US3563248A - Tobacco product - Google Patents

Tobacco product Download PDF

Info

Publication number
US3563248A
US3563248A US825421A US3563248DA US3563248A US 3563248 A US3563248 A US 3563248A US 825421 A US825421 A US 825421A US 3563248D A US3563248D A US 3563248DA US 3563248 A US3563248 A US 3563248A
Authority
US
United States
Prior art keywords
tobacco
lactone
tobacco product
flavor
product
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
Application number
US825421A
Inventor
Tilford F Riehl Jr
John E Kennedy Jr
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Brown and Williamson Holdings Inc
Original Assignee
Brown and Williamson Tobacco Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Brown and Williamson Tobacco Corp filed Critical Brown and Williamson Tobacco Corp
Application granted granted Critical
Publication of US3563248A publication Critical patent/US3563248A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • A24B15/36—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)

Abstract

A tobacco product is described which includes a 3-(2hydroxycyclohexyl) propionic acid, delta lactone having the structure

D R A W I N G

Description

United States Patent [72] Inventors [21 Appl. No. [22] Filed [45] Patented [73] Assignee [54] TOBACCO PRODUCT 3 Claims, No Drawings 52 us. c1 '131/17, 131/144, 131/15, 131/9 [51] Int. Cl A24b 15/04 [50] Field ofSearch 131/17,
[56] References Cited UNITED STATES PATENTS 2,766,147 10/1956 Rowland 1 1/17 3,217,716 11/1965 Robertsetal 3,342,186 9/1967 Cook .1
OTHER REFERENCES SHMUK, A.A. THE CHEMISTRY AND TECHNOLOGY OF TOBACCO, PISHCHEPROMIZDAT, MOSCOW (1953) VOL. III, p.551.
Primary Examiner-Samuel Koren Assistant Examiner- Dennis J. Donohue Attorney-Kane, Dalsimer, Kane, Sullivan and Kurucz ABSTRACT: 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.
BACKGROUND OF THE INVENTION Many substances are known which when added to a tobacco product improve the flavor and aroma of the tobacco smoke. Many of these substances, as for example, menthol, are highly volatile and impart to the tobacco smoke a flavor and aroma generally characteristic of the substance added. Much time and effort are devoted by the tobacco industry to develop additives which, when applied to a tobacco product, enhance the natural flavor of the tobacco as well as improve the organoleptic qualities of the tobacco smoke.
BRIEF SUMMARY A tobacco flavorant has now been discovered which, when added to smoking tobacco, substantially enhances the natural flavor and aroma of the tobacco and improves 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.
DESCRIPTION OF THE INVENTION In accordance with this invention, 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:
EXAMPLE 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
ethereal extract is then washed with an aqueous solution of sodium bicarbonate, dried and concentrated. Distillation separates 68 percent of the product which is identified as 3-(2- hydroxycyclohexyl) propionic acid, delta lactone. This lactone consists of approximately 60 percent of the trans isomer and 40 percent of the cis isomer.
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. After the ethyl alcohol is evaporated from the treated 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. After the ethyl alcohol is evaporated from the tobacco, cigarettes are made having a standard cellulose acetate filter. These cigarettes are used as the control for testing purposes. When compared to the control cigarettes, 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.
It should be understood that the term 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.
We claim:
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.
2. A tobacco product in accordance with claim 1 wherein the lactone is present in amounts of about 0.0001 to 2.0 percent by weight of the tobacco.
3. A tobacco product in accordance with claim 2 wherein the lactone is present in amounts of about 0.0001 to 0.05 percent by weight of the tobacco.

Claims (2)

  1. 2. A tobacco product in accordance with claim 1 wherein the lactone is present in amounts of about 0.0001 to 2.0 percent by weight of the tobacco.
  2. 3. A tobacco product in accordance with claim 2 wherein the lactone is present in amounts of about 0.0001 to 0.05 percent by weight of the tobacco.
US825421A 1969-05-16 1969-05-16 Tobacco product Expired - Lifetime US3563248A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US82542169A 1969-05-16 1969-05-16

Publications (1)

Publication Number Publication Date
US3563248A true US3563248A (en) 1971-02-16

Family

ID=25243976

Family Applications (1)

Application Number Title Priority Date Filing Date
US825421A Expired - Lifetime US3563248A (en) 1969-05-16 1969-05-16 Tobacco product

Country Status (3)

Country Link
US (1) US3563248A (en)
DE (1) DE2023914A1 (en)
GB (1) GB1242368A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3996941A (en) * 1975-05-08 1976-12-14 R. J. Reynolds Tobacco Company Tobacco product
US6557561B1 (en) * 1997-10-24 2003-05-06 Japan Tobacco Inc. Cigarette paper having a flavorant which improves sidestream smoke smell, and a cigarette

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766147A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US3217716A (en) * 1963-11-14 1965-11-16 Reynolds Tobacco Co R Tobacco composition
US3342186A (en) * 1964-08-07 1967-09-19 Allied Chem Aromatized tobaccos

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766147A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US3217716A (en) * 1963-11-14 1965-11-16 Reynolds Tobacco Co R Tobacco composition
US3342186A (en) * 1964-08-07 1967-09-19 Allied Chem Aromatized tobaccos

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SHMUK, A.A, THE CHEMISTRY AND TECHNOLOGY OF TOBACCO, PISHCHEPROMIZDAT, MOSCOW VOL. III *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3996941A (en) * 1975-05-08 1976-12-14 R. J. Reynolds Tobacco Company Tobacco product
US6557561B1 (en) * 1997-10-24 2003-05-06 Japan Tobacco Inc. Cigarette paper having a flavorant which improves sidestream smoke smell, and a cigarette

Also Published As

Publication number Publication date
DE2023914A1 (en) 1970-11-19
GB1242368A (en) 1971-08-11

Similar Documents

Publication Publication Date Title
US3476118A (en) Method of influencing tobacco smoke aroma
US2766148A (en) Tobacco
US2886042A (en) Cigarette paper
RU2048780C1 (en) Smoking composition and a method of its producing
DE3067665D1 (en) Flavourant composition for tobacco, method for its production and tobacco product containing said composition
US3818915A (en) Tobacco substitute smoking material
US2766146A (en) Tobacco
US4036237A (en) Smoking composition
US3563248A (en) Tobacco product
US2460285A (en) Tobacco products and method of making them
US5137036A (en) Smoking compositions containing a vanillin-release additive
US3381691A (en) Tobacco product
US3217718A (en) Tobacco
NO127732B (en)
US3890981A (en) Novel process for altering the organoleptic properties of tobacco using one or more alpha-pyrones and process
US3559656A (en) Tobacco product
US4014348A (en) Smoking mixture
GB1582459A (en) Dihydropyrans
EP0514202A2 (en) Smoking compositions containing a vanillin-release additive
US4690157A (en) Smoking compositions containing a flavorant-release additive
US3334637A (en) Smoking product having flavorant additive
US2886041A (en) Cigarette paper
US3545452A (en) Tobacco product including releasable flavorant
US3545450A (en) Tobacco product including releasable flavorant
US3372701A (en) Tobacco