CH549955A - Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs - Google Patents

Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs

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Publication number
CH549955A
CH549955A CH915671A CH915671A CH549955A CH 549955 A CH549955 A CH 549955A CH 915671 A CH915671 A CH 915671A CH 915671 A CH915671 A CH 915671A CH 549955 A CH549955 A CH 549955A
Authority
CH
Switzerland
Prior art keywords
tobacco
dione
trimethyl
diene
ccl4
Prior art date
Application number
CH915671A
Other languages
French (fr)
Original Assignee
Firmenich & Cie
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 Firmenich & Cie filed Critical Firmenich & Cie
Priority to CH34173A priority Critical patent/CH542591A/en
Priority to CH915671A priority patent/CH549955A/en
Priority to DE2202066A priority patent/DE2202066C2/en
Priority to DE19722202065 priority patent/DE2202065A1/en
Priority to CA132,661A priority patent/CA991941A/en
Priority to FR7201578A priority patent/FR2175236A5/fr
Priority to GB889273A priority patent/GB1380196A/en
Priority to GB259172A priority patent/GB1380191A/en
Priority to GB5474373A priority patent/GB1380193A/en
Priority to GB2389073A priority patent/GB1380202A/en
Priority to GB889573A priority patent/GB1380199A/en
Priority to GB5474573A priority patent/GB1380195A/en
Priority to NLAANVRAGE7200728,A priority patent/NL170491C/en
Priority to GB4591873A priority patent/GB1380209A/en
Priority to GB889673A priority patent/GB1380200A/en
Priority to GB2389373A priority patent/GB1380205A/en
Priority to GB889373A priority patent/GB1380197A/en
Priority to JP47007544A priority patent/JPS519038B1/ja
Priority to GB5474473A priority patent/GB1380194A/en
Priority to GB2388973A priority patent/GB1380201A/en
Priority to GB889473A priority patent/GB1380198A/en
Priority to GB2389273A priority patent/GB1380204A/en
Priority to GB2389173A priority patent/GB1380203A/en
Priority to GB889173A priority patent/GB1380192A/en
Priority to FR7309593A priority patent/FR2168121B1/fr
Publication of CH549955A publication Critical patent/CH549955A/en
Priority to US482776A priority patent/US3920027A/en
Priority to US05/482,512 priority patent/US3989857A/en
Priority to CA226,238A priority patent/CA1011758A/en
Priority to US05/586,368 priority patent/US4092989A/en
Priority to US05/586,310 priority patent/US4029106A/en
Priority to US05/586,383 priority patent/US4029108A/en
Priority to US05/586,387 priority patent/US3981311A/en
Priority to US05/586,386 priority patent/US4014350A/en
Priority to US05/586,384 priority patent/US4031902A/en
Priority to US05/586,380 priority patent/US3983885A/en
Priority to US05/586,382 priority patent/US4029107A/en
Priority to US05/586,385 priority patent/US3937228A/en
Priority to JP12121575A priority patent/JPS5313719B2/ja
Priority to JP12121875A priority patent/JPS535759B2/ja
Priority to JP50121219A priority patent/JPS5179766A/en
Priority to JP12121675A priority patent/JPS5310160B2/ja
Priority to CA244,928A priority patent/CA1004601A/en
Priority to NLAANVRAGE8104372,A priority patent/NL173706C/en
Priority to NL8104371A priority patent/NL8104371A/en
Priority to NLAANVRAGE8104373,A priority patent/NL174219C/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2028—Carboxy compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • 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
    • A24B15/365—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having nitrogen and sulfur as hetero atoms in the same ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)
  • Epoxy Compounds (AREA)

Abstract

The organoleptic props. of tobacco and other prods. are improved or modified by adding (i) a cpd. of formula (I): R-C(O)NHR1 (where R and R1 are 1-6 alkyl or H); (ii) cycloaliphatic esters and ketones; (iii) phenol derivs.; (iv) heterocyclic ketones of formula (II): with a double bond in the posn. of 1 of the dotted lines, where X is H or OH if the double bond is in the ring, or O if the double bond is outside the ring; R2 and R3 are lower alkyl and Z is O or S; (v) caryophyllene derivs. or (vi) epoxy-beta-ionone, 6-methyl-hepta-3,5-diene-2-one, 3-isopropylcyclopent-2-ene-1-one, octa-3,5-diene-2-one, nonane-2,5,8-trione, 2-methyl-5-(alpha-methyl-alpha-hydroxyethyl)cyclohex-2-ene-1-one, or 4-methylthiobutan-2-one. Food, fodder, drinks and pharmaceuticals may be treated, as well as tobacco. The taste of tea, coffee and lime-flower tea can be modified; the additives may be used in meat, esp. smoked meat, and cocoa.

Description

  

  
 



   La présente invention a pour objet une composition aromatisante, pour renforcer, améliorer ou modifier les propriétés organoleptiques du tabac.



   Il est bien connu que le tabac utilisé pour la fabrication des cigarettes est essentiellement composé d'un mélange de différents types de tabacs qui donnent ainsi à la fumée l'arôme particulier que   l'on    désire obtenir. Ainsi, les cigarettes ordinaires contiennent des mélanges de tabacs de Virginie, Maryland ou du Kentucky et de tabacs orientaux ou turcs, les proportions respectives variant selon l'arôme particulier recherché. Il est également courant d'utiliser des substances aromatisantes et des humectants, afin d'améliorer l'arôme desdits mélanges de tabac.



   Un des objets de la présente invention consiste en une composition destinée à renforcer, améliorer ou modifier les propriétés organoleptiques de la fumée de tabac (tabac naturel ou produit de remplacement du tabac, d'origine naturelle ou synthétique), ladite composition aromatisante étant caractérisée en ce qu'elle contient au moins un des composés appartenant au groupe des dérivés alicyliques suivants: a)   3,5,5-triméthyl-2,3-époxycyclohexa-1,4-dione    c.n.



  b)   4,4,Striméthylcyclohexa-2,5-diène-2-ol-1-one    c.n.



  c)   3,5,5-triméthylcyclohex-2-ène-2-ol-1-one    J. Org. Chem.



   24, 719 (1959)
 A la suite de la désignation de chaque produit figure la référence de littérature mentionnant une méthode pour leur préparation.



  Dans les cas de nouveaux composés, les méthodes de   synthése    sont mentionnées au sein de la description qui suit. De tels composés sont désignés par l'abréviation  c.n. .



   Les résultats des tests d'évaluation organoleptique sont donnés dans les exemples spécifiques.



   Un autre objet de la présente invention concerne l'utilisation des compositions aromatisantes définies plus haut comme agents modificateurs du goût et de l'arôme de la fumée de tabac.



   Les compositions aromatisantes objets de la présente invention peuvent être employées sous diverses formes. La nature, la solubilité et la stabilité de leurs constituants détermineront la forme sous laquelle la composition doit être utilisée. Il est cependant préférable d'utiliser lesdites compositions sous forme de solutions. Une méthode appropriée pour l'aromatisation du tabac consiste en l'aspersion du tabac à l'aide d'une solution alcoolique du produit ou de la composition aromatisante. On peut également utiliser comme solvant des mélanges d'alcool et de propylèneglycol.



   Les proportions pour l'emploi des composés alicycliques men   tionnés    dans des compositions aromatisantes. ou l'utilisation desdites compositions selon l'invention, peuvent varier dans de larges limites. Ces proportions varient selon l'effet organoleptique recherché et selon la provenance du tabac auquel les compositions aromatisantes susmentionnées sont ajoutées. Par exemple, des effets aromatisants intéressants peuvent être obtenus avec des quantités de l'ordre de I à 1000 ppm, quantités basées sur le poids des composés alicycliques mentionnés dans les produits aromatisés terminés. Des effets plus particuliers cependant peuvent être obtenus avec des proportions de 5 et même 10%. On utilise de préférence des quantités comprises entre 10 et 200 ppm. Dans tous les cas, les limites données ci-dessus peuvent bien entendu varier selon l'effet aromatisant recherché.



   La présente invention sera mieux illustrée par l'exemple suivant.



  Exemple:
 7 g d'une solution à 1% de   3.5,5-triméthyl-2,3-époxycyclohexa-      1 ,4-dione    dans l'alcool éthylique à 95% ont été dispersés sur 100 g d'un mélange de tabacs du type  american blend . Le tabac ainsi aromatisé a ensuite été utilisé pour la manufacture de cigarettes  test  dont la fumée a été soumise à une évaluation organoleptique, après comparaison de celle-ci avec la fumée de cigarettes  témoin , non aromatisées, dont le tabac avait été préalablement traité par de l'alcool éthylique à 95%.



   Le groupe d'experts requis a été unanime à déclarer que la fumée des cigarettes  test  possédait un caractère plus doux et présentait une note herbeuse rappelant le goût de la fumée de cigare.



   D'autres échantillons ont été également évalués selon le procédé de l'exemple ci-dessus. Le tableau suivant donne la liste des produits ainsi évalués et mentionne les quantités utilisées pour l'aromatisation recherchée, ainsi que l'arôme développé.



   Tableau
Composé Quantité   [g]l    Evaluation organoleptique2 a)   1,010,0    doux, phénolique, caractère  flue-cured , noix, chocolat b) 7,0 doux, boisé, note anisée, plus plaisant c) 1,010,0 doux, herbeux   
 Les quantités indiquées se référent à des quantités de solutions alcooliques à 1% (alcool éthylique 95%).



  2 Les caractéres mentionnés se réfèrent aux propriétés organoleptiques des composés testés sur des    tabacs et comparés avec des tabacs non aromatisés.



   La   4,4,6-triméthylcyclohexa-2,5-diène-2-ol-1-one,    composé alicyclique nouveau, peut être préparé ainsi:
 a)   Un mélange équimoléculaire d'isophorone (13,82 g; 0,1    mole) et de N-bromo-succinimide (17,80 g; 0,1 mole) en présence d'une trace de   a, '-azodiisobutyronitrile    a été porté à reflux dans 500   ml    de   CCl4    pendant 15 mn. Après refroidissement, on a ajouté au mélange de réaction environ 500   ml    d'éther de pétrole   (30-50"C)    et filtré le succinimide précipité. Par évaporation des parties volatiles on a obtenu la   3,5,5-triméthyl4-bromo-cyclohex-2éne-one    brute.



   RMN   (CCl4):    1,16 (3H,s); 1,25 (3H,s); 2,11 (3H,s); 2,07 (1H,d,
J=   16cops);    2,53   (1H,d,    J= 16 cps); 4,45   (1H,s);    5,78 (lH,s) 6 ppm.



   b) 43,4 g de   3,5,5-tnméthyl4-bromo-cyclohex-2-ène-one    ont été ajoutés en 30 mn à une solution maintenue à   40"C    de triméthylamine-N-oxyde anhydre (32 g) dans 100   ml    de chloroforme anhydre.



  La réaction était légèrement exothermique et la température du mélange a été maintenue à environ   45 50c C    pendant toute l'addition. Après avoir été maintenu à reflux pendant 20 mn, le mélange de réaction a été refroidi et versé sur 110   ml    d'H2SO4 dilué à 10%.

 

  La phase organique a été ensuite séparée, lavée à l'eau (3   x),    au carbonate de sodium 10% (3 x ) et de nouveau à   l'eau    (3   x).   



   L'évaporation des parties volatiles a fourni un résidu qui, par distillation, a donné un produit à éb.   47-60     C/0,001 Torr. Ce produit a été repris avec de l'éther de pétrole   (30-50 C),    lavé avec une solution aqueuse à 5% de carbonate de soude (2 x) puis à la soude caustique à 2% dans l'eau (5 x ). Les lavages à la soude caustique ont été acidifiés et   réextraits    immédiatement à l'éther sulfurique.



   Après lavage, séchage sur MgSO4 et évaporation des parties volatiles, les extraits éthérés ont fourni 8 g de produit cristallisé ayant  une pureté de 95%, suivant l'analyse effectuée par chromatographie en phase gazeuse.



   La purification suivante, effectuée par sublimation à   70-80"    C/10
Torr, a donné 6 g de   4,4,6-triméthyl-cyclohexa-2,5-diène-2-ol-1    -one.



  Le produit a donné un test positif par traitement avec une solution de chlorure ferrique (coloration bleu violette). F.   46"C.   



     IR (CCl4):    1630, 1650,   3440 cm-l   
 UV:   ta XH=205,    249, 310 me   =5650,    7880, 2420 respective
 ment)
 SM:   M+=152,m/e:    109
 RMN   (CCl4):    1,27 (6H,s); 1,92 (3H,s); 5,97 (1H, pseudo d, J= environ 2,5 cps); 6,34   (1H,m);    6,65   (IH,m);      8    ppm.



   Dans les conditions d'analyse utilisées, la structure de ce composé a été définie suivant la formule
EMI2.1     

 Cependant, il faut s'attendre à ce que, dans d'autres conditions, un équilibre céto-énolique s'établisse comme suit:
EMI2.2     

 céto-enol dicétone
 Si, à la place de   l'oxyde    de triméthylamine, on utilise d'autres oxydes d'une amine aliphatique ou cycloaliphatique tertiaire, des résultats analogues sont obtenus. De même, comme agent halo   génant,    on peut utiliser, à part le N-bromo-succinimide mentionné, des agents halogénants capables de fournir un halogène positif.



   La   3,5,5-triméthyl-2,3-époxy-cyclohexa-1,4-dione    peut être préparée comme indiqué ci-dessous:
 2 ml d'une solution aqueuse de NaOH 6N ont été ajoutés durant 15 mn, à   15"C,    à un mélange de 3,7 g de 3,5,5-triméthyl   cyclohex-2-ène-1,4-dione    et 8,3 ml d'une solution de péroxyde d'hydrogène à 30% dans 27 ml de méthanol. Le mélange réactionnel a ensuite été agité durant 3 heures à   20-25"C,    puis traité avec de l'eau et extrait à   l'éther.    Les extraits organiques réunis ont été lavés à l'eau jusqu'à neutralité, séchés sur MgSO4 et évaporés, à sec. On obtient ainsi 3,33 g (82%) du produit désiré, éb.



     40"C/0,001    Torr.



   IR: 1715cm-1; SM: M+=168; m/e: 56
 RMN   (CCl4):    1,05 (3H,s); 1,25 (3H,s); 1,50 (3H,s); 2,08 (1H,d,
J= 13 cps); 3,09   (1H,d,      J= 13    cps); 3,47   (1H,s)      8    ppm.



   La   3,5,5-triméthylcyclohex-2-ène-1,4-dione,    utilisée comme produit de départ dans la préparation ci-dessus, peut être obtenue selon le procédé décrit dans Tetrahedron, Suppl. 8/I, p.   1(1966).   

 

      REVENDICATION I   
 Composition destinée à renforcer, améliorer ou modifier les propriétés organoleptiques de la fumée de tabac, caractérisée en ce qu'elle contient au moins un des composés appartenant au groupe des dérivés alicycliques suivants: a)   3,5,5-triméthyl-2,3-époxycyclohexa-1,4-dione,    b)   4,4,6-triméthylcyclohexa-2,5-diène-2-oî-1 -one,    c)   3,5,5-triméthyîcyclohex-2-ène-2-ol-1 -one.   



   REVENDICATION   II   
 Utilisation d'une composition telle que définie à la revendication I, comme agent modificateur du goût et de l'arôme de la fumée de tabac.

**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.



   



  
 



   The present invention relates to a flavoring composition for strengthening, improving or modifying the organoleptic properties of tobacco.



   It is well known that the tobacco used for the manufacture of cigarettes is essentially composed of a mixture of different types of tobacco which thus give the smoke the particular flavor which is desired. Thus, ordinary cigarettes contain mixtures of tobacco from Virginia, Maryland or Kentucky and oriental or Turkish tobacco, the respective proportions varying according to the particular flavor desired. It is also common to use flavoring substances and humectants, in order to improve the aroma of said tobacco mixtures.



   One of the objects of the present invention consists of a composition intended to strengthen, improve or modify the organoleptic properties of tobacco smoke (natural tobacco or tobacco replacement product, of natural or synthetic origin), said flavoring composition being characterized by that it contains at least one of the compounds belonging to the group of the following alkyl derivatives: a) 3,5,5-trimethyl-2,3-epoxycyclohexa-1,4-dione cn



  b) 4,4, Strimethylcyclohexa-2,5-diene-2-ol-1-one c.n.



  c) 3,5,5-trimethylcyclohex-2-en-2-ol-1-one J. Org. Chem.



   24, 719 (1959)
 Following the designation of each product appears the literature reference mentioning a method for their preparation.



  In the case of new compounds, the synthesis methods are mentioned in the description which follows. Such compounds are designated by the abbreviation c.n. .



   The results of the organoleptic evaluation tests are given in the specific examples.



   Another object of the present invention relates to the use of the flavoring compositions defined above as agents for modifying the taste and aroma of tobacco smoke.



   The flavoring compositions which are the subjects of the present invention can be used in various forms. The nature, solubility and stability of their constituents will determine the form in which the composition is to be used. It is, however, preferable to use said compositions in the form of solutions. A suitable method of flavoring tobacco is by sprinkling the tobacco with an alcoholic solution of the flavoring product or composition. Mixtures of alcohol and propylene glycol can also be used as solvent.



   The proportions for the use of the alicyclic compounds mentioned in flavoring compositions. or the use of said compositions according to the invention, can vary within wide limits. These proportions vary according to the desired organoleptic effect and according to the origin of the tobacco to which the above-mentioned flavoring compositions are added. For example, interesting flavoring effects can be obtained with amounts of the order of 1 to 1000 ppm, amounts based on the weight of the alicyclic compounds mentioned in the finished flavored products. More particular effects, however, can be obtained with proportions of 5 and even 10%. Amounts of between 10 and 200 ppm are preferably used. In all cases, the limits given above can of course vary according to the flavoring effect sought.



   The present invention will be better illustrated by the following example.



  Example:
 7 g of a 1% solution of 3.5,5-trimethyl-2,3-epoxycyclohexa- 1, 4-dione in 95% ethyl alcohol were dispersed over 100 g of a mixture of tobacco of the American type blend. The tobacco thus flavored was then used for the manufacture of test cigarettes, the smoke of which was subjected to an organoleptic evaluation, after comparison of the latter with the smoke of control cigarettes, unflavored, the tobacco of which had been previously treated with 95% ethyl alcohol.



   The requested expert group unanimously declared that the smoke of the test cigarettes had a milder character and had a grassy note reminiscent of the taste of cigar smoke.



   Other samples were also evaluated according to the method of the example above. The following table gives the list of products thus evaluated and mentions the quantities used for the desired flavoring, as well as the developed flavor.



   Board
Compound Quantity [g] l Organoleptic evaluation2 a) 1.010.0 sweet, phenolic, flue-cured character, nutty, chocolate b) 7.0 sweet, oaky, anise note, more pleasant c) 1.010.0 sweet, grassy
 The amounts indicated refer to amounts of 1% alcoholic solutions (95% ethyl alcohol).



  2 The characteristics mentioned refer to the organoleptic properties of the compounds tested on tobacco and compared with unflavored tobacco.



   4,4,6-trimethylcyclohexa-2,5-diene-2-ol-1-one, a new alicyclic compound, can be prepared as follows:
 a) An equimolecular mixture of isophorone (13.82 g; 0.1 mol) and N-bromo-succinimide (17.80 g; 0.1 mol) in the presence of a trace of a, '-azodiisobutyronitrile a was refluxed in 500 ml of CCl4 for 15 min. After cooling, about 500 ml of petroleum ether (30-50 ° C) was added to the reaction mixture and the precipitated succinimide filtered off. Evaporation of the volatile parts gave 3,5,5-trimethyl4-bromo. crude cyclohex-2ene-one.



   NMR (CCl4): 1.16 (3H, s); 1.25 (3H, s); 2.11 (3H, s); 2.07 (1H, d,
J = 16cops); 2.53 (1H, d, J = 16 cps); 4.45 (1H, s); 5.78 (1H, s) 6 ppm.



   b) 43.4 g of 3,5,5-tnmethyl4-bromo-cyclohex-2-ene-one were added over 30 min to a solution maintained at 40 ° C of anhydrous trimethylamine-N-oxide (32 g) in 100 ml of anhydrous chloroform.



  The reaction was slightly exothermic and the temperature of the mixture was maintained at about 4550 ° C throughout the addition. After being kept at reflux for 20 min, the reaction mixture was cooled and poured onto 110 ml of H2SO4 diluted to 10%.

 

  The organic phase was then separated, washed with water (3x), 10% sodium carbonate (3x) and again with water (3x).



   Evaporation of the volatiles gave a residue which, on distillation, gave a product to eb. 47-60 C / 0.001 Torr. This product was taken up in petroleum ether (30-50 C), washed with a 5% aqueous solution of sodium carbonate (2 x) then with 2% caustic soda in water (5 x ). The caustic soda washes were acidified and immediately re-extracted with sulfuric ether.



   After washing, drying over MgSO4 and evaporation of the volatile parts, the ethereal extracts gave 8 g of crystalline product having a purity of 95%, according to the analysis carried out by gas chromatography.



   The following purification, carried out by sublimation at 70-80 "C / 10
Torr, gave 6 g of 4,4,6-trimethyl-cyclohexa-2,5-diene-2-ol-1 -one.



  The product gave a positive test by treatment with a solution of ferric chloride (violet blue coloration). F. 46 "C.



     IR (CCl4): 1630, 1650, 3440 cm-l
 UV: ta XH = 205, 249, 310 me = 5650, 7880, 2420 respective
 is lying)
 MS: M + = 152, m / e: 109
 NMR (CCl4): 1.27 (6H, s); 1.92 (3H, s); 5.97 (1H, pseudo d, J = about 2.5 cps); 6.34 (1H, m); 6.65 (1H, m); 8 ppm.



   Under the analytical conditions used, the structure of this compound was defined according to the formula
EMI2.1

 However, it is to be expected that under other conditions a keto-enolic balance will develop as follows:
EMI2.2

 keto-enol diketone
 If, instead of trimethylamine oxide, other oxides of a tertiary aliphatic or cycloaliphatic amine are used, analogous results are obtained. Likewise, as the halogenating agent, apart from the mentioned N-bromo-succinimide, halogenating agents capable of providing a positive halogen can be used.



   3,5,5-trimethyl-2,3-epoxy-cyclohexa-1,4-dione can be prepared as indicated below:
 2 ml of a 6N aqueous solution of NaOH were added over 15 min, at 15 ° C., to a mixture of 3.7 g of 3,5,5-trimethyl cyclohex-2-ene-1,4-dione and 8.3 ml of a 30% solution of hydrogen peroxide in 27 ml of methanol. The reaction mixture was then stirred for 3 hours at 20-25 ° C, then treated with water and extracted with l. 'ether. The combined organic extracts were washed with water until neutral, dried over MgSO4 and evaporated to dryness. In this way 3.33 g (82%) of the desired product is obtained, eb.



     40 "C / 0.001 Torr.



   IR: 1715cm-1; MS: M + = 168; m / e: 56
 NMR (CCl4): 1.05 (3H, s); 1.25 (3H, s); 1.50 (3H, s); 2.08 (1H, d,
J = 13 cps); 3.09 (1H, d, J = 13 cps); 3.47 (1H, s) 8 ppm.



   3,5,5-trimethylcyclohex-2-en-1,4-dione, used as a starting material in the above preparation, can be obtained according to the method described in Tetrahedron, Suppl. 8 / I, p. 1 (1966).

 

      CLAIM I
 Composition intended to strengthen, improve or modify the organoleptic properties of tobacco smoke, characterized in that it contains at least one of the compounds belonging to the following group of alicyclic derivatives: a) 3,5,5-trimethyl-2,3 -epoxycyclohexa-1,4-dione, b) 4,4,6-trimethylcyclohexa-2,5-diene-2-oî-1 -one, c) 3,5,5-trimethylcyclohex-2-en-2-ol -1 -one.



   CLAIM II
 Use of a composition as defined in claim I, as an agent for modifying the taste and aroma of tobacco smoke.

** ATTENTION ** end of DESC field can contain start of CLMS **.

Claims (1)

**ATTENTION** debut du champ CLMS peut contenir fin de DESC **. une pureté de 95%, suivant l'analyse effectuée par chromatographie en phase gazeuse. ** ATTENTION ** start of field CLMS can contain end of DESC **. a purity of 95%, according to the analysis carried out by gas chromatography. La purification suivante, effectuée par sublimation à 70-80" C/10 Torr, a donné 6 g de 4,4,6-triméthyl-cyclohexa-2,5-diène-2-ol-1 -one. The following purification, carried out by sublimation at 70-80 "C / 10 Torr, gave 6 g of 4,4,6-trimethyl-cyclohexa-2,5-diene-2-ol-1 -one. Le produit a donné un test positif par traitement avec une solution de chlorure ferrique (coloration bleu violette). F. 46"C. The product gave a positive test by treatment with a solution of ferric chloride (violet blue coloration). F. 46 "C. IR (CCl4): 1630, 1650, 3440 cm-l UV: ta XH=205, 249, 310 me =5650, 7880, 2420 respective ment) SM: M+=152,m/e: 109 RMN (CCl4): 1,27 (6H,s); 1,92 (3H,s); 5,97 (1H, pseudo d, J= environ 2,5 cps); 6,34 (1H,m); 6,65 (IH,m); 8 ppm. IR (CCl4): 1630, 1650, 3440 cm-l UV: ta XH = 205, 249, 310 me = 5650, 7880, 2420 respective is lying) MS: M + = 152, m / e: 109 NMR (CCl4): 1.27 (6H, s); 1.92 (3H, s); 5.97 (1H, pseudo d, J = about 2.5 cps); 6.34 (1H, m); 6.65 (1H, m); 8 ppm. Dans les conditions d'analyse utilisées, la structure de ce composé a été définie suivant la formule EMI2.1 Cependant, il faut s'attendre à ce que, dans d'autres conditions, un équilibre céto-énolique s'établisse comme suit: EMI2.2 céto-enol dicétone Si, à la place de l'oxyde de triméthylamine, on utilise d'autres oxydes d'une amine aliphatique ou cycloaliphatique tertiaire, des résultats analogues sont obtenus. De même, comme agent halo génant, on peut utiliser, à part le N-bromo-succinimide mentionné, des agents halogénants capables de fournir un halogène positif. Under the analytical conditions used, the structure of this compound was defined according to the formula EMI2.1 However, it is to be expected that under other conditions a keto-enolic balance will develop as follows: EMI2.2 keto-enol diketone If, instead of trimethylamine oxide, other oxides of a tertiary aliphatic or cycloaliphatic amine are used, analogous results are obtained. Likewise, as the halogenating agent, apart from the mentioned N-bromo-succinimide, halogenating agents capable of providing a positive halogen can be used. La 3,5,5-triméthyl-2,3-époxy-cyclohexa-1,4-dione peut être préparée comme indiqué ci-dessous: 2 ml d'une solution aqueuse de NaOH 6N ont été ajoutés durant 15 mn, à 15"C, à un mélange de 3,7 g de 3,5,5-triméthyl cyclohex-2-ène-1,4-dione et 8,3 ml d'une solution de péroxyde d'hydrogène à 30% dans 27 ml de méthanol. Le mélange réactionnel a ensuite été agité durant 3 heures à 20-25"C, puis traité avec de l'eau et extrait à l'éther. Les extraits organiques réunis ont été lavés à l'eau jusqu'à neutralité, séchés sur MgSO4 et évaporés, à sec. On obtient ainsi 3,33 g (82%) du produit désiré, éb. 3,5,5-trimethyl-2,3-epoxy-cyclohexa-1,4-dione can be prepared as indicated below: 2 ml of a 6N aqueous solution of NaOH were added over 15 min, at 15 ° C., to a mixture of 3.7 g of 3,5,5-trimethyl cyclohex-2-ene-1,4-dione and 8.3 ml of a 30% solution of hydrogen peroxide in 27 ml of methanol. The reaction mixture was then stirred for 3 hours at 20-25 ° C, then treated with water and extracted with l. 'ether. The combined organic extracts were washed with water until neutral, dried over MgSO4 and evaporated to dryness. In this way 3.33 g (82%) of the desired product is obtained, eb. 40"C/0,001 Torr. 40 "C / 0.001 Torr. IR: 1715cm-1; SM: M+=168; m/e: 56 RMN (CCl4): 1,05 (3H,s); 1,25 (3H,s); 1,50 (3H,s); 2,08 (1H,d, J= 13 cps); 3,09 (1H,d, J= 13 cps); 3,47 (1H,s) 8 ppm. IR: 1715cm-1; MS: M + = 168; m / e: 56 NMR (CCl4): 1.05 (3H, s); 1.25 (3H, s); 1.50 (3H, s); 2.08 (1H, d, J = 13 cps); 3.09 (1H, d, J = 13 cps); 3.47 (1H, s) 8 ppm. La 3,5,5-triméthylcyclohex-2-ène-1,4-dione, utilisée comme produit de départ dans la préparation ci-dessus, peut être obtenue selon le procédé décrit dans Tetrahedron, Suppl. 8/I, p. 1(1966). 3,5,5-trimethylcyclohex-2-en-1,4-dione, used as a starting material in the above preparation, can be obtained according to the method described in Tetrahedron, Suppl. 8 / I, p. 1 (1966). REVENDICATION I Composition destinée à renforcer, améliorer ou modifier les propriétés organoleptiques de la fumée de tabac, caractérisée en ce qu'elle contient au moins un des composés appartenant au groupe des dérivés alicycliques suivants: a) 3,5,5-triméthyl-2,3-époxycyclohexa-1,4-dione, b) 4,4,6-triméthylcyclohexa-2,5-diène-2-oî-1 -one, c) 3,5,5-triméthyîcyclohex-2-ène-2-ol-1 -one. CLAIM I Composition intended to strengthen, improve or modify the organoleptic properties of tobacco smoke, characterized in that it contains at least one of the compounds belonging to the following group of alicyclic derivatives: a) 3,5,5-trimethyl-2,3 -epoxycyclohexa-1,4-dione, b) 4,4,6-trimethylcyclohexa-2,5-diene-2-oî-1 -one, c) 3,5,5-trimethylcyclohex-2-en-2-ol -1 -one. REVENDICATION II Utilisation d'une composition telle que définie à la revendication I, comme agent modificateur du goût et de l'arôme de la fumée de tabac. CLAIM II Use of a composition as defined in claim I, as an agent for modifying the taste and aroma of tobacco smoke.
CH915671A 1971-01-19 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs CH549955A (en)

Priority Applications (45)

Application Number Priority Date Filing Date Title
CH34173A CH542591A (en) 1971-06-23 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs
CH915671A CH549955A (en) 1971-06-23 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs
DE2202066A DE2202066C2 (en) 1971-01-19 1972-01-17 Trimethylcyclohexane, hexene and hexadiene derivatives and their use in food and luxury foods, beverages or pharmaceutical preparations
DE19722202065 DE2202065A1 (en) 1971-01-19 1972-01-17 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs
CA132,661A CA991941A (en) 1971-01-19 1972-01-18 Flavoured tobacco composition
FR7201578A FR2175236A5 (en) 1971-01-19 1972-01-18
GB2389273A GB1380204A (en) 1971-06-23 1972-01-19 Ketonic flavouring agent for tobacco
GB2389373A GB1380205A (en) 1971-06-23 1972-01-19 Ketonic flavouring agent for tobacco
GB5474373A GB1380193A (en) 1971-06-23 1972-01-19 Cyclohexane derivative
GB2389073A GB1380202A (en) 1971-06-23 1972-01-19 Ketonic flavouring agent for tobacco
GB889573A GB1380199A (en) 1971-06-23 1972-01-19 Caryophyllene flavouring agents for tobacco
GB5474573A GB1380195A (en) 1971-06-23 1972-01-19 Cyclohexane derivative
NLAANVRAGE7200728,A NL170491C (en) 1971-01-19 1972-01-19 METHOD FOR AROMATIZING TOBACCO AND METHOD FOR MANUFACTURING SMOKING GOODS.
GB4591873A GB1380209A (en) 1971-06-23 1972-01-19 Phenolic flavouring agent for tobacco
GB889673A GB1380200A (en) 1971-06-23 1972-01-19 Ketonic flavouring agent for tobacco
GB259172A GB1380191A (en) 1971-06-23 1972-01-19 Cycloaliphatic flavouring agents
GB889373A GB1380197A (en) 1971-01-19 1972-01-19 Phenolic flavouring agent for tobacco
JP47007544A JPS519038B1 (en) 1971-01-19 1972-01-19
GB5474473A GB1380194A (en) 1971-06-23 1972-01-19 Cyclohexane derivative
GB2388973A GB1380201A (en) 1971-06-23 1972-01-19 Ketnonic flavouring agents for tobacco
GB889473A GB1380198A (en) 1971-06-23 1972-01-19 Heterocyclic ketone flavouring agents for tobacco
GB889273A GB1380196A (en) 1971-06-23 1972-01-19 Amide flavouring agents for tobacco
GB2389173A GB1380203A (en) 1971-06-23 1972-01-19 Ketonic flavouring agent for tobacco
GB889173A GB1380192A (en) 1971-06-23 1972-01-19 Cyclohexane derivative
FR7309593A FR2168121B1 (en) 1971-01-19 1973-03-16
US482776A US3920027A (en) 1971-01-19 1974-06-24 Flavored tobacco product
US05/482,512 US3989857A (en) 1971-01-19 1974-06-24 Flavoring phenol or phenol derivative containing food or feed with cycloaliphatic derivatives
CA226,238A CA1011758A (en) 1971-01-19 1975-05-05 Trimethyl-cyclohexene derivatives for flavouring tobacco
US05/586,385 US3937228A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,380 US3983885A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,310 US4029106A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,383 US4029108A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,387 US3981311A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,386 US4014350A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,384 US4031902A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,368 US4092989A (en) 1971-01-19 1975-06-12 Aromatic compositions
US05/586,382 US4029107A (en) 1971-01-19 1975-06-12 Aromatic compositions
JP12121675A JPS5310160B2 (en) 1971-06-23 1975-10-07
JP12121575A JPS5313719B2 (en) 1971-06-23 1975-10-07
JP12121875A JPS535759B2 (en) 1971-06-23 1975-10-07
JP50121219A JPS5179766A (en) 1971-06-23 1975-10-07 Shokuhin shiryo inryo oyobi yakugakuchoseibutsunokannoseio hensei kairyo mataha kojosaseruhoho
CA244,928A CA1004601A (en) 1971-01-19 1976-02-03 Flavoured tobacco composition
NLAANVRAGE8104372,A NL173706C (en) 1971-01-19 1981-09-23 METHOD FOR AROMATIZING TOBACCO AND METHOD FOR MANUFACTURING SMOKING GOODS.
NL8104371A NL8104371A (en) 1971-01-19 1981-09-23 Flavouring of tobacco prods. - with tri:methyl-cyclohexene derivs.
NLAANVRAGE8104373,A NL174219C (en) 1971-01-19 1981-09-23 METHOD FOR AROMATIZING TOBACCO AND METHOD FOR MANUFACTURING SMOKING GOODS.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH915671A CH549955A (en) 1971-06-23 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs

Publications (1)

Publication Number Publication Date
CH549955A true CH549955A (en) 1974-06-14

Family

ID=4348948

Family Applications (2)

Application Number Title Priority Date Filing Date
CH915671A CH549955A (en) 1971-01-19 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs
CH34173A CH542591A (en) 1971-06-23 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH34173A CH542591A (en) 1971-06-23 1971-06-23 Tobacco, food and beverages - aromatised by treatment with amides, esters, ketones and phenol derivs

Country Status (2)

Country Link
JP (2) JPS5310160B2 (en)
CH (2) CH549955A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS594372U (en) * 1982-06-30 1984-01-12 池田物産株式会社 Ceiling for interior of vehicles etc.

Also Published As

Publication number Publication date
JPS5170893A (en) 1976-06-18
JPS5310160B2 (en) 1978-04-11
JPS5170894A (en) 1976-06-18
JPS5313719B2 (en) 1978-05-12
CH542591A (en) 1973-10-15

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