possible to obtain α-terpinene, γ-terpinene, terpinolene and p-cymene. Terpinolene is the main product of this process, and p-cymene is formed by the alpha-terpinene, gamma-terpinene and terpinolene dehydrogenation. The aforementioned products are of great practical importance. The most favorable reaction conditions leading to the obtaining of limonene isomerization products is the use of the catalyst in an amount of 15 wt% and the temperature of 160 °C. Depending on whether the desired products are the isomers of limonene (γ-terpinene, α-terpinene and terpinolene) or the product of their dehydroaromatization (β-cymene), it is possible to shorten or extend the reaction time. The method for the isomerization of limonene on the ...
The isomerization of limonene over natural the zeolite, clinoptilolite, was studied. The main pro... more The isomerization of limonene over natural the zeolite, clinoptilolite, was studied. The main products of limonene isomerization were terpinolene, α-terpinene, γ-terpinene and p-cymene. These products have numerous applications in the cosmetic, food and pharmaceutical industries. The main parameters affecting limonene isomerization were reaction time, temperature and catalyst content. These parameters varied within the following ranges: reaction time 15–1440 min; temperature 155–175°C; and catalyst content 5–15 wt.%. Terpinolene was obtained after reaction for 60 min at 175°C using 10 wt.% catalyst. p-Cymene was produced using similar conditions as for terpinolene except for a longer reaction time of 1440 min. The use of optimum experimental conditions allowed the greatest amounts of the desired products to be obtained in the shortest time.
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