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EP0035683A1 - Process for the production of aromatic substances - Google Patents

Process for the production of aromatic substances Download PDF

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Publication number
EP0035683A1
EP0035683A1 EP81101285A EP81101285A EP0035683A1 EP 0035683 A1 EP0035683 A1 EP 0035683A1 EP 81101285 A EP81101285 A EP 81101285A EP 81101285 A EP81101285 A EP 81101285A EP 0035683 A1 EP0035683 A1 EP 0035683A1
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EP
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Prior art keywords
tobacco
extract
radiation
irradiated
carotenoids
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EP81101285A
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German (de)
French (fr)
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EP0035683B1 (en
Inventor
Ursula Brümmer
Volker Heeman
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British American Tobacco Germany GmbH
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BAT Cigarettenfabriken GmbH
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Publication of EP0035683A1 publication Critical patent/EP0035683A1/en
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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 which can be used as flavoring tobacco additives.
  • fresh tobacco plants contain various natural substances that affect abakaroma as Raucharomaprecursoren T.
  • the surface resin of fresh tobacco plants which can be obtained by briefly “washing” the plants, contains the diterpenes, in particular Duvane, which are valuable as precursors.
  • the separation of these diterpenes is known from DE-OS 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 also known.
  • an known alcoholic extract containing carotenoids is produced from green tobacco plants or parts thereof, from which chlorophyll and, if appropriate, the waxy ones present on the surface of the tobacco plants Diterpene components are removed, and this extract and / or other xanthophyll-containing plant extracts are oxidized in alcoholic solution under UV radiation with oxygen.
  • green tobacco plants whose surface resin, e.g. by washing with methylene chloride.
  • plants which still contain the surface resin because under certain circumstances 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.
  • Extracts of other plants rich in xanthophyll can also be used, e.g. 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 possible, e.g. 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 fluctuate 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 irradiation takes place in the presence of sensitizers.
  • Diterpene fractions isolated from the surface resin are used to clarify the surface mix structure has already been irradiated in the presence of oxygen and sensitizers, ie 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.
  • products have the flavors obtained in the invention with numerous carboxyl and carbonyl groups with an otherwise unknown constitution to, among other ydroxycarbonsäüren keto carboxylic acids, and (usually lactonized.) H.
  • 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 may be jeinank as N. tomentosiformis, glutinosa or sylvestris or known tobacco and tobacco plants hybrids ren from conventional Tabakültu- '.
  • 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 ready-made tobacco e.g. be given up 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. on silica gel.
  • the irradiated extract is concentrated; the concentrated solution is applied to a silica gel column.
  • various solvents with increasing polarity As a first eluent e.g. Hexane can be used; the eluate contains hydrocarbons that can be discarded.
  • 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.
  • polar solvents e.g. Methanol, to which ⁇ 1% o acetic acid is added, valuable carboxylic acids, especially keto carboxylic acids, are isolated. Polymer and possibly highly polar compounds remain in the column.
  • Distillation is another suitable fractionation process. Even distilling off methanol from the irradiated extract at room temperature leads to vacuum 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.
  • Usual UV lamps are suitable for the irradiation, e.g. High-pressure mercury lamps or the like.
  • 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 saturated with sodium chloride solution mixed 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 / 1 of methanol being established.
  • 300 ml of an extract obtained above are placed in a 500 ml reactor and irradiated for 10 hours at room temperature with stirring using a high-pressure mercury lamp (Philips high-pressure burner HPK 125), a constant stream of synthesis air being 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 column is first eluted with hexane; the eluate, which mainly contains hydrocarbons, is discarded.
  • the mixture is then eluted with ether; this fraction contains i.a. 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 ⁇ 1% o acetic acid has been added.
  • the collected eluates are evaporated in vacuo at room temperature, taken up in ethanol and then sprayed onto ready-made tobacco.
  • the reaction mixture freed from methanol becomes one Subject to steam distillation, the distillate saturated with NaCl and shaken with diethyl ether.
  • the extract, which has been freed from ether, is applied to ready-made tobacco.
  • a commercially available xanthophyll paste is dissolved in methanol (xanthophyll concentration 1-50 g / 1). 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)

Abstract

Aromastoffe für Tabak mit verbesserten Aromaeigenschaften werden erhalten, indem man einen aus frischen Tabakpflanzen gewonnenen, Carotenoide enthaltenden alkoholischen Extrakt, aus dem die Diterpenkomponenten entfernt wurden, und/oder andere Xanthophyll-haltige Pflanzenextrakte herstellt und diese Extrakte in alkoholischer Lösung unter UV-Bestrahlung mit Sauerstoff oxidiert.Flavorings for tobacco with improved aroma properties are obtained by producing an alcoholic extract, obtained from fresh tobacco plants, containing carotenoids, from which the diterpene components have been removed, and / or other xanthophyll-containing plant extracts, and these extracts in alcoholic solution under UV radiation with oxygen oxidized.

Description

Die Erfindung betrifft ein Verfahren zur Herstellung von Aromastoffen, die als aromatisierende Tabakadditive eingesetzt werden können.The invention relates to a process for the production of flavorings which 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-OS 29 18 920 bekannt. Die danach erhaltenen Diterpen-Fräktionen können nach Isolierung und Reinigung fertigkonfektioniertem Tabak zugesetzt werden.It is known that fresh tobacco plants contain various natural substances that affect abakaroma as Raucharomaprecursoren T. The surface resin of fresh tobacco plants, which can be obtained by briefly “washing” the plants, contains the diterpenes, in particular Duvane, which are valuable as precursors. The separation of these diterpenes is known from DE-OS 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 Carotenoide auf, die ebenfalls Aromaprecursoren darstellen. Die Isolierung dieser Carotenoide in Form alkoholischer Extrakte ist ebenfalls 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 also known.

Es wurde nun gefunden, daß man diese Carotenoide 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 man aus grünen Tabakpflanzen oder Teilen derselben einen an sich bekannten alkoholischen, Carotenoide enthaltenden Extrakt herstellt, aus dem Chlorophyll sowie ggf. die auf der Oberfläche der Tabakpflanzen vorhandenen wachsartigen Diterpen-Komponenten entfernt sind, und diesen Extrakt und/oder andere Xanthophyllhaltige Pflanzenextrakte in alkoholischer Lösung unter UV-Bestrahlung mit Sauerstoff oxidiert.This object is achieved in that an known alcoholic extract containing carotenoids is produced from green tobacco plants or parts thereof, from which chlorophyll and, if appropriate, the waxy ones present on the surface of the tobacco plants Diterpene components are removed, and this extract and / or other xanthophyll-containing plant extracts are oxidized in alcoholic solution under UV radiation with oxygen.

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.In particular, green tobacco plants whose surface resin, e.g. by washing with methylene chloride. However, it is also possible to use plants which still contain the surface resin, because under certain circumstances 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. Extracts of other plants rich in xanthophyll can also be used, e.g. commercially available xanthophyll, which is usually commercially available in paste form.

Gemäß dem Verfahren der Erfindung nimmt man die Bestrahlung vorzugsweise bei einer Wellenlänge von 220-580`nm vor.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 possible, e.g. 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 Carotenoide, 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 fluctuate 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 Carotenoiden Aromaprecursoren bzw. Aromastoffe mit besonders vorteilhaften Eigenschaften erhalten lassen.According to a further advantageous embodiment of the method of the invention, the irradiation takes place in the presence of sensitizers. Diterpene fractions isolated from the surface resin are used to clarify the surface mix structure has already been irradiated in the presence of oxygen and sensitizers, ie 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 Radikalmechanismus. Demgemäß weisen die erfindungsgemäß erhaltenen Aromastoffe Produkte mit zahlreichen Carboxyl- und Carbonylgruppen bei im übrigen unbekannter Konstitution auf, unter anderem Ketocarbonsäuren sowie (meist lactonisierte.) Hydroxycarbonsäüren. 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 products have the flavors obtained in the invention with numerous carboxyl and carbonyl groups with an otherwise unknown constitution to, among other ydroxycarbonsäüren keto carboxylic acids, and (usually lactonized.) H. 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 Carotenoide können insbesondere Nicotinia-Arten wie N. tomentosiformis, glutinosa oder sylvestris oder bekannte Tabak-Hybride sowie Tabakpflanzen aus üblichen Tabakültu- ren'jeingesetzt werden. Dabei können insbesondere auch solche Tabakarten verwendet werden, die an sich als Rauchtabak ungeeignet sind.As a starting material for the production of the above carotenoids in particular Nicotinia species may be jeingesetzt as N. tomentosiformis, glutinosa or sylvestris or known tobacco and tobacco plants hybrids ren from conventional Tabakültu- '. 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 Ethanol, 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 ready-made tobacco e.g. be given up 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 Kieselgel-Säule 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'.Ether eluiert; diese Fraktion enthält überwiegend wertvolle Lactone, erhalten aus bei der Photooxidation der Carotenoide gebildeten Hydroxycarbonsäuren, sowie Ketone und Aldehyde. Schließlich können noch mit polaren Lösungsmitteln, z.B. Methanol, dem ≤ 1%o Essigsäure zugesetzt ist, wertvolle Carbonsäüren, insbesondere Ketocarbonsäuren, isoliert werden. In der Säule zurück bleiben Polymere sowie ggf. hochpolare Verbindungen.A first possibility of fractionation is column chromatography, e.g. 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 a first eluent e.g. 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, polar solvents, e.g. Methanol, to which ≤ 1% o acetic acid is added, valuable carboxylic acids, especially keto carboxylic 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. Even distilling off methanol from the irradiated extract at room temperature leads to vacuum 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. Usual UV lamps are suitable for the irradiation, e.g. 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 Carotenoid-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 l/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 tobacco parts 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 Petrolether/Ether (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/1 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 saturated with sodium chloride solution mixed 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 / 1 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 for 10 hours at room temperature with stirring using a high-pressure mercury lamp (Philips high-pressure burner HPK 125), a constant stream of synthesis air being 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 Ether 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 ≤ 1%o 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. The mixture is then eluted with ether; this fraction contains i.a. 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 ≤ 1% o acetic acid has been added.

Die gesammelten Eluate werden bei Raumtemperatur im Vakuum eingedampft, in Ethanol 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.The procedure is as in Example 1, but about 10 mg of bengal pink are added in the photooxidation stage.

Der von Methanol befreite Reaktionsansatz wird einer Wasserdampfdestillation unterworfen, das Destillat mit NaCl gesättigt und mit Diethylether ausgeschüttelt. Der von Ether befreite Extrakt wird auf fertigkonfektionierten Tabak aufgebracht.The reaction mixture freed from methanol becomes one Subject to steam distillation, the distillate saturated with NaCl and shaken with diethyl ether. The extract, which has been freed from ether, is applied to ready-made tobacco.

Beispiel 3Example 3

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

Claims (8)

1. Verfahren zur Herstellung von Aromastoffen, dadurch gekennzeichnet, daß man aus grünen Tabakpflanzen oder Teilen derselben einen an sich bekannten alkoholischen Carotenoide enthaltenden Extrakt herstellt, aus dem Chlorophyll sowie ggf. die auf der Oberfläche der Tabakpflanzen vorhandenen wachsartigen Diterpen-Komponenten entfernt sind, und diesen Extrakt und/oder andere Xanthophyll-haltige Pflanzenextrakte in alkoholischer Lösung unter UV-Bestrahlung mit Sauerstoff oxidiert.1. A process for the production of flavorings, characterized in that an extract containing known alcoholic carotenoids is prepared from green tobacco plants or parts thereof, from which chlorophyll and, if appropriate, the wax-like diterpene components present on the surface of the tobacco plants are removed, and oxidize this extract and / or other xanthophyll-containing plant extracts in alcoholic solution under UV radiation with oxygen. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Bestrahlung bei einer Wellenlänge von 220-580 nm vornimmt.2. The method according to claim 1, characterized in that one carries out the irradiation at a wavelength of 220-580 nm. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß man die Bestrahlung bei Raumtemperatur vornimmt.3. The method according to claim 1 or 2, characterized in that one carries out the irradiation at room temperature. 4. Verfahren nach einem der Ansprüche 1-3, dadurch gekennzeichnet, daß man den Extrakt eine Stunde bis 10 Tage, insbesondere 10-24 Stunden, bestrahlt.4. The method according to any one of claims 1-3, characterized in that the extract is irradiated for one hour to 10 days, in particular 10-24 hours. 5. Verfahren nach einem der Ansprüche 1-4, dadurch gekennzeichnet, daß die Bestrahlung in Gegenwart von Sensibilisatoren erfolgt.5. The method according to any one of claims 1-4, characterized in that the radiation is carried out in the presence of sensitizers. 6. Verfahren nach einem der Ansprüche 1-4, dadurch gekennzeichnet, daß die Bestrahlung in Abwesenheit von Sensibilatoren erfolgt.6. The method according to any one of claims 1-4, characterized in that the radiation is carried out in the absence of sensitizers. 7. Verfahren nach einem der Ansprüche 1-6, dadurch ge- kennzeichnet, daß man den bestrahlten Extrakt auf fertigkonfektionierten Tabak aufgibt.7. The method according to any one of claims 1-6, characterized g e - indicates that the irradiated extract is placed on ready-made tobacco. 8. Verfahren nach einem der Ansprüche 1-7, dadurch gekennzeichnet, daß man den bestrahlten Extrakt vor der Aufgabe auf den Tabak fraktioniert.8. The method according to any one of claims 1-7, characterized in that the irradiated extract is fractionated on the tobacco before the task.
EP81101285A 1980-03-08 1981-02-23 Process for the production of aromatic substances Expired EP0035683B1 (en)

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DE3009031C2 (en) 1983-04-21
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US4351346A (en) 1982-09-28
AU537210B2 (en) 1984-06-14
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ZA81868B (en) 1982-03-31
EP0035683B1 (en) 1983-11-16

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