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

Definitions

• ABSTRACT Described is a tobacco product having added thereto an amount sufficient to alter the flavor or aroma of the tobacco product particularly on smoking, of one 1 or more alpha-pyrone compounds having the generic structure:
• R is methyl or hydrogen, and R is C3-C5 alkyl; processes for producing such tobacco products; and flavor formulations for use in conjunction with tobacco products containing one or more of such alphapyrones.
• Sweet, aromatic, warm, spicy, maple-like, fruity, coumarin-like, vanillin-like, lactone, lovage-like, celery-like and nut-like notes are particularly desirable for many uses concerning the flavoring of tobacco products; both prior to and on smoking.
• R R and R are hydrogen or lactone, as a tobacco additive; or a spicy apple note may be imparted by the use of beta-methyl-delta valerolactone as a tobacco additive.
• alpha pyrones have been described as being useful in altering the organoleptic characteristics of flavors for foodstuffs as well as fragrances for use in conjunction with perfumed articles.
• Arctander, Perfume and Flavor Chemical (Aroma Chemicals) 1969 contains the following teachings:
• tobacco flavoring compositions and tobacco products having sweet, aromatic, warm, spicy, maple-like,- fruity, coumarin-like, vanillin-like, lactonic, lovage-like, celery-like and/or nut-like flavors and aromas prior to and on smoking may be provided by adding to tobacco flavors and/or to tobaccos themselves one or more alpha pyrones having the generic structure:
• R is hydrogen or methyl and R is C -C alkyl.
• R is hydrogen or methyl and R is C -C alkyl.
• Organoleptic Properties Organoleptic Prior to Properties Compound Smoking On Smoking -n-propyl- Creamy, sweet, Sweet, aromatic, alpha-pyrone coumarin, herbal lactone, coumarin,
• one or more of the alpha-pyrones of our invention, or mixtures thereof is added to tobacco or applied to a smoking article or its component parts in amounts of about l0O-5,000 parts per million (ppm) based on dry weight of the tobacco product.
• the amount of additive is between about 200 and 500 ppm by weight in order to provide a tobacco product having a desired flavor and aroma.
• the amount used will depend upon the amound of flavor and aroma desired and the particular compound or mixture thereof that is used.
• the additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes; Likewise, it will be apparent that only a portion of the tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes or other smoking articles are formed. In such case the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.
• an aged, flue-cured and shredded tobacco is sprayed with a 1 percent ethyl alcohol solution of 6-npentyl-alpha-pyrone in an amount to provide a tobacco containing 200 ppm. by weight of the additive on a dry basis. Thereafter, the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing flavor, an aroma which to some people is described as fruity-coumarin-like and is detectable and pleasing in the main and side smoke streams when the cigarette is smoked.
• the additives falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additive.
• water or volatile organic solvents such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco.
• other flavor-and aroma-producing additives such as (a) Esters, for example:
• While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars or other tobacco products. Furthermore, the compounds may be added to certain tobacco substitutes of natural or synthetic origin.
• the invention has been particularly described with reference to the addition of the compounds directly to tobacco.
• the compound may be applied to the paper of the cigarette or to the wrapper of a cigar. Also, it may be incorporated into the filter tip, the packaging material or the seam paste employed for gluing the cigarette paper.
• a tobacco product is provided which includes the specified additives and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.
• a tobacco formulation (B) is prepared as follows:
• the cigarettes are found to have a spicy, celery-like, fatty, creamy, cereal and nut-like aroma and taste and to be sweeter and spicier than the same formulation without the 4- methyl-fi-n-butyl-alpha-pyrone whether or not the other flavor ingredients of formulation (A) are present therein.
• One-seventh of the cigarettes remains totally without added flavorants.
• One-seventh of the cigarettes contains only formulation (A) added thereto; but no 6- alkyl-alpha-pyrone.
• the cigarettes containing the exemplified 6-alkyl-alpha pyrones are more coumarinlike and/or sweeter, warmer, spicier and more aromatic in nature than those cigarettes not containing these 6- alkyl-alpha pyrones whether or not ingredients of formulation (A) are included in the tobacco.
• 6-alkyl-alphapyrones of our invention can be used in the preparation of a wide variety of tobacco flavors and products.
• EXAMPLE Ill TOBACCO FLAVOR FORMULATION A tobacco flavoring formulation is prepared by admixing the following ingredients:
• Cinnamaldehyde 30.60 Nutmeg Oil, El 0.50 Dibenzyl Ether 3.70
• Eugenol L20 4-methyl-6-n-butylalpha-pyrone 3.00 Vanillin 0.50 3-Phenyl-4-pentenal dimethyl acetal 60.00
• a formulation yielding substantially the same results is produced when one-half of the 4-methyl-6-n-butylalpha-pyrone used is replaced with an equal quantity (1.50 parts by weight) of 4-methyl-6-n-pentyl pyrone.
• the foregoing flavor is added to smoking tobacco at the rates of 0.10, 0.20 and 0.30 percent based on the weight of dry tobacco.
• the tobacco is then manufactured into cigarettes according to standard manufacturing practice.
• the purpose of the 3-phenyl-4-pentenal diethyl acetal is to cause the tobacco, on smoking, to
• R is selected from the group consisting of methyl and hydrogen; and R is C -C alkyl.
• 6- alkyl-alpha-pyrone compound is selected from the group consisting of:
• the tobacco product of claim 1 wherein the concentration of 6-alkyl-alpha-pyrone in the tobacco product is from l00-5000 parts per million, based on the total weight of tobacco on a dry basis.
• the tobacco product of claim 2 wherein the concentration of 6-alkyl-alpha-pyrone in the tobacco product is from 200-500 parts per million based on the total weight of tobacco product on a dry basis.
• 6- alkyl-alpha-pyrone is 6-n-pentyl-alpha-pyrone.
• 6- alkyl-alpha-pyrone is 4-methyl-6-isopropyl-alphapyrone.
• 6- alkyl-alpha-pyrone is 4-methyl-6-n-butyl-alpha-pyrone.
• 6- alkyl-alpha-pyrone is 4-methyl-6-isobutyl-alpha pyrone.

Landscapes

• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Toxicology (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Manufacture Of Tobacco Products (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

Family

ID=23872991

Family Applications (1)

Country Status (6)

Cited By (6)

Citations (1)

• 1974
  • 1974-05-20 US US471785A patent/US3861403A/en not_active Expired - Lifetime
  • 1974-12-06 GB GB5284674A patent/GB1445670A/en not_active Expired
  • 1974-12-11 DE DE2458639A patent/DE2458639C3/de not_active Expired
• 1975
  • 1975-01-10 JP JP50005075A patent/JPS50148600A/ja active Pending
  • 1975-01-10 NL NL7500342A patent/NL7500342A/xx not_active Application Discontinuation
  • 1975-01-14 FR FR7501013A patent/FR2271777A1/fr not_active Withdrawn

Patent Citations (1)

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