Method of providing flavorful and aromatic compounds

Details Method of providing flavorful and aromatic compounds Method of providing flavorful and aromatic compounds

2001-07-19

2002-08-06

Derrington, James (Department: 1731)

Tobacco

Product or device having identifiable constituent to flavor...

Organic compound

C131S274000, C131S277000, C131S278000, C428S905000, C206S242000

Reexamination Certificate

active

06428624

ABSTRACT:

FIELD OF INVENTION
The present invention relates to smoking articles such as cigarettes, and in particular to process for providing a flavorful and aromatic composition similar to those characteristics of certain tobaccos.
BACKGROUND OF THE INVENTION
Popular smoking articles, such as cigarettes, have a substantially rod shaped structure and include a charge of smokable material such as strands or shreds of tobacco (e.g., cut filler) surrounded by a paper wrapper thereby providing a so-called “tobacco rod.” Numerous popular cigarettes have cylindrical filter elements aligned in an end-to-end relationship with the tobacco rod. Typically, filter elements are constructed from fibrous materials such as cellulose acetate, have a circumscribing plug wrap, and are attached to the tobacco rod using tipping material.
Many types of smoking products and improved smoking articles have been proposed through the years as improvements upon, or as alternatives to, the popular smoking articles. Recently, U.S. Pat. No. 4,708,151 to Shelar; U.S. Pat. No. 4,714,082 to Banerjee et al.; U.S. Pat. No. 4,756,318 to Clearman et al.; and U.S. Pat. No. 4,793,365 to Sensabaugh, Jr. et al.; and European Patent Publication Nos. 212,234 and 277,519 propose cigarettes and pipes which comprise a fuel element, an aerosol generating means physically separate from the fuel element, and a separate mouth-end piece. Such types of smoking articles provide natural tobacco flavors to the smoker thereof by heating, rather than burning, tobacco in various forms.
Flavor and aroma are important characteristics of smoking articles. To improve the flavor and aroma in smoking articles, flavorful and aromatic substances, including various natural extracts, have been included in smoking articles. For example, various processes for producing and using tobacco extracts, aroma oils and concentrates are proposed in the U.S. Pat. No. 3,136,321 to Davis; U.S. Pat. No. 3,316,919 to Green; U.S. Pat. No. 3,424,171 to Rooker; U.S. Pat. No. 4,421,126 to Gellatly and U.S. Pat. No. 4,506,682 to Mueller and European Patent Publication No. 338,831 to Clapp et al.
U.S. Pat. No. 5,413,122 to Shu issued on May 9, 1995 discloses making a flavorful and aromatic composition from &bgr;-hydroxy &agr;-amino acids by contacting the amino acids with a liquid having an aqueous character followed by heat treatment in an enclosed environment to provide an aqueous solution of volatile pyrazine flavorants. The ratio of liquid to amino acid is 4:1 to 40:1. The resulting aqueous extract containing flavorful pyrazines is then applied to smoking materials to provide flavor and aroma in the smoking articles.
It has also been proposed to react sugars with amino acids to produce desirable flavorants for smoking articles and foods. For example, U.S. Pat. No. 3,478,015 discloses heating an amino acid and a sugar in the presence of a polyhydric alcohol and using the reaction product as a flavoring material.
U.S. Pat. No. 3,920,026 describes reacting the amino acid valine with a sugar, other hydroxycarbonyl compound, or dicarbonyl compound under heat treatment in a solvent such as glycerol or propylene glycol and at a temperature of about 100° C. to about 200° C. for about 0.5 to 5 hours. Optionally, a catalyst such as a flavanoid or hydroxyacid is included in the reaction. The reaction products can be used as flavorants in tobacco compositions.
U.S. Pat. No. 4,306,577 discloses the production of flavorants for smoking compositions by reacting reducing sugars and selected amino acids in the presence of ammonium hydroxide and optionally in the presence of an aldehyde in an essentially solvent-free system at a temperature range of 90° C. to 115° C. The selected amino acids are those that have at least two nitrogens such as glutamine, asparagine, lysine, and arginine.
Similarly, U.S. Pat. No. Re. 32,095 discloses reacting a reducing sugar with a source of ammonia in the presence of a trace amount of certain amino acids at a temperature in the range of about 90° C. to about 115° C. for about 5 to 15 minutes. The trace amino acids include aspartic acid, glutamic acid, asparagine, and glutamine. The weight ratio of sugar to amino acid is in the range of 200-300:1, and the weight ratio of sugar to ammonia source is about 5-15:1.
Because of the volatile nature of flavorant and aroma materials, they are often lost during use in cigarette manufacturing steps. Also quantities of the flavorant and aroma materials can diminish during the storage of the finished smoking articles and it is often necessary to increase the initial content of flavorants to compensate.
SUMMARY OF THE INVENTION
In accordance with the present invention, highly desirable flavorful and aromatic substances, and particularly flavorful and aromatic substances similar to and complementing those found in smokable materials are generated by heating a mixture comprising a reducing sugar source, a base catalyst, and an amino acid source material having a selectively enriched content of at least one amino acid selected from the group consisting of serine, threonine, valine, leucine, and isolecine. The resulting composition of flavorful and aromatic substances from the reaction includes a substantial quantity of flavorful and aromatic pyrazines that have low volatility and a low sensory threshold, i.e., powerful sensory attributes at very low concentrations. Examples of such pyrazines include, but are not limited to, methylcyclopentapyrazine, cyclopentapyrazine, 2-methyl-5,6,7,8-tetrahydroquinoxaline, dimethyl-isopropenyl pyrazine, dimethyl-propenyl pyrazine, methyl-propenyl pyrazine, acetylpyrazine, 2,3,5-trimethyl-6-ethylpyrazine, 2-methyl-3,5-dimethyl pyrazine, 2,6-diethyl pyrazine, trimethyl pyrazine, dimethyl pyrazine, etc. These pyrazines are characterized by larger side chains than flavorant pyrazines normally added to tobacco and/or generated in substantial quantities during smoking. The larger side chains have dual effects of decreasing the volatility of the flavorant while at the same time increasing the flavor potency of the flavorant substances typically by many orders of magnitude. Thus, less quantities of the flavorant and aroma materials can be used in smoking articles to provide a significantly greater enhancement of flavor and aroma. At the same time, loss of the flavorants during manufacturing and storage of the smoking articles is minimal.
Accordingly, in a first aspect, the present invention relates to a method for providing flavorful and aromatic substances for use in a smoking article. A mixture is provided comprising a reducing sugar source, a base catalyst, and an amino acid source having a selectively enriched content of at least one amino acid selected from the group consisting of serine, threonine, valine, leucine, and isoleucine. The mixture is then subjected to heat treatment for a time and under conditions sufficient to provide flavorful and aromatic substances.
The amino acid source can be a natural material containing endogenous free amino acids, or a composition comprising extracted or synthetic amino acids. The selective enrichment is the result of the incorporation of one or more exogenous free amino acids selected from the group consisting of serine, threonine, valine, leucine, and isoleucine in the amino acid source. Preferably, the mixture contains from about 0.1 to about 20%, more preferably from about 0.5% to about 10%, and most preferably from about 3% to about 5% by weight, e.g., 4% by weight, cumulatively, of amino acids selected from the group consisting of serine, threonine, valine, leucine, and isoleucine based on the total weight of the mixture.
Preferably, the mixture comprises materials normally used in casing, such as licorice and cocoa that contain endogenous free amino acids. More preferably, the mixture is formed by adding at least one desirable amino acid and at least one base catalyst to a conventional casing.
The mixture of reducing sugar source material, base catalyst and the amino acid source having a selectively enriched content of serine, threonine, leucine,

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