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

• a tobacco product is described which includes a 3-(2-hydroxycyc1ohexyl) propionic acid, delta lactone having the structure Small amounts of this lactone enhance the flavor and aroma of the tobacco and improve the organoleptic qualities of the tobacco smoke.
• An object of this invention therefore is to provide a flavorant for tobacco which will improve the tobaccos flavor and aroma, and the tobacco smoke s organo leptic qualities.
• tobacco flavor is enhanced by the addition of a saturated lactone 3-(2-hydroxycyclohexyl) propionic acid, delta lactone having the chemical structure tion, the following example is given:
• a keto ester having the chemical structure is formed by reaction of cyclohexanone with methyl acrylate in a Michael condensation.
• a keto acid having the structure 0 ll -CH2CH2C 02H is formed from the aforesaid keto ester by saponification.
• a solution of 0.11 mole of the keto acid, 0.115 mole of sodium hydroxide and 0.05 mole of sodium borohydride in milliliters of methanol is stirred under a nitrogen atmosphere for 4 hoursat 0 C. This solution is then acidified, saturated with ammonium sulfate and thereafter extracted with ether.
• the resulting 3-(2-hydroxycyclohexyl) propionic acid, delta lactone is dissolved in ethyl alcohol and sprayed on shredded and blended domestic tobacco in amounts of 0.005 percent of the lactone by weight of the tobacco.
• cigarettes are made having a standard cellulose acetate filter.
• a second quantity of shredded and blended tobacco is sprayed with the same relative quantity of ethyl alcohol.
• cigarettes are made having a standard cellulose acetate filter. These cigarettes are used as the control for testing purposes.
• the 3-(2-hydroxycyclohexyl) propionic acid, delta lactone-treated cigarettes show a distinct improvement in the tobaccos flavor and aroma and the tobacco smoke s organoleptic properties.
• Procedures for making the above noted lactone contemplated by this invention are described in Vol. 62, pages 283287 of the Journal of the American Chemical Society, and Vol. 27, pages 4141 to 4146 of the Journal of Organic Chemistry.
• tobacco product as used herein are products made from tobacco such, for example, as cigarettes (either filtered or unfiltered), pipe tobacco and cigars.
• the lactone flavor additive may also be added to reconstituted tobacco or tobacco substitutes. It is also evident that the lactone contemplated by this invention may be added not only to the tobacco or filter tip section of a tobacco product but also to the cigarette paper wrapper or seam paste employed on the cigarette paper, or to the packaging material for the tobacco product. It is advantageous, however, that the lactone additive be included in the blended and shredded tobacco prior to its formation into a tobacco product.
• lIA tobacco product having added thereto a small amount of a lactone having the chemical structure such amount being sufficient to enhance the flavor or aroma of the tobacco product.

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)

Applications Claiming Priority (1)

Publications (1)

Family

ID=25243976

Family Applications (1)

Country Status (3)

Cited By (2)

Citations (3)

• 1969
  • 1969-05-16 US US825421A patent/US3563248A/en not_active Expired - Lifetime
• 1970
  • 1970-05-15 DE DE19702023914 patent/DE2023914A1/de active Pending
  • 1970-05-15 GB GB23777/70A patent/GB1242368A/en not_active Expired

Patent Citations (3)

Non-Patent Citations (1)

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