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
  • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
  • A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
  • A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
  • A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/205—Heterocyclic compounds
  • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/40—Radicals substituted by oxygen atoms
  • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D319/02—1,2-Dioxanes; Hydrogenated 1,2-dioxanes
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Definitions

• the present invention relates to a novel compound of formula and to a process for its preparation.
• the said compound is defined as 5-(4-methyl-2-furyl)-6-methylheptan-Z-one.
• cigarettes for example, for the manufacture of cigarettes comprises a mixture of different types, to give the characteristic flavour and aroma desired in the smoke produced.
• cigarettes currently manufactured usually contain mixtures of Virginia, Maryland or Kentucky tobacco in combination with oriental or Turkish tobacco.
• flavouring substances and humectants as additives to these tobacco mixtures to further enhance the organoleptic properties thereof.
• the said compound may find a useful industrial application for the aromatisation of a great variety of materials, namely of foodstuffs and beverages.
• the said compound represents also a useful perfuming ingredient.
• 5-(4-methyl-2-furyl)-6-methyl-heptan-2-one in its pure form or in admixture with otherflavouring ingredients may be employed in a variety of forms.
• the chemical nature, solubility and stability determine the form in which the given compound or composition thereof is to be employed. It is preferable, however, to utilize the said compound or composition in the form of solutions thereof.
• the additive can be added at any step in the course of the treatment of the tobacco but it is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes or other products.
• a convenient method for flavouring tobacco consists in spraying the tobacco with an alcoholic solution of the compound or flavouring mixture. Combination 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.
• flavouring effects can be achieved with amounts ranging from 1 to 500 ppm, preferencially comprised between about 10 and 200 ppm, more particularly between about 10 and 20 ppm, based on the weight of the product flavoured.
• amounts ranging from 1 to 500 ppm, preferencially comprised between about 10 and 200 ppm, more particularly between about 10 and 20 ppm, based on the weight of the product flavoured.
• analogous proportions may be employed.
• the compound of the invention When used for the preparation of artificial flavour compositions, its proportions may be increased up to about percent by weight of the composition.
• the 5-(4-methyl-2-furyl)-6-methyI-heptan-2-one is a compound of natural origin. Said compound has been in fact isolated now for the first time from a natural essential oil.
• the essential oil has been obtained by extraction with a volatile solvent from the aqueous distillate collected by vapour distillation of Burley tobacco upon previous acidification of the said distillate to ca. pH 4.
• the isolation procedure mentioned above is particularly complex and uneconomical as the essential oil is obtained with a yield not higher than 0.03 percent by weight of the total tobacco treated.
• the isolation process consisted in a preliminary separation by fractional distillation under reduced pressure, whereupon the less volatile fractions [8. p. 35C/0.00l Torr] were subjected to several distillations by means of high fractionating power columns.
• the 5-(4-methyl-2-furyl)-6-methyl-heptan-2-one is merely a minor constituent of the essential oil. Said compound has been detected in a concentration of ca.
• ketone I in view of its flavouring and perfurning properties, ketone I possesses a clearly distinct field of application, said application being also wider than of the natural essential oil.
• Suitable basic agents include mineral or organic bases, such as, e.g., alkali metal hydroxides or alkoxides, or secondary or tertiary amines such as dimethylamine, triethylamine, pyridine, (1-, B- or 'y-picoline, piperidine or morpholine.
• Basic aluminium oxide may equally be employed.
• the conversion is preferably effected by absorption, on a column filled up with the basic agent, of a solution of compound II in an inert organic solvent.
• Suitable organic solvent include an aromatic hydrocarbon such as benzene or toluene.
• the final product is obtained by subsequent elution by means of a mixture of alcohol and ether, preferably a mixture of methanol or ethanol and diethyl ether. It is likely that the treatment with basic agent leads to the formation of an intermediate of formula III.
• Said compound may be in equilibrium with a hydroxy-dihydrofurance of formula IV as indicated below:
• the product directly issued from the previous treatment can be treated with an acid or basic dehydrating agent in order to give the furnaic compound of formula I.
• This dehydration can also be effected by means of heat.
• temperatures comprised between about 20c. and about 250C By operating at room temperature it has been possible to observe the formation of an appreciable amount of the final product.
• temperature higher than the room temperature preferably at temperatures comprised in the vicinity of 200C.
• Compound II used as starting material in the process of the invention, can be prepared by oxidation by means of singlet oxygen of solanone, also known under the name of 5-iso-propyl-8-methyl-nona-6,8-dien- 2-one.
• This compound can be synthesized according to known methods [cf. e.g.: J. Org. Chem. 30, 2918 (1965)].
• the oxidation by means of singlet oxygen can be promoted by means of a sensitized photooxygenation.
• Suitable sensitizers include conventional dyestuffs such as, e.g., porphyrines, methylene blue, eosin, chlorophil, Rose-Bengal or xanthene [cf.: Liebigs Ann. Chem. 674, 93 (1964); Angew. Chem. 69, 579 (1957)].
• Said photooxygenation can be carried out at temperatures near to or higher than 0c, preferably at room temperature.
• the photooxygenation can be effected in a protic medium, for instance in an alcoholic solution in methanol or ethanol, or in a solution of an aromatic hydrocarbon, such as benzene or toluene, an aliphatic hydrocarbon, such as n-hexane or cyclohexane, or an ether such as dioxane or tetrahydrofurane.
• a protic medium for instance in an alcoholic solution in methanol or ethanol, or in a solution of an aromatic hydrocarbon, such as benzene or toluene, an aliphatic hydrocarbon, such as n-hexane or cyclohexane, or an ether such as dioxane or tetrahydrofurane.
• Singlet oxygen can be obtained in accordance with one of the known chemical methods [see for example: C. S. Foote, Accounts of Chem. Research I, 104 (1968)].
• the peroxide used as starting material in the process described hereinabove can be prepared as follows:
• solanone in 200 ml methanol have been irradiated in the presence of 180 mg of Rose Bengal at 20 in a vessel destined to photochemical reactions by means of a mercury vapour lamp of 125 W (Type PHILIPS HPK). During the irradiation the solution was saturated with dry oxygen which was bubbled through at a rate of 80 ml/min.
• EXAMPLE 2 l g of a 1 percent solution of 5-(4-methyl-2-furyl)-6- methyl-heptan-Z-one in 95 percent ethanol was sprayed onto g ofa tobacco mixture of the american blend type.
• the tobacco thus flavoured was then used for the manufacture of test cigarettes the smoke of which was subjected to an organoleptic evaluation by a panel of flavour experts. These latter unanimously delcared that the smoke of the test cigarettes presented a typical character and a pleasant aroma of dry leaves when compared with the smoke of control cigarettes the tobacco of which was previously treated with 95 percent ethanol.
• the tobacco note of the flavoured cigarettes was also enhanced. The smoke of these cigarettes presented moreover a slightly fruity and flowery character.
• a tobacco product selected from the group consisting essentially of tobacco and tobacco substitutes which has added thereto of between about 1 to 500 ppm by weight of the flavouring compound consisting essentially of 5-(4-methyl-2-furyl)-6-methyl-heptan- 2-one which manifests the following formula:

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• General Health & Medical Sciences (AREA)
• General Chemical & Material Sciences (AREA)
• Toxicology (AREA)
• Wood Science & Technology (AREA)
• Nutrition Science (AREA)
• Food Science & Technology (AREA)
• Polymers & Plastics (AREA)
• Manufacture Of Tobacco Products (AREA)
• Dairy Products (AREA)
• Fats And Perfumes (AREA)

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4348066

Family Applications (1)

Country Status (4)

Citations (1)

• 1972
  • 1972-06-16 CH CH907572A patent/CH556645A/de not_active IP Right Cessation
• 1973
  • 1973-06-14 US US00370050A patent/US3857403A/en not_active Expired - Lifetime
  • 1973-06-15 DE DE2330517A patent/DE2330517A1/de active Pending
  • 1973-06-18 GB GB2890273A patent/GB1397897A/en not_active Expired

Patent Citations (1)

Also Published As

Similar Documents