US3840023A - Flavored tobacco composition - Google Patents
Flavored tobacco composition Download PDFInfo
- Publication number
- US3840023A US3840023A US00219136A US21913672A US3840023A US 3840023 A US3840023 A US 3840023A US 00219136 A US00219136 A US 00219136A US 21913672 A US21913672 A US 21913672A US 3840023 A US3840023 A US 3840023A
- Authority
- US
- United States
- Prior art keywords
- trimethyl
- tobacco
- cyclohex
- dien
- dione
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- 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
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
Definitions
- the present invention relates to compositions and a process for improving, enhancing or modifying the flavouring properties of foodstuffs, feedstuffs, beverages, pharmaceutical preparations and, more particularly, tobacco products.
- tobacco used for the preparation of cigarettes is composed essentially of a mixture of different types of tobacco which gives the characteristic flavour and aroma that is desired in the tobacco smoke produced.
- cigarettes currently manufactured usually contain mixtures of Virginia, Maryland or Kentucky tobacco in combination with oriental or Turkish tobacco.
- the flavor and aroma of tobacco smoke is improved by adding to the tobacco (which may be natural tobacco or a tobacco substitute of natural or synthetic origin) a flavouring composition containing atleast one compound selected from the following groups:
- Phenol derivatives a) Z-hydroxy-S-methyl-acetophenone 0.21. b) 2-methyl-5-isopropenyl-anisole Helv, Chim. Acta, 48,
- New compounds are identified by the abbreviation n.c.
- the results of the organoleptic evaluation tests are set out in the specific examples.
- An additional object of the present invention is to bacco substitutes comprising at least one compound selected from the groups listed above.
- the compounds and/or flavouring compositions described herein may be used in a variety of forms. It is preferable, however, to utilize these compounds or compositions in the form of solutions thereof.
- the chemical nature, solubility and stability determine the form in which a given compound or composition is to be employed.
- a convenient method for flavouring tobacco consists in spraying the tobacco with an alcoholic solution of the compound or flavouring mixture. Combinations of solvents such as alcohol and propylene glycol may also be used.
- a further object is to provide a process for the preparation of a new cyclic ketone the 4,4,6-trimethylcyclohexa-2,5-dien-2-ol-l-one.
- the process comprises treating isophorone with a halogenating agent, such as for example N-bromosuccinimide, to afford a 3,5,5- trimethyl-4-halocyclohex-2-en- 1 -one, and oxidizing the ketone thus obtained by means of a tertiary amine oxide, such as trimethylamine oxide.
- the present invention relates further to the new compounds which have been listed above.
- Said compounds may be prepared in accordance with the methods described hereinbelow: 2. b) 3,5,5-Trimethyl-2,3-epoxy-cyclohexane-l,4-
- dione 2 ml of a 6N aqueous solution of NaOH have been added during a period of 15 minutes at 15 C to a mixture of 3,5,5-trimethyl-cyclohex-2-en-l ,4-dione (3.7 g) and hydrogen hydroperoxide (8.3 ml of a 30 percent solution) in 27 ml of methanol.
- the mixture was kept under stirring during 3 hours at 20-25 C, treated with water and extracted with ether.
- the combined organic extracts were washed with water until neutrality, dried over MgSO and evaporated.
- Ketal (b) has been reduced by LiAll-l, in ether solution and the product thus obtained directly hydrolysed in a mixture of dioxane and 5 percent H at 20C.
- 3,5,5-trimethyl-4- methylene-cyclohex-Z-en-1-one and 3,5,5-trimethyl-1 try, particularly for modifying the roasted character of 35 the taste of certain beverages such as infusions or decoctions prepared from tea, coffee, lime-blossom tea.
- said compounds can also impart to the products to which they are added a caramelor straw-like character and find a useful application in the flavouring of infusions or decoctions and certain fermented foodstuffs in general.
- Example 1 7 g of a 1 percent alcoholic solution of 3,5,5-
- cent ethyl alcohol were sprayed onto a mixture of tobacco of american blend (100 g).
- tobacco thus lflavoured was used to manufacture test cigarettes, ;'the smoke of which was then subjected to organoleptic evaluation by comparison with non flavoured cigarettes above mentioned compounds has been described in The panel of experts unanimou sly defined the taste of the test cigarettes as being sweeter than that of the control cigarettes; moreover, the smoke possessed a note with an improved herb-like character and was pronounced of the taste of cigar smoke.
- Example 2 a A mixture of isophorone (13.82 g; 0.1 Mole) and N-bromo-succinimide (17.80 g; 0.1 Mole) in the presence of traces of 01,0:'-azodiisobutyronitrile was refluxed in 500 ml of CCl.; during 15 minutes. 500 ml of petrol-ether (3050C) were then added to the cool reaction mixture and the succinimide thus precipitated was filtered off. By evaporating the volatile components of the clear filtrate, crude 3,5,5-trimethyl-4- bromo-cyclohex-Z-en-l-one was obtained.
- test A (control) B C p-ethylguaiacol 1% l0 10 20 guaiacol 1% 15 15 30 3,5,5-trimethyl-cyclohexane- 1,4-dione 10% 30 30 ethyl alcohol 975 945 920 1000 1000 1000 in 95% ethyl alcohol
- Flavours A, B and C were then compared in a concentration of 0.06 g of flavour for 60 ml of sugar syrup (prepared by dissolving 650 g of sucrose in 1350 ml of water).
- compositions were tested by a panel of qualified tasters who expressed their views on the value of the flavours used for their preparation. These persons declared unanimously that the taste of the syrup which had been flavoured with composition B had a more diffuse note than the syrup flavoured with composition A; moreover, the typical phenolic character shown by this latter syrup was well masked. By using composition C, analogous results were obtained although less pronounced.
- Flavours A, B and C were then compared in a concentration of 0.06 g of flavour for 60 ml of salt solution (prepared by dissolving 0.5 g of NaCl in ml of water).
- Example 4 The following flavouring compositions were pre- -PEEQ PYELJPWRHEZISPX e ht in 95% ethyl alcohol The above given flavours were then compared in a sugar syrup and in salt aqueous solution exactly as indicated in Example 3.
- a process for improving, enhancing, or modifying the organoleptic properties of a tobacco product which comprises adding thereto about 1 to about 1000 parts per million based on the weight of tobacco of a compound selected from the group consisting of:
- a tobacco or tobacco product having added thereto about 1 to about 1,000 parts per million based on the weight of tobacco of a compound selected from the group consisting of:
- a process for improving, enhancing, or modifying the organoleptic properties of a tobacco product which comprises adding thereto about 1 to about 1,000 parts per million based on the weight of tobacco of 4,4- ,6-trimethyl-cyclohexa-2,5-dien-2-ol-l-one.
Abstract
Various compounds are disclosed to be useful in the flavouring of tobacco products. Many of said compounds are also useful as odoriferous ingredients and/or as flavouring agents in general for foodstuffs, beverages and pharmaceutical preparations. The flavorants employed are added to the tobacco in amounts of less than 1000 parts per million and are cyclo-aliphatic derivatives of which 4,4,6-trimethyl-cyclohexa-2,5-dien-2-ol-1-one is a preferred example.
Description
rte States Patent 1 1 [111 3,340,023 emole Oct. 8, 1974 [54] FLAVORED TOBACCO COMPOSITION 3,746,010 8/1973 Leffingwell 131/144 [75] Inventor: Edouard P. Demole, Geneva,
Switzerland Primary Examiner-Melvin D. Rein [73} Assignee: Firmenich SA. Geneva Attorney, Agent, or Firm-Penme & Edmonds Switzerland 1 [22] Filed: Jan. 19, 1972 [57] ABSTRACT [2]] Appl. No.: 219,136 Various compounds are disclosed to be useful in the flavouring of tobacco products. Many of said com- [52] us. C]. 131/17 131/144 426/175 pounds are also useful as odoriferous ingredients and- 260/586 /or as flavouring agents in general for foodstuffs, bev- [51] Int Cl A24) 15/04 erages and pharmaceutical preparations. The flavor- [58] Field of Search 15 17 ants employed are added to the tobacco in amounts of less than 1000 parts per million and are cycloaliphatic derivatives of which 4,4,6-trimethyl- [56] References Cited cyclohexa-2,5-dien-2-ol-l-one is a preferred example.
UNITED STATES PATENTS 4 Claims, No Drawings 3,559,656 2/l97l Heckman l3l/l44 9rmula inslsds:
1 FLAVORED TOBACCO COMPOSITION DESCRIPTION OF THE INVENTION The present invention relates to compositions and a process for improving, enhancing or modifying the flavouring properties of foodstuffs, feedstuffs, beverages, pharmaceutical preparations and, more particularly, tobacco products.
It is well known that tobacco used for the preparation of cigarettes, for example, is composed essentially of a mixture of different types of tobacco which gives the characteristic flavour and aroma that is desired in the tobacco smoke produced. Thus, cigarettes currently manufactured usually contain mixtures of Virginia, Maryland or Kentucky tobacco in combination with oriental or Turkish tobacco.
The respective proportions of the various types of to bacco are varied in order to obtain the particular flavour and aroma desired. It is also common practice to employ flavouring substances and humectants as additives to these tobacco mixtures to further enhance the organoleptic properties thereof.
Accordingly, it is an object of the present invention to provide a process for improving, enhancing or modifying the organoleptic properties of a tobacco product by incorporating therein an aromatic composition or certain synthetic flavouring agents.
The flavor and aroma of tobacco smoke is improved by adding to the tobacco (which may be natural tobacco or a tobacco substitute of natural or synthetic origin) a flavouring composition containing atleast one compound selected from the following groups:
s. QQQIIPL L wherein R and R represent an alkyl radical comprising one to six carbon atoms, or a hydrogen atom.
Specific examples of the compounds comprised by epoxy-B-ionone 6-methyI-hepta-3,S-dien-Z-one 3-isopropyl-cyclopent-2-en- I -one octa-3,5-dien-2-one nonane2,5 ,8-trione 2-methyl-5-(a-methyl-a-hydroxy-ethyl a) 2,5-dimethyI-4,5-dihydrofuran Swiss patent No. 474,500
-oI-4-one b) 2,5-dimethyI-4,S-dihydrothio- 0.0.5. No. 1,932,800
phen-3-ol-4-one c) Z-methyl-S-ethyl-4,5-dihydrofu- Swiss patent No. 491,904
ran-3-ol-4-one d) 2-ethyl-5-methyI-4,5-dihydrofu- Swiss patent No. 491,904
ran-3-ol-4-one e) 2,5-dimethyl-2,3-dihydrofuranl-lelwflhim cta,
3-one 46,1259( 1963) 5. Caryophyllene derivatives:
a) caryophyllenepoxide of formula Helv. Chim. Acta, 61, 494 (1968) i b) and c) caryophyllene alcohols of formula and OH Helv. Chim. Acta, 61, 494 (1968) 9-. Mis el an o s V Helv.Chim.Acta, 29,1829 (1946) USSR patent No. 138,6l2 J.Org.Chem., 33, I656 (I968) Belgian patent No. 660,099
Ben, 76, 183 (1943) Ben, 38, 1719 (1905) cyclohex-2-en- I -one 4-methylthiobutan-2-one a) N-isoamylacetamide Ben, 58, 2,017 (I925) b) N-isoamylformamide Compt. rend,, 176, l,l59 (1923) 2. Cycloaliphatic derivatives: a) 3,5,5-trimethyl-cyclohex-2-em4-ol- Tetrahedron, Suppl. 8 Part l-one I, p. I (I966) b) 3,5,5-trimethyl-2,3-epoxy-cyclon.c.
hexane-1,4-dione c) 2,6,6-trimethyl-cycIohex-2-en-4-oln.c
l-one d) 4,4,6-trimethyl-cyclohexa-2,5-dienn.c
2-ol-l-one e) 3,5,5-trimethyl-cycIohex-3-en-l-yl n.c
acetate f) 3,5,5-trimethyl-4-hydroxy-4-[but-l- J. Org.Chem., 33, 3566 en-3-one]-cycIohex-2-en-1-one (1968) g) 3,5,5-trimethyl-2-hydroxy-cyclohex- Phytochemistry, I0, 2755 2-ene-l,4-dione (l97l) h) 3,5,5-trimethyl-cyclohex-2-en-2-ol- J.Org.Chem. 24, 719
l-one (I966) 3. Phenol derivatives: a) Z-hydroxy-S-methyl-acetophenone 0.21. b) 2-methyl-5-isopropenyl-anisole Helv, Chim. Acta, 48,
4. I-Ieterocyclic ketones of formula course of this description or in one of the examples.
New compounds are identified by the abbreviation n.c. The results of the organoleptic evaluation tests are set out in the specific examples.
An additional object of the present invention is to bacco substitutes comprising at least one compound selected from the groups listed above.
C.A., 52, 9l4le (I958) The compounds listed above have been divided into groups based more on similarities of their chemical structure than on their specific organoleptic properties. The wide range of organoleptic properties associated with the compounds described above makes it possible to achieve a variety of effects depending on the nature of the individual components used in a given aromatic mixture.
The compounds and/or flavouring compositions described herein may be used in a variety of forms. It is preferable, however, to utilize these compounds or compositions in the form of solutions thereof. The chemical nature, solubility and stability determine the form in which a given compound or composition is to be employed.
' A convenient method for flavouring tobacco consists in spraying the tobacco with an alcoholic solution of the compound or flavouring mixture. Combinations of solvents such as alcohol and propylene glycol may also be used.
The proportions of the new compounds to be used in said compositions or in accordance with the process of the present invention can vary within wide limits. Said proportions depend particularly on the specific organoleptic effects it is desired to achieve and on the origin of the tobacco products to which the mentioned flavouring ingredients are added. For instance, interesting flavouring effects can be achieved with amounts ranging from 1 to 1,000 ppm, based on the weight of the product flavoured. However, special effects may be achieved by proportions as high as or even percent. Typically, proportions comprised in between about 10 and 200 ppm are preferably used.
in all cases, the ranges given above may be varied, depending upon the specific odoriferous or flavouring effect it is desired to achieve.
A further object is to provide a process for the preparation of a new cyclic ketone the 4,4,6-trimethylcyclohexa-2,5-dien-2-ol-l-one. The process comprises treating isophorone with a halogenating agent, such as for example N-bromosuccinimide, to afford a 3,5,5- trimethyl-4-halocyclohex-2-en- 1 -one, and oxidizing the ketone thus obtained by means of a tertiary amine oxide, such as trimethylamine oxide.
The above mentioned process is better illustrated by 45 i l? ,f9ll9uinsrsa i ui.
halogenation logen RaN O R=alkyl ceed through a quaternary salt intermediate having the formula to yield as final product a cyclohexane-l ,4-dione. We have unexpectedly found that by the oxidation of 3,5,5- trimethyl-4-halocyclohex-2-en-l-one, in accordance with the process of the present invention, a l,2-dione derivative was formed instead. Said diketone was in equilibrium with its keto-enol form according to the above given scheme.
The present invention relates further to the new compounds which have been listed above.
Said compounds may be prepared in accordance with the methods described hereinbelow: 2. b) 3,5,5-Trimethyl-2,3-epoxy-cyclohexane-l,4-
. dione 2 ml of a 6N aqueous solution of NaOH have been added during a period of 15 minutes at 15 C to a mixture of 3,5,5-trimethyl-cyclohex-2-en-l ,4-dione (3.7 g) and hydrogen hydroperoxide (8.3 ml of a 30 percent solution) in 27 ml of methanol. The mixture was kept under stirring during 3 hours at 20-25 C, treated with water and extracted with ether. The combined organic extracts were washed with water until neutrality, dried over MgSO and evaporated.
3.3 3g (81.5 percent) of the desired product, b.p. 40C/0.00l Torr, were thus obtained.
IR 1715 cm; MS M 168; m/e: 56
NMR(CC1.,) 1.05 (3l-l,s); 1.25 (3l-l,s); 1.50 (3l-l,s);
2.08 (ll-[,d, J =13 cps); 3.09 (lll,d, J =13 cps); 3.47 (ll-[,s) 8 ppm. 3,5,5-Trimethyl-cyclohex-2-en-l,4-dione, used as starting material for the above described preparation, may be obtained in accordance with the procedure de scribed in Tetrahedron, Suppl. 8, Part I, p. l (1966). 2. c) 2,6,6-Trimethyl-cyclohex-2-en-4-ol-l-one Prepared in accordance with the procedure described in Tetrahedron, Suppl. 8, Part. I. p. l (1966), starting from isophorone.
In addition to the ketal intermediate of formula which has been separated by column chromatography on silicagel (elution: benzene ethyl acetate).
Ketal (b) has been reduced by LiAll-l, in ether solution and the product thus obtained directly hydrolysed in a mixture of dioxane and 5 percent H at 20C.
NMR (CCl 1.10 (6H,s); 1.72 (3H,s); 1.85-2.40
m); 4.50 (2H, s broad); 6.64 (1H, s broad) 8 ppm. 2. d) 4,4,6-Trimethyl-cyclohexa-2,5-dien-2-ol-l-one Prepared according to Example 2. 2. e) 3,5,5-Trimethyl-cyclohex-3-en-l-yl acetate Prepared by reduction by means of sodium borohydride in methanol of B-isophorone [obtained according to J. Am. Chem. Soc., 63, 2308 (1941)] and subsequent acetylation of the obtained 3,5,5-trimethylcyclohex-3-en-1-ol by means of acetic anhydride in the presence of sodium acetate at 50 C during hours. NMR (CC1.,) 1.0 (6H,s); 1.62 (3l-l,s); 1.92 (3H,s);
5.10 (ll-[,s); 4.6-5.2 (1H,m) 8 ppm There also may be accomplished the modifying, im-.
proving or enhancing the organoleptic properties of foodstuffs, feedstufis, beverages and pharmaceutical preparations, which comprises adding to said materials a small but effective quantity of at least one compound selected from the class consisting of group 2 and the dione, 2,2,6-trimethyl-cyclohexan-4-ol l-one, 3,5,5- trimethyl-cyclohexan-4-ol-l-one,
cyclohexane-l,4-dione. The preparation of the herein- U.S. Pat. Letter No. 3,380,456.
We have surprisingly found that whenever said compounds were incorporated to said materials or to flavouring compositions containing among their ingredients phenol or phenol derivatives, the harshness and.
3,5,5-trimethyl-4- methylene-cyclohex-Z-en-1-one and 3,5,5-trimethyl-1 try, particularly for modifying the roasted character of 35 the taste of certain beverages such as infusions or decoctions prepared from tea, coffee, lime-blossom tea.
Moreover, their use is particularly interesting for the Compound Amount [g]" I Caramel and c) as above flavouring of meat, more specifically of smoked meat,
of roasted cereals and roasted nuts. When taken separately, said compounds can also impart to the products to which they are added a caramelor straw-like character and find a useful application in the flavouring of infusions or decoctions and certain fermented foodstuffs in general.
The proportions previously indicated for tobacco flavouring equally apply for the use of the above compounds in accordance with the hereinabove described method. For the purpose of the present specification, the term foodstuff is used broadly; and it is deemed to indicate also products such as coffee, tea and cocoa.
The invention is better illustrated by the following examples.
Example 1 7 g of a 1 percent alcoholic solution of 3,5,5-
20 i trimethyl-2,3-epoxy-cyclohexane- 1 ,4-dione (in 95 perfollowing group: 3 ,5 ,5-trimethyl-cyclohex-2-ene-1 ,4-
cent ethyl alcohol) were sprayed onto a mixture of tobacco of american blend (100 g). The tobacco thus lflavoured was used to manufacture test cigarettes, ;'the smoke of which was then subjected to organoleptic evaluation by comparison with non flavoured cigarettes above mentioned compounds has been described in The panel of experts unanimou sly defined the taste of the test cigarettes as being sweeter than that of the control cigarettes; moreover, the smoke possessed a note with an improved herb-like character and was reminiscent of the taste of cigar smoke.
By following the same procedure as that given in above Example 1, other samples were evaluated. The hereinbelow table gives the list of the tested compounds as well as the quantities employed and the flavour effect observed TABLE Organoleptic Evaluation Nutty, chocolate taste Rich nutty taste; sweet flue-cured character; chocolate; adds body note; more pleasant Rich sweet, nutty taste; adds flue-cured character Phenolic taste; slight Burley effect Sweet, slightly woody, caramel and honey-like Fruity, woody, slightly sulphur-like Sweet, caramel Sweet, caramel Woody, cigar smoke-like; orient tobacco note Sweet, nutty, chocolate taste; adds body; some flue-cured character Sweet, nutty, chocolate taste; adds body Sweet, green note Adds body; flue-cured flavour note Sweet. nutty, chocolate taste; some flue-cured character Flue-cured character. phenolic; nutty, chocolate taste; adds body Some Burley character The amounts indicated refer to the quantities of a l% alcoholic solution ethyl alcohol) The characters given refer to specific flavour properties of the tested compounds on tobacco as compared with a non flavoured tobacco. The amount indicated refers to the quantities of a 2% alcoholic solution (95% ethyl alcohol).
Example 2 a. A mixture of isophorone (13.82 g; 0.1 Mole) and N-bromo-succinimide (17.80 g; 0.1 Mole) in the presence of traces of 01,0:'-azodiisobutyronitrile was refluxed in 500 ml of CCl.; during 15 minutes. 500 ml of petrol-ether (3050C) were then added to the cool reaction mixture and the succinimide thus precipitated was filtered off. By evaporating the volatile components of the clear filtrate, crude 3,5,5-trimethyl-4- bromo-cyclohex-Z-en-l-one was obtained.
NMR (CCl 1.16 (311,5); 1.25 (3l-l,s); 2.11 (3I-l,s); 2.07 (1l-l,d, .1 =16 cps); 2.53 (1l-l,d, J =16 cps); 4.45 (ll-1,5); 5.78 (ll-Ls) 8 ppm.
b. During a period of 30 minutes 3,5,5-trimethyl-4- bromo-cyclohex-2-en-1 -one (43.4 g) was added to a solution kept at 40C of anhydrous trimethylamine N- oxide (32 g) in 100 ml of anhydrous chloroform. The reaction was slightly exothermic and the temperature of the mixture was kept at 45-50C by external cooling during the whole addition. After cooling to room temperature, said mixture was poured onto 110 ml of 10 percent H SO and the organic layers which separated were washed with water (3 X), a 10 percent solution of sodium carbonate (3 X) and finally with water again (3 X) until neutralisation.
By evaporation of the volatile components, and subsequent distillation of the resulting residue a product was obtained at b.p. 4760C/0.001 Torr. This product was treated with petrol-ether (30- 50 C) and then successively washed with a 5 percent aqueous solution of sodium carbonate (2 X) and a 2 percent aqueous solution of NaOH (5 X). The mother liquors were acidified and immediately extracted with diethyl ether.
The combined extracts were washed, dried over MgSO and evaporated at reduced pressure. 8 g of the desired product were thus obtained (95 percent purity). The subsequent purification was carried out by sublimation at 70-80 C/10 Torr, and yielded 6 g of pure 4,4,6-trimethyl-cyclohexa-2,5-dien-2-ol-1-one. The product had a positive test when treated with a solution of ferric chloride (blue-violet colour); m.p. 46 C.
IR (CCl 1630, 1650, 3440 cm However, under other conditions it is reasonable to assume that the keto-enol equilibrium may be in favour of a diketonic structure according to the following q2 9i1= r l l 2 H0 0 keto-enol diketone Example 3 The following flavouring compositions were prepared by admixing (parts by weight):
(test) A (control) B C p-ethylguaiacol 1% l0 10 20 guaiacol 1% 15 15 30 3,5,5-trimethyl-cyclohexane- 1,4-dione 10% 30 30 ethyl alcohol 975 945 920 1000 1000 1000 in 95% ethyl alcohol Flavours A, B and C were then compared in a concentration of 0.06 g of flavour for 60 ml of sugar syrup (prepared by dissolving 650 g of sucrose in 1350 ml of water).
The finished syrups were tested by a panel of qualified tasters who expressed their views on the value of the flavours used for their preparation. These persons declared unanimously that the taste of the syrup which had been flavoured with composition B had a more diffuse note than the syrup flavoured with composition A; moreover, the typical phenolic character shown by this latter syrup was well masked. By using composition C, analogous results were obtained although less pronounced.
Flavours A, B and C were then compared in a concentration of 0.06 g of flavour for 60 ml of salt solution (prepared by dissolving 0.5 g of NaCl in ml of water).
In this case also the flavour experts declared that the taste of the beverages which had been flavoured with compositions B and C lacked the phenolic character of the beverage flavoured with composition A.
Example 4 The following flavouring compositions were pre- -PEEQ PYELJPWRHEZISPX e ht in 95% ethyl alcohol The above given flavours were then compared in a sugar syrup and in salt aqueous solution exactly as indicated in Example 3. The flavour experts declared I claim:
1. A process for improving, enhancing, or modifying the organoleptic properties of a tobacco product, which comprises adding thereto about 1 to about 1000 parts per million based on the weight of tobacco of a compound selected from the group consisting of:
a. 3,5,5-trimethyl-cyclohex-2-en-4-ol- 1 -one b. 3,5,5-trimethyl-2,3-epoxy-cyclohexanel ,4-dione c. 2,6,6-trimethyl-cyclohex-2-en-4-ol- 1 -one d. 4,4,6-trimethylcyclohexa-2,5-dien-2-ol- 1 -one e. 3,5,S-trimethyl-cyclohex-3-enl -yl acetate f. 3 ,5 ,5 -trimethyl-4-hydroxy-4-( but- 1 -en-3-one cyclohex-2-enl-one 1 3,5,5-tr1methyldione h. 3,5,5-trimethyl-cyclohex-2-en-2-oli -one.
2. A tobacco or tobacco product having added thereto about 1 to about 1,000 parts per million based on the weight of tobacco of a compound selected from the group consisting of:
a. 3,5 ,5-trimethyl-cyclohex-2-en-4-ol- 1 -one b. 3,5 ,5-trimethyl-2-3,-epoxy-cyclohexanel ,4-dione c. 2,6,6-trimethyl-cyclohex-2-en-4-ol- 1 -one d. 4,4,6-trimethyl-cyclohexa-2,5-dien-2-ol- 1 -one e. 3,5,5-trimethyl-cyclohex-3-en-l-yl acetate f. 3 ,5,5-trimethyl-4-hydroxy-4-(hydroxy-4-( but- 1 -en- 3-one)-cyclohex-2-en-l-one 3,5,S-trimethyl-2-hydroxy-cyclohex-2-ene-l ,4-
dione h. 3,5,5-trimethyl-cyclohex-2-en-2-ol- 1 -one.
3. A process for improving, enhancing, or modifying the organoleptic properties of a tobacco product, which comprises adding thereto about 1 to about 1,000 parts per million based on the weight of tobacco of 4,4- ,6-trimethyl-cyclohexa-2,5-dien-2-ol-l-one.
4. A tobacco or tobacco product having added thereto about 1 to about 1000 parts per million based on the weight of tobacco of 4,4,G-trimethyl-cyclohexa- 3,5,5-trirnethyl-2-hydroxy-cyclohex-2-ene lg
Claims (4)
1. A PROCESS FOR IMPROVING, ENHANCING, OR MODIFYING THE ORGANOLEPTIC PROPERTIES OF A TOBACCO PRODUCT, WHICH COMPRISES ADDING THERETO ABOUT 1 TO ABOUT 1000 PARTS PER MILLION BASED ON THE WEIGHT OF TOBACCO OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF: A. ,5,5-TRIMETHYL-CYCLOHEX-2-EN-4-OL-1-ONE B. 3.5.5-TRIMETHYL-2,3-EPOXY-CYCLOHEXANE-1,4-DIONE C. 2.6.6-RIMETHYL-CYCLOHEX-2-EN-4-L-1-ONE D. 4.4,6-TRIMETHYL-CYCLOHEXA-2,5-DIEN-2-OL-1-ONE E. 3,5,5-TRIMETHYL-CYCLOHEXA-2,5-DIEN-2-OL-1-ONE F. 3,55-TRIMETHYL-4-HYDROXY-4-(BUT-1-EN-3-ONE)-CYCLOHEX2-EN-1-ONE G. 3,5,5-TRIMETHYL-2-HYDROXY-CYCLOHEX-2-ENE-1,4-DIONE H. 3,5,5-TRIMETHYL-CYCLOHEX-2-EN-2-OL-1-ONE.
2. A tobacco or tobacco product having added thereto about 1 to about 1,000 parts per million based on the weight of tobacco of a compound selected from the group consisting of: a. 3,5,5-trimethyl-cyclohex-2-en-4-ol-1-one b. 3,5,5-trimethyl-2-3,-epoxy-cyclohexane-1,4-dione c. 2,6,6-trimethyl-cyclohex-2-en-4-ol-1-one d. 4,4,6-trimethyl-cyclohexa-2,5-dien-2-ol-1-one e. 3,5,5-trimethyl-cyclohex-3-en-1-yl acetate f. 3,5,5-trimethyl-4-hydroxy-4-(hydroxy-4-(but-1-en-3-one)-cyclohex-2-en-1-one g. 3,5,5-trimethyl-2-hydroxy-cyclohex-2-ene-1,4-dione h. 3,5,5-trimethyl-cyclohex-2-en-2-ol-1-one.
3. A process for improving, enhancing, or modifying the organoleptic properties of a tobacco product, which comprises adding thereto about 1 to about 1,000 parts per million based on the weight of tobacco of 4,4,6-trimethyl-cyclohexa-2,5-dien-2-ol-1-one.
4. A tobacco or tobacco product having added thereto about 1 to about 1000 parts per million based on the weight of tobacco of 4, 4,6-trimethyl-cyclohexa-2,5-dien-2-ol-1-one.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00219136A US3840023A (en) | 1972-01-19 | 1972-01-19 | Flavored tobacco composition |
US05/482,557 US3957061A (en) | 1972-01-19 | 1974-06-24 | Aromatic compositions |
US482776A US3920027A (en) | 1971-01-19 | 1974-06-24 | Flavored tobacco product |
US05/586,368 US4092989A (en) | 1971-01-19 | 1975-06-12 | Aromatic compositions |
US05/586,310 US4029106A (en) | 1971-01-19 | 1975-06-12 | Aromatic compositions |
US05/586,382 US4029107A (en) | 1971-01-19 | 1975-06-12 | Aromatic compositions |
US05/586,384 US4031902A (en) | 1971-01-19 | 1975-06-12 | Aromatic compositions |
US05/586,383 US4029108A (en) | 1971-01-19 | 1975-06-12 | Aromatic compositions |
US05/586,386 US4014350A (en) | 1971-01-19 | 1975-06-12 | Aromatic compositions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00219136A US3840023A (en) | 1972-01-19 | 1972-01-19 | Flavored tobacco composition |
Related Child Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US482776A Division US3920027A (en) | 1971-01-19 | 1974-06-24 | Flavored tobacco product |
US05/482,557 Division US3957061A (en) | 1972-01-19 | 1974-06-24 | Aromatic compositions |
US05/482,512 Division US3989857A (en) | 1971-01-19 | 1974-06-24 | Flavoring phenol or phenol derivative containing food or feed with cycloaliphatic derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
US3840023A true US3840023A (en) | 1974-10-08 |
Family
ID=22818025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00219136A Expired - Lifetime US3840023A (en) | 1971-01-19 | 1972-01-19 | Flavored tobacco composition |
Country Status (1)
Country | Link |
---|---|
US (1) | US3840023A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3903900A (en) * | 1973-05-14 | 1975-09-09 | Int Flavors & Fragrances Inc | Tobacco articles and compositions containing 1,2-cyclohexanedione and methods for producing same |
US3915175A (en) * | 1974-02-12 | 1975-10-28 | Firmenich & Cie | Flavored tobacco composition |
US3929676A (en) * | 1974-08-02 | 1975-12-30 | Int Flavors & Fragrances Inc | Bicyclic fragrance materials and processes therefor |
US3967629A (en) * | 1973-10-01 | 1976-07-06 | International Flavors & Fragrances Inc. | Bicyclic fragrance materials and processes therefor |
US3975441A (en) * | 1973-05-07 | 1976-08-17 | Teijin Limited | Process for recovering purified 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadiene-1-one |
US3989857A (en) * | 1971-01-19 | 1976-11-02 | Firmenich S.A. | Flavoring phenol or phenol derivative containing food or feed with cycloaliphatic derivatives |
US4014350A (en) * | 1971-01-19 | 1977-03-29 | Firmenich S.A. | Aromatic compositions |
US4092989A (en) * | 1971-01-19 | 1978-06-06 | Firmenich S.A. | Aromatic compositions |
US5167955A (en) * | 1991-05-17 | 1992-12-01 | The Research Foundation Of State University Of New York | New aggregation pheromone for the bark beetle Ips pini and uses thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3559656A (en) * | 1969-04-28 | 1971-02-02 | Reynolds Tobacco Co R | Tobacco product |
US3746010A (en) * | 1972-08-11 | 1973-07-17 | Reynolds Tobacco Co R | Tobacco product |
-
1972
- 1972-01-19 US US00219136A patent/US3840023A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3559656A (en) * | 1969-04-28 | 1971-02-02 | Reynolds Tobacco Co R | Tobacco product |
US3746010A (en) * | 1972-08-11 | 1973-07-17 | Reynolds Tobacco Co R | Tobacco product |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4029106A (en) * | 1971-01-19 | 1977-06-14 | Firmenich S.A. | Aromatic compositions |
US3989857A (en) * | 1971-01-19 | 1976-11-02 | Firmenich S.A. | Flavoring phenol or phenol derivative containing food or feed with cycloaliphatic derivatives |
US4014350A (en) * | 1971-01-19 | 1977-03-29 | Firmenich S.A. | Aromatic compositions |
US4029107A (en) * | 1971-01-19 | 1977-06-14 | Firmenich S.A. | Aromatic compositions |
US4029108A (en) * | 1971-01-19 | 1977-06-14 | Firmenkh Sa | Aromatic compositions |
US4031902A (en) * | 1971-01-19 | 1977-06-28 | Firmenich S.A. | Aromatic compositions |
US4092989A (en) * | 1971-01-19 | 1978-06-06 | Firmenich S.A. | Aromatic compositions |
US3975441A (en) * | 1973-05-07 | 1976-08-17 | Teijin Limited | Process for recovering purified 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadiene-1-one |
US3903900A (en) * | 1973-05-14 | 1975-09-09 | Int Flavors & Fragrances Inc | Tobacco articles and compositions containing 1,2-cyclohexanedione and methods for producing same |
US3967629A (en) * | 1973-10-01 | 1976-07-06 | International Flavors & Fragrances Inc. | Bicyclic fragrance materials and processes therefor |
US3915175A (en) * | 1974-02-12 | 1975-10-28 | Firmenich & Cie | Flavored tobacco composition |
US3929676A (en) * | 1974-08-02 | 1975-12-30 | Int Flavors & Fragrances Inc | Bicyclic fragrance materials and processes therefor |
US5167955A (en) * | 1991-05-17 | 1992-12-01 | The Research Foundation Of State University Of New York | New aggregation pheromone for the bark beetle Ips pini and uses thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4364400A (en) | Heterocyclic derivatives as flavoring agents | |
US3989857A (en) | Flavoring phenol or phenol derivative containing food or feed with cycloaliphatic derivatives | |
US3840023A (en) | Flavored tobacco composition | |
US4014350A (en) | Aromatic compositions | |
US3914227A (en) | Certain cycloalkyl pyrazinyl ketones | |
US3380456A (en) | Tobacco product | |
US3885051A (en) | Flavoring and aromatising with 3-acetyl-2,5-dialkyl furans or thiophenes | |
US3937228A (en) | Aromatic compositions | |
US4071034A (en) | 2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of tobacco using one or more of said pyrans | |
US4224351A (en) | Flavoring with certain sulphur compounds | |
US3957061A (en) | Aromatic compositions | |
US3983885A (en) | Aromatic compositions | |
US3903900A (en) | Tobacco articles and compositions containing 1,2-cyclohexanedione and methods for producing same | |
US4092989A (en) | Aromatic compositions | |
US3890981A (en) | Novel process for altering the organoleptic properties of tobacco using one or more alpha-pyrones and process | |
US3892809A (en) | Process for the preparation of butenoyl 1,3-cyclohexadienes | |
US3981311A (en) | Aromatic compositions | |
US3875307A (en) | Flavoring foodstuffs with a mixture containing 1,2 cyclohexanedione | |
US4115406A (en) | 2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of foodstuffs and tobacco using one or more of said pyrans | |
US3782391A (en) | {62 -methylvaleric acid alkyl esters as tobacco flavorants | |
DE2458639C3 (en) | Tobacco products with an additive that changes taste or aroma | |
US3126012A (en) | Smqeong tobacco additives in the form | |
US4011245A (en) | Method for the manufacture of 2,6,10,10-tetramethyl-1-oxaspiro 4,5-dec-6-ene | |
US4128101A (en) | Tobacco compositions containing 3-ethoxy-4-hydroxybenzaldehyde 2,2-dimethyl propanediol acetal | |
US3884247A (en) | Tobacco compositions employing flavoring agents comprising unsaturated butyrolactone derivatives and precursors thereof |