US3251366A - Tobacco - Google Patents

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Publication number
US3251366A
US3251366A US453206A US45320665A US3251366A US 3251366 A US3251366 A US 3251366A US 453206 A US453206 A US 453206A US 45320665 A US45320665 A US 45320665A US 3251366 A US3251366 A US 3251366A
Authority
US
United States
Prior art keywords
tobacco
milliliters
grams
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
US453206A
Other languages
English (en)
Inventor
Joseph N Schumacher
Donald L Roberts
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.)
RJ Reynolds Tobacco Co
Original Assignee
RJ Reynolds Tobacco Co
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 RJ Reynolds Tobacco Co filed Critical RJ Reynolds Tobacco Co
Priority to US453206A priority Critical patent/US3251366A/en
Priority to CH74866A priority patent/CH475726A/de
Priority to FR48054A priority patent/FR1482869A/fr
Priority to BE675958D priority patent/BE675958A/xx
Priority to NL6601841A priority patent/NL6601841A/xx
Application granted granted Critical
Publication of US3251366A publication Critical patent/US3251366A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • 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
    • 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
    • C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride

Definitions

  • This invention relates to a tobacco product and has for an object the provision of a composition and process for improving the flavor and aroma of tobacco and tobacco smoke.
  • a further object of this invention is the provision of a process for enhancing or otherwise improving the flavor, aroma and other qualities of certain domestic, oriential, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.
  • An additional object of this invention is to provide a process of preparing a smoking tobacco. or product which when smoked has an enhanced flavor or aroma.
  • a still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.
  • tobacco product is provided to which has been added or which has been treated with a small amount of a compound selected from the group of compounds having the formulae wherein R R R and R are selected from the group consisting of hydrogen and alkyl groups and R is an alkyl group.
  • R R R and R are selected from the group consisting of hydrogen and alkyl groups and R is an alkyl group.
  • the alkyl groups are lower alkyl rad- 3,251,366 Patented May 17, 1966 icals of from 1 to 6 carbon atoms.
  • the compounds falling within the scope of the generic Formulae I and II are a,B-unsaturated-'y-lactones with up to 3 alkyl substituents.
  • R R R R and R can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl and hexyl.
  • R and' R are each methyl, R is pentyl, R is hydrogen and R is normal butyl.
  • three compounds generically indicated in Formulae I, II and III are, respectively, a,/3-dimethyl-'y-pentylidenebutenolide, u, 8-dimethyl-'y-pentylbutenolide, and a,5-dimethyl-y-pentyl- -hydroxybutenolide.
  • Example I In the following will be presented one specific example of a process for preparing a,B-dimethyl-y-pentyl-y-hydroxybutenolide, u,[3-dimethy1 'y pentylidenebutenolide and a,fi-dimethyl-v-p'entylbutenolide which are preferred compounds used as additives for tobacco products in accordance with this invention.
  • the Grignard complex was decomposed by addition of 200 milliliters of a cold aqueous 5 percent sulfuric acid solution. The two layers were separated and the aqueous phase was extracted with 200 milliliters of ether. The ether solutions were combined and extracted with 300 milliliters of aqueous 10 percent sodium carbonate to remove the unreact'ed dimethylmaleic anhydride.
  • the desired lactol (a43-dimethyl-'y-pentyl-y-hydroxybutenolide) remaining in the ether solution was then removed, presumably as the sodium salt, by extraction with 400 milliliters of aqueous 1 M sodium hydroxide solution.
  • the sodium hydroxide solution was acidified, at ()10 C., with 4-N hydrochloric acid and was extracted with 45 0 milliliters of hexane to recover the lactol.
  • 28 grams of lactol, 11 1.4730, boiling point 134 (0.2 mm.) was obtained by evaporation of the hexane and is suitable for use as an additive to tobacco products in accordance with this invention.
  • the lactol was converted to ix,B-dimethyl-y-peneylidenebutenolide by dehydration in the following manner.
  • a mixture of 13 grams of lactol, 6 grams of p-toluenesulfonic acid and 350 milliliters of benezene was refluxed wit-h azeotropic distillation of Water until no more water was evolved. After cooling to room temperature, the reaction mixture was extracted with 200 milliliters of water, milliliters of 10 percent potassium carbonate to completely remove the p-toluenesnlfonic acid and 100 milliliters of water. After drying the benezene solution,
  • This lactone is also suitable for use as an additive to tobacco products is accordance with this invention.
  • the reduction was carried out in a low pressure hydrogenation apparatus at room temperature and an initial hydrogen pressure of 28 pounds per square inch. Hydrogen uptake ceased after one hour.
  • the reaction mixture after removal of the catalyst by filtration, was extracted with 150 milliliters of l M potassium carbonate. The ethyl acetate solution was dried and the solvent was evaporated to yield 3 grams of a,fl-din1ethyl- 'y-pentylbutenolide, 11 1.4657, boiling point 87-89 (0.2 mm.). This represents a 60 percent yield based on the amount of the lactone of a,fi-dimethyl-' -pentylidenebutenolide used.
  • Example lI.3,4-dimetlzyl-A" -butenolide The slow distillation of 16 grams of B-methyllevulinic acid gave a fraction (0.7 gram) which was resolved by vapor-phase chromatography into two peaks. The first and second peaks were identified by infrared and nuclear magnetic resonance data as being 3,4-dimethyl-A' -butenolide and 3,4-dimethyl-A -butenolide.
  • Example V The synthesis of 'y-ethyl-A -butenolide (a) Preparation of 4-ket0hexanoic acid.A mixture of one mole of methyl acrylate 86 grams), three moles of l-nitropropane (267 grams) and 0.5 mole of triethylarnine (50.5 grams) was kept at room temperature for seven days. Distillation of the reaction mixture gave 1 18.5 grams of methyl 4-nitrohexanate, boiling point 97-100 C./2 mm.
  • the various tobacco additives encompassed within the scope of this invention may impart to tobacco an aroma and flavor difficult to characterize.
  • the tobacco additive of Example VI imparts an aroma and flavor which some characterize as a sweet, brown sugar note.
  • a compound embraced by generic Formulae I, II or III or mixtures thereof is added to tobacco or applied to a smoking article or its component parts in amounts of about 0.00005 to 0.5 percent by weight of the product.
  • the amount of additive is between about 0.004 and 0.02 percent by weight in order to provide a tobacco product having a desired flavor and aroma.
  • 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.
  • 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% ethyl alcohol solution of a,/3-dimethyl- 'y-pentylidenebutenolide in an amount to provide a to bacco containing 0.002 percent by weight of the additive on a dry basis.
  • the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques.
  • the cigarette when prepared as indicated has a desired and pleasing flavor, an aroma which to some people is reminiscent of celery seed and is detectable and pleasing in the main and side smoke streams when the cigarette is smoked.
  • a similar product is obtained when tobacco is similarly treated with 0:,[3-dimethyl-y-pentylbutenolide or afi-dimethyl-y-pentyl-'y-hydroxybutenolide.
  • 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 flavorand aroma-producing additives such as those disclosed in United States Patents Nos. 2,766,145, 2,905,575, 2,905,576, 2,978,365 and 3,041,2l1 may be incorporated into the tobacco with the additive of this invention.
  • 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.
  • the compounds may be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.
  • 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 acigar. 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 product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of u,,B-dimethyl-y-pentylidenebutenolide.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of a,,8-dimcthyl-y-pentylbutenolide.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of a,fi-dimethyl-y-pentyl-y-hydroxybutenolide.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of 3,4-dirnethyl-A -butenolide.
  • a tobacco product having added thereto and dispersed therein a small amount sufi'icient to improve the flavor thereof of 3,4,4-trimethyl-A -butenolide.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of 3-isopropyl-N- -butenolide.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of v-ethyl-N -butenolide.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of 2,3-dimethyl-A' -butenolide.
  • a process for improving the flavor of a tobacco product which comprises adding thereto a small amount of a compound selected from the group consisting of compounds having the formulae wherein R R R and R are selected from the group consisting of hydrogen and alkyl groups of l to 6 carbon atoms and R is an alkyl group of not more than 6 carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
US453206A 1965-05-04 1965-05-04 Tobacco Expired - Lifetime US3251366A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US453206A US3251366A (en) 1965-05-04 1965-05-04 Tobacco
CH74866A CH475726A (de) 1965-05-04 1966-01-20 Verfahren zur Verbesserung der Geschmacks- und Aromaeigenschaften eines Tabakprodukts
FR48054A FR1482869A (fr) 1965-05-04 1966-02-01 Procédé et composition pour améliorer l'arôme des tabacs
BE675958D BE675958A (cs) 1965-05-04 1966-02-02
NL6601841A NL6601841A (cs) 1965-05-04 1966-02-14

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US453206A US3251366A (en) 1965-05-04 1965-05-04 Tobacco

Publications (1)

Publication Number Publication Date
US3251366A true US3251366A (en) 1966-05-17

Family

ID=23799600

Family Applications (1)

Application Number Title Priority Date Filing Date
US453206A Expired - Lifetime US3251366A (en) 1965-05-04 1965-05-04 Tobacco

Country Status (4)

Country Link
US (1) US3251366A (cs)
BE (1) BE675958A (cs)
CH (1) CH475726A (cs)
NL (1) NL6601841A (cs)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003013088A (ja) * 2001-06-29 2003-01-15 Soda Aromatic Co Ltd 香気・香味・香喫味付与組成物およびそれを添加した飲食物、香水、化粧品およびたばこ
JP2003013087A (ja) * 2001-06-28 2003-01-15 Soda Aromatic Co Ltd 香気・香味付与組成物およびそれを添加した飲食物、香水、化粧品
WO2007107023A1 (en) * 2006-03-22 2007-09-27 Givaudan Sa Flavorant and fragrance compounds

Citations (2)

* 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
US2872360A (en) * 1957-03-13 1959-02-03 Reynolds Tobacco Co R Tobacco

Patent Citations (2)

* 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
US2872360A (en) * 1957-03-13 1959-02-03 Reynolds Tobacco Co R Tobacco

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003013087A (ja) * 2001-06-28 2003-01-15 Soda Aromatic Co Ltd 香気・香味付与組成物およびそれを添加した飲食物、香水、化粧品
JP2003013088A (ja) * 2001-06-29 2003-01-15 Soda Aromatic Co Ltd 香気・香味・香喫味付与組成物およびそれを添加した飲食物、香水、化粧品およびたばこ
WO2007107023A1 (en) * 2006-03-22 2007-09-27 Givaudan Sa Flavorant and fragrance compounds
US20100291275A1 (en) * 2006-03-22 2010-11-18 Stefan Michael Furrer Flavorant and Fragrance Furan-2(5H)-One Compounds

Also Published As

Publication number Publication date
BE675958A (cs) 1966-08-02
NL6601841A (cs) 1966-11-07
CH475726A (de) 1969-07-31

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