EP0035683B1 - Process for the production of aromatic substances - Google Patents

Process for the production of aromatic substances Download PDF

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Publication number
EP0035683B1
EP0035683B1 EP81101285A EP81101285A EP0035683B1 EP 0035683 B1 EP0035683 B1 EP 0035683B1 EP 81101285 A EP81101285 A EP 81101285A EP 81101285 A EP81101285 A EP 81101285A EP 0035683 B1 EP0035683 B1 EP 0035683B1
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Prior art keywords
tobacco
process according
extract
irradiation
carried out
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EP81101285A
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German (de)
French (fr)
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EP0035683A1 (en
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Ursula Brümmer
Volker Heeman
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British American Tobacco Germany GmbH
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BAT Cigarettenfabriken GmbH
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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction

Definitions

  • the invention relates to a process for the production of flavorings using an alcoholic extract obtained from green tobacco plants or parts thereof, containing carotenoids, from which chlorophyll and, if appropriate, the wax-like diterpene components present on the surface of the tobacco plants are removed, and / or by others Plant extracts containing xanthophyll in alcoholic solution.
  • the flavorings produced according to the invention can be used as flavoring tobacco additives.
  • fresh tobacco plants contain various natural substances which, as smoke aroma precursors, influence the tobacco aroma.
  • the surface resin of fresh tobacco plants which can be obtained by briefly washing the plants, contains the valuable diterpenes, especially Duvane, as precursors.
  • the separation of these diterpenes is known from DE-A-29 18 920. The diterpene fractions obtained after this can be added to ready-made tobacco after isolation and purification.
  • Carotenoids which are also aroma precursors, still occur in the tobacco plants themselves.
  • the isolation of these carotenoids in the form of alcoholic extracts is known from Tobacco Science 2, 81 (1958).
  • the surface resin for. B. was removed by washing with methylene chloride.
  • plants can also be used which still contain the surface resin, because u. U.
  • the diterpenes obtained in the surface resin can also be converted into valuable aroma precursors or aroma substances during the treatment according to the invention.
  • Xanthophyll-rich extracts from other plants can also be used, e.g. B. commercially available xanthophyll, which is usually commercially available in paste form.
  • the irradiation is preferably carried out at a wavelength of 220-580 nm.
  • the radiation is usually at room temperature; however, other temperatures are also possible, e.g. B. Temperatures between - 20 ° C and the boiling point of the solvent used.
  • the duration of the radiation depends on the size of the radiation approach, the respective type of carotenoids, which can vary depending on the tobacco plants, and the power of the UV source.
  • the radiation duration is generally from one hour to 10 days, in particular 6-24 hours.
  • the radiation is carried out in the presence of sensitizers.
  • Diterpene fractions isolated from the surface resin for clarifying the chemical structure are already present in the presence of oxygen and sensitizers, i.e. H. irradiated with singlet oxygen, cf. Acta Chemica Scandinavica 1979, pp. 437-442;
  • sensitizers i.e. H. irradiated with singlet oxygen, cf. Acta Chemica Scandinavica 1979, pp. 437-442;
  • aroma precursors or aroma substances are obtained if the radiation is carried out in the absence of the aforementioned sensitizers.
  • the photooxidation then no longer takes place through singlet oxygen, but rather according to a conventional radical mechanism.
  • the flavorings obtained according to the invention have products with numerous carboxyl and carbonyl groups with an otherwise unknown constitution, including ketocarboxylic acids and (mostly lactonized) hydroxycarboxylic acids.
  • the improvement in the properties of the aroma precursors or aroma substances achieved according to this process variant is surprising, since under these process conditions a considerably greater destruction of the aroma substances had to be expected.
  • Nicotinia species such as N. tomentosiformis, glutinosa or sylvestris or known tobacco hybrids and tobacco plants from conventional tobacco cultures can be used as the starting material for the production of the above-mentioned carotenoids.
  • those types of tobacco that are unsuitable as smoking tobacco can be used.
  • Lower alcohols in particular methanol and ethanol, can be used as solvents for the diterpene fraction to be irradiated.
  • the irradiated extracts can, if necessary after prior concentration, directly on finished tobacco z. B. be applied by spraying.
  • the irradiated extracts are fractionated onto the tobacco before they are introduced.
  • the purpose of this fractionation is to separate undesired products with a low boiling point and polymeric products which have a negative effect on the tobacco aroma or can do nothing to improve it.
  • Different methods can be used for the fractionation.
  • a first possibility of fractionation is column chromatography, e.g. B. on silica gel.
  • the irradiated extract is concentrated; the concentrated solution is applied to a silica gel column.
  • various solvents with increasing polarity.
  • the first eluent e.g. B. hexane can be used; the eluate contains hydrocarbons that can be discarded.
  • ether this fraction mainly contains valuable lactones, obtained from hydroxycarboxylic acids formed in the photooxidation of the carotenoids, and also ketones and aldehydes.
  • polar solvents e.g. As methanol, the ⁇ 10 s h acetic acid is added, valuable carboxylic acids, especially ketocarboxylic acids, are isolated. Polymer and possibly highly polar compounds remain in the column.
  • Distillation is another suitable fractionation process.
  • methanol from the irradiated extract at room temperature in a vacuum leads to the removal of unwanted, volatile components.
  • This can be followed by a high vacuum distillation, preferably collecting the fractions which pass at 0.02 Torr at temperatures of up to 100 ° C.
  • Another suitable fractionation method is steam distillation, in which the components that are volatile with water vapor are collected.
  • the process of the invention is preferably carried out by passing an air or oxygen stream through the extract and simultaneously irradiating it with a UV source which provides a wavelength of 220-580 nm.
  • a UV source which provides a wavelength of 220-580 nm.
  • Conventional UV lamps e.g. B. high-pressure mercury lamps or the like.
  • Preparation of an alcoholic carotenoid fraction Parts of fresh green tobacco plants, namely stems and leaves, are washed 2 ⁇ 30 seconds with methylene chloride in an amount of 1 l / kg parts of tobacco to remove the diterpene-rich surface resin.
  • the plant parts thus obtained are homogenized in methanol.
  • the homogenate is centrifuged, the centrifugate is mixed with KOH solution (KOH content 15%, based on the tobacco fresh weight); it is left overnight to destroy the chlorophyll at room temperature.
  • the solution is mixed with a saturated sodium chloride solution with petroleum ether / ether (1: 1).
  • the organic phase is evaporated in vacuo at room temperature.
  • the residue is taken up in methanol, a concentration of 1-50 g of solid / l of methanol being established.
  • 300 ml of an extract obtained above are placed in a 500 ml reactor and irradiated at room temperature with stirring with a high pressure mercury lamp (Philips high pressure burner HPK 125) for 10 hours, whereby a constant stream of synthesis air is bubbled through the solution.
  • a high pressure mercury lamp Philips high pressure burner HPK 125
  • the irradiated extract obtained above is concentrated and placed on a column filled with silica gel.
  • the collected eluates are evaporated in vacuo at room temperature, taken up in ethanol and then sprayed onto ready-made tobacco.
  • Example 2 The procedure is as in Example 1, but about 10 mg of bengal pink are added in the photooxidation stage.
  • the reaction mixture freed from methanol is subjected to steam distillation, the distillate is saturated with NaCl and extracted with diethyl ether.
  • the ether-free extract is applied to ready-made tobacco.
  • a commercially available xanthophyll paste is dissolved in methanol (xanthophyll concentration 1-50 g / l). Irradiation and workup are carried out as in Example 1.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Die Erfindung betrifft ein Verfahren zum Herstellen von Aromastoffen unter Verwendung eines aus grünen Tabakpflanzen oder Teilen derselben gewonnenen, Carotinoide enthaltenden alkoholischen Extrakts, aus dem Chlorophyll sowie ggf. die auf der Oberfläche der Tabakplanzen vorhandenen wachsartigen Diterpen-Komponenten entfernt sind, und/oder von anderen Xanthophyll-haltigen Pflanzenextrakten in alkoholischer Lösung. Die erfindungsgemäß hergestellten Aromastoffe können als aromatisierende Tabakadditive eingesetzt werden.The invention relates to a process for the production of flavorings using an alcoholic extract obtained from green tobacco plants or parts thereof, containing carotenoids, from which chlorophyll and, if appropriate, the wax-like diterpene components present on the surface of the tobacco plants are removed, and / or by others Plant extracts containing xanthophyll in alcoholic solution. The flavorings produced according to the invention can be used as flavoring tobacco additives.

Es ist bekannt, daß frische Tabakpflanzen verschiedene Naturstoffe enthalten, die als Raucharomaprecursoren das Tabakaroma beeinflussen. So enthält das Oberflächenharz frischer Tabakpflanzen, das durch kurzzeitiges «Waschen der Pflanzen gewonnen werden kann, die als Precursoren wertvollen Diterpene, insbesondere Duvane. Die Abtrennung dieser Diterpene ist aus der DE-A-29 18 920 bekannt. Die danach erhaltenen Diterpen-Fraktionen können nach Isolierung und Reinigung fertigkonfektioniertem Tabak zugesetzt werden.It is known that fresh tobacco plants contain various natural substances which, as smoke aroma precursors, influence the tobacco aroma. The surface resin of fresh tobacco plants, which can be obtained by briefly washing the plants, contains the valuable diterpenes, especially Duvane, as precursors. The separation of these diterpenes is known from DE-A-29 18 920. The diterpene fractions obtained after this can be added to ready-made tobacco after isolation and purification.

Es treten in den Tabakpflanzen selbst noch Carotinoide auf, die ebenfalls Aromaprecursoren darstellen. Die Isolierung dieser Carotinoide in Form alkoholischer Extrakte ist aus Tobacco Science 2, 81 (1958) bekannt.Carotenoids, which are also aroma precursors, still occur in the tobacco plants themselves. The isolation of these carotenoids in the form of alcoholic extracts is known from Tobacco Science 2, 81 (1958).

Es wurde nun gefunden, daß man diese Carotinoide durch geeignete Maßnahmen modifizieren kann, so daß man Aromaprecursoren bzw. Aromastoffe erhalten kann, die den Rauchgeschmack des Tabaks besonders vorteilhaft beeinflussen.It has now been found that these carotenoids can be modified by suitable measures, so that aroma precursors or aroma substances can be obtained which have a particularly advantageous effect on the smoking taste of the tobacco.

Diese Aufgabe wird erfindungsgemäß dadurch gelöst, daß diese Extrakte unter UV-Bestrahlung mit Sauerstoff oxidiert werden.This object is achieved in that these extracts are oxidized with UV radiation with oxygen.

Zwar ist aus der GB-A-1 316172 bekannt, Rauchtabak Carotinoide zur Geschmacksverbesserung zuzusetzen, eine Oxidation dieser Carotinoide mit Sauerstoff unter UV-Bestrahlung ist in dieser Veröffentlichung jedoch nicht beschrieben.Although it is known from GB-A-1 316172 to add smoking tobacco carotenoids to improve taste, oxidation of these carotenoids with oxygen under UV radiation is not described in this publication.

Als Ausgangsmaterial für das Verfahren der Erfindung kommen insbesondere grüne Tabakpflanzen in Frage, deren Oberflächenharz, z. B. durch Waschung mit Methylenchlorid, entfernt wurde. Es können jedoch auch Pflanzen verwendet werden, die das Oberflächenharz noch enthalten, denn u. U. können auch die im Oberflächenharz erhaltenen Diterpene während der erfindungsgemäßen Behandlung in wertvolle Aromaprecursoren bzw. Aromastoffe umgewandelt werden. Weiterhin können auch Xanthophyll-reiche Extrakte anderer Pflanzen eingesetzt werden, z. B. handelsübliches Xanthophyll, das meist in Pastenform im Handel erhältlich ist. Gemäß dem Verfahren der Erfindung nimmt man die Bestrahlung vorzugsweise bei einer Wellenlänge von 220-580 nm vor.As a starting material for the method of the invention, in particular green tobacco plants come into question, the surface resin, for. B. was removed by washing with methylene chloride. However, plants can also be used which still contain the surface resin, because u. U. The diterpenes obtained in the surface resin can also be converted into valuable aroma precursors or aroma substances during the treatment according to the invention. Xanthophyll-rich extracts from other plants can also be used, e.g. B. commercially available xanthophyll, which is usually commercially available in paste form. According to the method of the invention, the irradiation is preferably carried out at a wavelength of 220-580 nm.

Die Bestrahlung erfolgt gewöhnlich bei Raumtemperatur ; es sind jedoch auch andere Temperaturen möglich, z. B. Temperaturen zwischen - 20 °C und dem Siedepunkt des verwendeten Lösungsmittels.The radiation is usually at room temperature; however, other temperatures are also possible, e.g. B. Temperatures between - 20 ° C and the boiling point of the solvent used.

Die Dauer der Bestrahlung richtet sich nach der Größe des Bestrahlungsansatzes, der jeweiligen Art der Carotinoide, die in Abhängigkeit von den Tabakpflanzen schwanken kann, und der Leistung der UV-Quelle. Die Bestrahlungsdauer beträgt im allgemeinen eine Stunde bis 10 Tage, insbesondere 6-24 Stunden.The duration of the radiation depends on the size of the radiation approach, the respective type of carotenoids, which can vary depending on the tobacco plants, and the power of the UV source. The radiation duration is generally from one hour to 10 days, in particular 6-24 hours.

Gemäß einer weiteren vorteilhaften Ausführungsform des Verfahrens der Erfindung erfolgt die Bestrahlung in Gegenwart von Sensibilisatoren. Zwar sind aus dem Oberflächenharz isolierte Diterpenfraktionen zur Aufklärung der chemischen Struktur bereits in Gegenwart von Sauerstoff und Sensibilisatoren, d. h. mit Singulett-Sauerstoff, bestrahlt worden, vgl. Acta Chemica Scandinavica 1979, S. 437-442; es konnte jedoch nicht erwartet werden, daß sich bei einer entsprechenden Behandlung von Carotinoiden Aromaprecursoren bzw. Aromastoffe mit besonders vorteilhaften Eigenschaften erhalten lassen.According to a further advantageous embodiment of the method of the invention, the radiation is carried out in the presence of sensitizers. Diterpene fractions isolated from the surface resin for clarifying the chemical structure are already present in the presence of oxygen and sensitizers, i.e. H. irradiated with singlet oxygen, cf. Acta Chemica Scandinavica 1979, pp. 437-442; However, it could not be expected that aroma precursors or aroma substances with particularly advantageous properties could be obtained with a corresponding treatment of carotenoids.

Für die Durchführung des Verfahrens sind alle in der Photochemie üblichen geeigneten Sensibilisatoren verwendbar, insbesondere Bengalrosa.All suitable sensitizers customary in photochemistry can be used for carrying out the method, in particular rose bengal.

Besonders vorteilhafte Aromaprecursoren bzw. Aromastoffe werden jedoch erhalten, wenn man die Bestrahlung in Abwesenheit der vorgenannten Sensibilisatoren vornimmt. Die Photooxidation erfolgt dann nicht mehr durch Singulett-Sauerstoff, sondern vielmehr nach einem üblichen Radikal-mechanismus. Demgemäß weisen die erfindungsgemäß erhaltenen Aromastoffe Produkte mit zahlreichen Carboxyl- und Carbonylgruppen bei im übrigen unbekannter Konstitution auf, unter anderem Ketocarbonsäuren sowie (meist lactonisierte) Hydroxycarbonsäuren. Die gemäß dieser Verfahrensvariante erreichte Verbesserung der Eigenschaften der Aromaprecursoren bzw. Aromastoffe ist überraschend, da man unter diesen Verfahrensbedingungen eine erheblich stärkere Zerstörung der Aromastoffe erwarten mußte.However, particularly advantageous aroma precursors or aroma substances are obtained if the radiation is carried out in the absence of the aforementioned sensitizers. The photooxidation then no longer takes place through singlet oxygen, but rather according to a conventional radical mechanism. Accordingly, the flavorings obtained according to the invention have products with numerous carboxyl and carbonyl groups with an otherwise unknown constitution, including ketocarboxylic acids and (mostly lactonized) hydroxycarboxylic acids. The improvement in the properties of the aroma precursors or aroma substances achieved according to this process variant is surprising, since under these process conditions a considerably greater destruction of the aroma substances had to be expected.

Als Ausgangsmaterial für die Gewinnung der oben genannten Carotinoide können insbesondere Nicotinia-Arten wie N. tomentosiformis, glutinosa oder sylvestris oder bekannte Tabak-Hybride sowie Tabakpflanzen aus üblichen Tabakulturen eingesetzt werden. Dabei können insbesondere auch solche Tabakarten verwendet werden, die an sich als Rauchtabak ungeeignet sind.In particular, Nicotinia species such as N. tomentosiformis, glutinosa or sylvestris or known tobacco hybrids and tobacco plants from conventional tobacco cultures can be used as the starting material for the production of the above-mentioned carotenoids. In particular, those types of tobacco that are unsuitable as smoking tobacco can be used.

Als Lösungsmittel für die zu bestrahlende Diterpenfraktion können niedere Alkohole, insbesondere Methanol und Äthanol, eingesetzt werden. Die bestrahlten Extrakte können, ggf. nach vorheriger Konzentrierung, direkt auf fertigkonfektionierten Tabak z. B. durch Sprühen aufgegeben werden.Lower alcohols, in particular methanol and ethanol, can be used as solvents for the diterpene fraction to be irradiated. The irradiated extracts can, if necessary after prior concentration, directly on finished tobacco z. B. be applied by spraying.

Es hat sich jedoch als besonders vorteilhaft erwiesen, wenn man die bestrahlten Extrakte vor der Aufgabe auf den Tabak fraktioniert. Zweck dieser Fraktionierung ist die Abtrennung unerwünschter Produkte mit einem niedrigen Siedepunkt sowie polymerer Produkte, die das Tabakaroma nachteilig beeinflussen oder nichts zu seiner Verbesserung beitragen können. Für die Fraktionierung können verschiedene Verfahren herangezogen werden.However, it has proven to be particularly advantageous if the irradiated extracts are fractionated onto the tobacco before they are introduced. The purpose of this fractionation is to separate undesired products with a low boiling point and polymeric products which have a negative effect on the tobacco aroma or can do nothing to improve it. Different methods can be used for the fractionation.

Eine erste Möglichkeit der Fraktionierung ist die Säulenchromatographie, z. B. an Kieselgel. Dabei wird der bestrahlte Extrakt konzentriert; die eingeengte Lösung wird auf eine KieselgelSäule aufgegeben. Anschließend wird mit verschiedenen Lösungsmitteln mit ansteigender Polarität eluiert. Als erstes Eluierungsmittel kann z. B. Hexan eingesetzt werden ; das Eluat enthält Kohlenwasserstoffe, die verworfen werden können. Anschließend wird mit Äther eluiert ; diese Fraktion enthält überwiegend wertvolle Lactone, erhalten aus bei der Photooxidation der Carotinoide gebildeten Hydroxycarbonsäuren, sowie Ketone und Aldehyde. Schließlich können noch mit polaren Lösungsmitteln, z. B. Methanol, dem < 10 sh Essigsäure zugesetzt ist, wertvolle Carbonsäuren, insbesondere Ketocarbonsäuren, isoliert werden. In der Säule zurück bleiben Polymere sowie ggf. hochpolare Verbindungen.A first possibility of fractionation is column chromatography, e.g. B. on silica gel. The irradiated extract is concentrated; the concentrated solution is applied to a silica gel column. Then elute with various solvents with increasing polarity. As the first eluent, e.g. B. hexane can be used; the eluate contains hydrocarbons that can be discarded. Then elute with ether; this fraction mainly contains valuable lactones, obtained from hydroxycarboxylic acids formed in the photooxidation of the carotenoids, and also ketones and aldehydes. Finally, with polar solvents, e.g. As methanol, the <10 s h acetic acid is added, valuable carboxylic acids, especially ketocarboxylic acids, are isolated. Polymer and possibly highly polar compounds remain in the column.

Als weiteres Fraktionierungsverfahren eignet sich die Destillation. Bereits das Abdestillieren von Methanol aus dem bestrahlten Extrakt bei Raumtemperatur im Vakuum führt zu einer Entfernung unerwünschter, leicht flüchtiger Bestandteile. Daran kann sich eine Hochvakuumdestillation anschließen, wobei bevorzugt die Fraktionen gesammelt werden, die bei 0,02 Torr bei Temperaturen von bis zu 100 °C übergehen.Distillation is another suitable fractionation process. Already the distillation of methanol from the irradiated extract at room temperature in a vacuum leads to the removal of unwanted, volatile components. This can be followed by a high vacuum distillation, preferably collecting the fractions which pass at 0.02 Torr at temperatures of up to 100 ° C.

Eine weitere geeignete Fraktionierungsmethode ist die Wasserdampfdestillation, wobei die mit Wasserdampf flüchtigen Bestandteile gesammelt werden.Another suitable fractionation method is steam distillation, in which the components that are volatile with water vapor are collected.

Das Verfahren der Erfindung erfolgt vorzugsweise in der Weise, daß man einen Luft- bzw. Sauerstoffstrom durch den Extrakt leitet und diesen gleichzeitig mit einer UV-Quelle, die eine Wellenlänge von 220-580 nm liefert, bestrahlt. Für die Bestrahlung eignen sich übliche UV-Lampen, z. B. Hochdruck-Quecksilberlampen oder dergleichen.The process of the invention is preferably carried out by passing an air or oxygen stream through the extract and simultaneously irradiating it with a UV source which provides a wavelength of 220-580 nm. Conventional UV lamps, e.g. B. high-pressure mercury lamps or the like.

Das Verfahren der Erfindung wird im folgenden anhand von bevorzugten Ausführungsbeispielen näher erläutert.The method of the invention is explained in more detail below on the basis of preferred exemplary embodiments.

Beispiel 1example 1

Herstellung einer alkoholischen Carotinoid-Fraktion : Teile von frischen grünen Tabakpflanzen, nämlich Stengel und Blätter, werden zur Entfernung des Diterpen-reichen Oberflächenharzes 2 x 30 Sekunden lang mit Methylenchlorid in einer Menge von 1 I/kg Tabakteilen gewaschen.Preparation of an alcoholic carotenoid fraction: Parts of fresh green tobacco plants, namely stems and leaves, are washed 2 × 30 seconds with methylene chloride in an amount of 1 l / kg parts of tobacco to remove the diterpene-rich surface resin.

Die so erhaltenen Pflanzenteile werden in Methanol homogenisiert. Das Homogenisat wird zentrifugiert, das Zentrifugat wird mit KOH-Lösung (KOH-Gehalt 15 %, bezogen auf Tabakfrischgewicht) versetzt ; man läßt es über Nacht bei Raumtemperatur zur Zerstörung des Chlorophylls stehen. Anschließend wird die Lösung mit einer gesättigten Natriumchloridlösung versetzt mit Petroläther/Äther (1 : 1) ausgeschüttelt. Die organische Phase wird bei Raumtemperatur im Vakuum eingedampft. Der Rückstand wird in Methanol aufgenommen, wobei man eine Konzentration von 1-50 g Feststoff/I Methanol einstellt.The plant parts thus obtained are homogenized in methanol. The homogenate is centrifuged, the centrifugate is mixed with KOH solution (KOH content 15%, based on the tobacco fresh weight); it is left overnight to destroy the chlorophyll at room temperature. Then the solution is mixed with a saturated sodium chloride solution with petroleum ether / ether (1: 1). The organic phase is evaporated in vacuo at room temperature. The residue is taken up in methanol, a concentration of 1-50 g of solid / l of methanol being established.

PhotooxidationPhotooxidation

300 ml eines vorstehend erhaltenen Extrakts werden in einen 500 ml Reaktor gegeben und bei Raumtemperatur unter Rühren mit einer Quecksilber-Hochdrucklampe (Philips Hochdruckbrenner HPK 125) 10 Stunden lang bestrahlt, wobei man durch die Lösung einen ständigen Strom von Syntheseluft durchperlen läßt.300 ml of an extract obtained above are placed in a 500 ml reactor and irradiated at room temperature with stirring with a high pressure mercury lamp (Philips high pressure burner HPK 125) for 10 hours, whereby a constant stream of synthesis air is bubbled through the solution.

FraktionierungFractionation

Der vorstehend erhaltene bestrahlte Extrakt wird eingeengt und auf eine mit Kieselgel gefüllte Säule gegeben. Die Säule wird zunächst mit Hexan eluiert; das Eluat, das überwiegend Kohlenwasserstoffe enthält, wird verworfen. Anschließend wird mit Äther eluiert ; diese Fraktion enthält u. a. wertvolle Lactone, Ketone und Aldehyde und wird gesammelt. Ergibt die Analyse des Extrakts, daß dieser auch reich an freien Carbonsäuren und Ketocarbonsäuren ist, kann anschließend noch mit Methanol, dem s=10% Essigsäure zugesetzt ist, eluiert werden.The irradiated extract obtained above is concentrated and placed on a column filled with silica gel. The column is first eluted with hexane; the eluate, which mainly contains hydrocarbons, is discarded. Then elute with ether; this fraction contains valuable lactones, ketones and aldehydes and is collected. If the analysis of the extract shows that it is also rich in free carboxylic acids and ketocarboxylic acids, it can then be eluted with methanol, to which s = 10% acetic acid has been added.

Die gesammelten Eluate werden bei Raumtemperatur im Vakuum eingedampft, in Äthanol aufgenommen und anschließend auf fertigkonfektionierten Tabak gesprüht.The collected eluates are evaporated in vacuo at room temperature, taken up in ethanol and then sprayed onto ready-made tobacco.

Beispiel 2Example 2

Es wird wie in Beispiel 1 verfahren, wobei man jedoch in der Photooxidationsstufe ca. 10 mg Bengalrosa zusetzt. Der von Methanol befreite Reaktionsansatz wird einer Wasserdampfdestillation unterworfen, das Destillat mit NaCI gesättigt und mit Diäthyläther ausgeschüttelt. Der von Äther befreite Extrakt wird auf fertigkonfektionierten Tabak aufgebracht.The procedure is as in Example 1, but about 10 mg of bengal pink are added in the photooxidation stage. The reaction mixture freed from methanol is subjected to steam distillation, the distillate is saturated with NaCl and extracted with diethyl ether. The ether-free extract is applied to ready-made tobacco.

Beispiel 3Example 3

Eine handelsübliche Xanthophyll-Paste wird in Methanol gelöst (Xanthophyll-Konzentration 1-50 g/I). Bestrahlung und Aufarbeitung erfolgen wie in Beispiel 1.A commercially available xanthophyll paste is dissolved in methanol (xanthophyll concentration 1-50 g / l). Irradiation and workup are carried out as in Example 1.

Claims (8)

1. Process for the preparation of aroma substances using an alcoholic extract which has been prepared from green tobacco plants or parts thereof and from which chlorophyll and, optionally, the waxy diterpene components present on the surface of the tobacco plant have been removed, and/or other xanthophyll - containing plant extracts in alcoholic solutions, characterized in that these extracts are oxidized with oxygen under irradiation with UV light.
2. Process according to claim 1, characterized in that the irradiation is carried out at a wave length of 220-580 nm.
3. Process according to claim 1 or 2, characterized in that irradiation is carried out at room temperature.
4. Process according to one of claims 1-3, characterized in that the extract is irradiated for one hour to ten days and in particular for 10-24 hours.
J. process according to one of claims 1-4 characterized in that irradiation is carried out in the presence of sensitizers.
6. Process according to one of claims 1-4, characterized in that irradiation is carried out in the absence of sensitizers.
7. Process according to one of claims 1-6, characterized in that the irradiated extract is applied to conditioned tobacco.
8. Process according to one of claims 1-7, characterized in that the irradiated extract in fractionated before it is applied to the tobacco.
EP81101285A 1980-03-08 1981-02-23 Process for the production of aromatic substances Expired EP0035683B1 (en)

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DE3009031 1980-03-08
DE3009031A DE3009031C2 (en) 1980-03-08 1980-03-08 Process for the production of flavorings for smoking products

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EP0035683A1 EP0035683A1 (en) 1981-09-16
EP0035683B1 true EP0035683B1 (en) 1983-11-16

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EP81101285A Expired EP0035683B1 (en) 1980-03-08 1981-02-23 Process for the production of aromatic substances

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US4351346A (en) 1982-09-28
DE3009031A1 (en) 1981-09-17
EP0035683A1 (en) 1981-09-16
DE3009031C2 (en) 1983-04-21
BR8101303A (en) 1981-09-08
AU537210B2 (en) 1984-06-14
ZA81868B (en) 1982-03-31
CA1159641A (en) 1984-01-03
AU6805281A (en) 1981-09-17

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