DE3402893A1 - Tobacco aroma modifier and process for the preparation thereof - Google Patents

Abstract

A tobacco aroma modifier is obtained by bringing beta -ionone into contact with a fungal culture and converting at least some of the beta -ionone into a compound selected from group A, B or C. The compound A is preferably extracted from the product and then introduced into the smoking material. The invention also relates to the smoke modifier thus prepared. The level of loading with the smoke modifiers is in the range from 5 to 2,000 and preferably 100 to 500 parts/million of the smoking material.

Description

Tobacco Flavor Modifiers and Processes too

Manufacture thereof The invention relates to smoke flavor modifiers and a method for its production.

Smoke flavor modifiers are used in the tobacco mixer to add a to achieve the desired smoke aroma more reliably and / or more economically.

ß-ionone is a compound used in perfume manufacture. Its chemical name is 4- (2,6,6-trimethyl-1-cyclohexen-1 -yl) -3-buten-2-one.

It is available in stores. The β-ionone used according to the invention was sold by the Aldrich Chemical Company of Milwaukee, Wisconsin 53233, USA as one liquid obtained with a purity of 98% and a boiling point of 126 to 1280C.

According to the invention there is provided a method for producing a smoke flavor modifier shown, in which one brings ß-ionone into contact with a fungal culture and thereby at least part of the β-ionone in at least one compound from the group Compound A, Compound B and Compound C converts these compounds are each described in more detail below.

According to the present invention, there is a smoke flavor modifier, which can be introduced into a smoking material also consists of one or more Compounds from the group consisting of compound B and compound C.

A product of Compounds A, B and C can be used as a tobacco smoke flavor modifier be used. Alternatively, you can use one or more of the compounds that are preferred consist of or contain compound A, which is obtained in a higher yield, first and extract the extracted compound or compounds can then be used as a tobacco smoke flavor modifier.

The smoking material can be tobacco, reconstituted tobacco or a Be tobacco substitutes. The agent can be brought into the smoking material, by doing it is sprayed on dissolved in a liquid solvent. The means can be more appropriate Way to be added to the smoking material in an amount ranging from 5 to 2000 Parts / million of the smoking material, preferably in the range of 100 to 500 Parts / million.

The chemical structure of compound A, known as a compound per se, is the following: The chemical structure of compound B is the following: The chemical structure of compound C is the following: It was found that a large number of fungi in the conversion of ß-ionone with the formation of 2,6,6-trimethyl-1-cyclohexene-1-ethanol (compound A), 4-hydroxy-2,6,6- trimethyl-1-cyclohexene-1-ethanol (compound B) and 2-hydroxymethyl-6,6-dimethyl-1-cyclohexene-1-ethanol (compound C) can be used. Of 27 mushroom shake flask cultures, it was found that 11 of them effectively converted β-ionone to give compound A, although considerable differences in the degree of conversion were found. 5 of the 11 fungi also gave compounds B and C. These 11 fungi were identified as species of Aspergillus (3 strains), Penicillium (1 strain), Cladosporium (1 strain), Ophiobolus (1 strain), Abortiporus (1 strain), Beauveria (1 strain), yeast (1 strain) and Phoma (1 strain) identified. One could not be identified due to the lack of spore binding.

Examples of suitable fungi are: Cladosporium oxysporum CBS 548.80 Abortiporus ciennis CBS 365.74 Beauveria bassiana CBS 209.27 Ophiobolus herpotrichus CBS 240.31 All four of the above mushrooms are from Centraalbureau Voor Schimmelcultures, Oosterstraat 1, Baarn, Holland. The culture with the deposit number CBS 548.80 was deposited in the Centraalbureau Voor Schimmelcultures on May 25, 1980 and the properties are in British patent application 2 093 446, which is hereby incorporated into the disclosure, described.

The selection of microorganisms that have the property to convert ß-ionon with the formation of compounds A, B or C, was taken, by interfering with ß-ionone with a range of microorganisms from culture depositories obtained by direct isolation from natural substances such as soil or tobacco leaves, isolated, incubated. The new connections were identified by using the extracts obtained from the culture media Compared to controls of a culture medium which did not contain β-ionone.

The compounds were then isolated and purified and a predetermined one Part of it was incorporated into cigarette tobacco.

The cigarettes filled with this tobacco were then used by smoking experts smoked to determine the effect of the respective products on tobacco smoke. In all cases, the smokers exhibited a noticeable effect on the taste of the Smoke firmly without noticing any undesirable smoke attributes became.

The following examples describe the extraction process the ß-ionone compounds and the nature of the products obtained.

Example 1 A pure culture of Cladosporium oxysporum CBS 548.80 was made in two 250 ml Erlenmeyer flasks, each containing 100 ml of a sterile malt extract broth of the following composition contained, unoculated: Malt extract 17 g of mycological Peptone 3 g distilled water 1000 ml pH 5.4 The flasks were fitted with a planetary shaker at room temperature with a shaking speed of 150 rpm for 5 days incubated to allow C. oxysporum to grow. 100 mg ß-ionone, dissolved in polyoxyethylene sorbitol monooleate, obtained from Sigma Chemicals, Poole, England, under the trade name Tween 80, was then added to one of the two flasks and an equal amount was added to a third flask containing 100 ml of the sterile Malt extract but did not contain any fungus.

Incubation of the three flasks was continued for another 7 days and then the contents of the flasks were extracted with 1,1,1-trochloroethane. After concentrating the extraction products from the three flasks were compared with each other by thin layer chromatography (TLC) using silica gel plates and a 9: 1 chloroform / methanol solvent compared. For visual purposes the plates were coated with a mixture of anisaldehyde and sulfuric acid sprayed and then heated. With the product of the Flask in which β-ionone had been added to the fungal culture showed the TLC method the presence of the three substances in addition to ß-ionone. These substances were not contained in the extracts of the other two flasks. From this it was concluded that the three additional substances through a conversion of the ß-ionons, which by C. oxysporum fungus was caused. These three in addition The substances formed were all more polar than β-ionone, as were the Rf values in the TLC system showed: Substance I Rf 0.41 Substance II Rf 0.12 Substance III Rf 0.11 ß-Ionon Rf 0.64 Substances I, II and III were determined by a combination of columnar, high pressure liquid and thin layer chromatography and then separated by gas chromatography, mass spectrometry, nuclear magnetic resonance and infrared analysis identified. The following Identities established: substance I 2,6,6-trimethyl-1-cyclohexene-1-ethanol substance II 4-Hydroxy-2,6,6-trimethyl-1-cyclohexene-1-ethanol Substance III 2-hydroxymethyl-6,6-dimethyl-1-cyclohexene-1-ethanol.

Substance I is therefore compound A, substance II is compound B and Substance III the compound III.

Example 2 The procedure of Example 1 was repeated, but with a broth of the following composition: sucrose 3 g MgSO4 0.05 g K2HPO4 0.2 g NaNO3 0.2 g KH2PO4 0.1 g corn mix 1.0 g after the end of the incubation the presence of compounds A, B and C was determined.

Example 3 The procedure was as in Example 1, but using a broth of the following composition: Sucrose 5.0 g ges04 0.05 g K2HPO4 0.1 g NaNO3 0.2 g KCl 0.05 g yeast extract 0.1 g After completion After the incubation, the presence of compounds A, B and C was determined.

Example 4 2.5 l of a sterile malt extract broth in a 3 l fermentation vessel was inoculated with C. oxysporum and then with continuous stirring and aeration incubated at 280C. After 24 hours, 2.5 ml of β-ionone dissolved in Tween 80 were added. Incubation was then continued for an additional 160 hours, taking samples daily were taken. Analysis of these samples showed that the ß-ionone was gradually increasing with the progress of the incubation period and that the compounds disappeared A, B and C appeared gradually.

Example 5 The general procedure of Example 4 was repeated, however, using a 20 l container with 10 1 sterile Malt extract broth. 10 ml ß-Ionon in 40 ml Tween 80 were added and then became the broth was stirred at 400 rpm and an aeration of 6.0 l / min. 3.29 g of one Mixed product containing the compounds identified as compounds A, B and C. were extracted after a 160 hour incubation. The relative yields were: Compound A 330 mg Compound B 220 mg Compound C 40 mg Example 6 The procedure is followed as in Example 1, but using a pure culture of Abortiporus ciennis CBS 365.74 instead of C. oxysporum. At the end of the 7 day incubation period one found that compounds A, B and C were present.

Example 7 The procedure is as in Example 1, but using a pure culture of Beauveria bassiana CBS 209.27 instead of C. oxysporum. At the At the end of the 7-day incubation period, it was found that compounds A, B and C were present.

Example 8 The procedure is as in Example 1, but using a pure culture of Ophiobolus herpotrichus CBS 240.31 instead of C. oxysporum. At the end of the 7 day incubation period, the compounds were found to be A, B and C were present.

To the smoke-modifying properties of each of the compounds A, B and C determine, a panel of experts smoked cigarettes with a filling of smoked tobacco and cigarettes with an American style blended tobacco filling, each of which one of the compounds A to C had been added. The effect of the respective compound on tobacco smoke was compared to control cigarettes, which no smoke modifier had been added was checked. Each of the cigarettes released 9 mg of total particulate matter. Compounds A through C became added to the test cigarettes by means of a syringe in the form of an ethanolic solution and the loading levels were 200 ppm for Compound A and 500, respectively ppm for Compounds B and C. The control cigarettes received the same amount of ethanol, in which, however, nothing was dissolved. Both the test cigarettes and the control cigarettes were given 48 hours before smoking by the expert group stored.

The properties of the compounds to be tested were as follows: Compound A on smoked tobacco gave a smooth and rounded taste with a flower effect.

Compound A in blended tobacco gave a soft, sweetish nutty Grade.

Compound B in smoked tobacco gave an intense and with the Tobacco-friendly note and additionally a strong pine resin-like woody note and contributed to a fuller flavor.

Compound B in blended tobacco gave a sweet note and contributed to one full aroma.

Compound C in smoked tobacco enhanced the overall tobacco flavor with a flower-like Virginia note.

Compound-C in blended tobacco resulted in a spicy grassy, musty product Note and had a soft effect.

Claims (8)

Tobacco flavor modifiers and processes for their preparation PATENT CLAIMS Process for the preparation of a smoke flavor modifier, as a result, that ß-ionone can be mixed with a fungal culture in Brings contact and thereby at least a part of the ß-ionons with the formation of a Converted product, which at least one compound from the group consisting from compound A, compound B and compound C, which are in the description, respectively are defined, contains. 2. The method according to claim 1, characterized in that g e k e n n -z e i c h n e t that the compound A is extracted from the product for incorporation into the smoking material will. 3. Smoking material modifiers, thereby g e k e n n z e i c Not that it was produced by the method according to claim 1 or 2. 4. Smoke flavor modifiers, thereby g e -k e'n n z e i c h n e t that there is at least one compound from the group of compounds B and C contains. 5. Smoking material, thereby noting that it is a Smoke flavor modifier according to claims 3 or 4 contains. 6. Smoking material according to claim 5, characterized in that it is -k e n n z e i c h n e t that it is the agent in an amount of 5 to 2000 parts / million of the smoking material contains. 7. Smoking material according to claim 6, characterized in that it is -k e n n z e i c h n e t that there is a loading level in a range of 100 to 500 parts / million having. 8. Smoking articles, in that it is not indicated that it is a smoking material according to any one of claims 5 to 7.