WO2014005614A1 - Procédé pour aromatiser un produit à fumer - Google Patents

Procédé pour aromatiser un produit à fumer Download PDF

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Publication number
WO2014005614A1
WO2014005614A1 PCT/EP2012/062821 EP2012062821W WO2014005614A1 WO 2014005614 A1 WO2014005614 A1 WO 2014005614A1 EP 2012062821 W EP2012062821 W EP 2012062821W WO 2014005614 A1 WO2014005614 A1 WO 2014005614A1
Authority
WO
WIPO (PCT)
Prior art keywords
tobacco
pellitorine
mixtures
group
derivatives
Prior art date
Application number
PCT/EP2012/062821
Other languages
English (en)
Inventor
Gerhard Scheideler
Heike SIMON
Holger TEIWES
Rokiah MUNAJAT
Cher Weh KWIE
Lorraine YIP
Original Assignee
Symrise Ag
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 Symrise Ag filed Critical Symrise Ag
Priority to CN201280074332.3A priority Critical patent/CN104394718A/zh
Priority to PCT/EP2012/062821 priority patent/WO2014005614A1/fr
Publication of WO2014005614A1 publication Critical patent/WO2014005614A1/fr
Priority to HK15104366.1A priority patent/HK1203771A1/xx

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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
    • A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
    • A24B15/282—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by indirect addition of the chemical substances, e.g. in the wrapper, in the case
    • 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
    • A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
    • A24B15/283—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances
    • 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
    • A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00—Cigars; Cigarettes
    • A24D1/02—Cigars; Cigarettes with special covers
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive

Definitions

  • the present invention belongs to the area of smoking products and refers to a method for improved flavouring of tobacco and tobacco products by using pellitorine.
  • the flavour of smoking products consists of two parts: the aroma and the taste.
  • aro- ma ⁇ whereas the term " taste " is generally used to describe the sensory impact that is perceived via the mouth, especially the tongue.
  • the flavour sensation experienced upon consumption, especially the taste provides the final analysis of tobacco prior to consumption thereof.
  • Visual and olfactory (smell) signals already give a first indication but only after intake of the smoke into the mouth the final decision is made either to ingest or to reject the product.
  • Sweet taste is usually a signal that the product is safe (appetising) leading to ingestion of the tobacco.
  • Bitter and sour are usually experienced as repulsive taste sensations that can lead to rejection.
  • Temperature is another measure by which the smoking product is judged just as well as aching sensations like capsaicin (hot pepper) and certain chemicals (like carbon dioxide, menthol), also summarized as trigeminal effects.
  • tobacco used for the preparation of cigarettes is composed essentially of a mixture of different types of tobacco which gives the characteristic flavour and aroma that is desired in the tobacco smoke produced.
  • cigarettes currently manufactured usually contain mixtures of Virginia, Maryland or Kentucky tobacco in combination with oriental or Turkish tobacco.
  • flavouring substances and humectants as additives to these tobacco mixtures to further enhance the organoleptic properties thereof.
  • a huge number of very different chemical compounds have been proposed as flavourings for improving the organoleptic performance of a smoking product, like a cigarette or a cigar.
  • various derivatives of 6 to 12 membered aliphatic ring struc- tures are proposed in US 4,076,854, US 4,107,209 and US 4,75,251 (all I nternational Flavours and Fragrances I nc.).
  • EP 1517880 Bl (Sym- rise) describing a process for obtaining the isomer cis-pellitorine by transamidation of deca- dienoic acid esters with isobutylamine in the presence of a catalyst and the use of the product for flavouring for example oral care products and chewing gums.
  • EP 1562893 Bl (Sym- rise) covers the use of trans-pellitorine as a flavouring agent.
  • Compositions of cis- or trans- pellitorine and hesperitin are also known for improved sweetness (EP 1977655 Bl, Symrise).
  • Object of the present invention is a method of flavouring a smoking product by treating it with a working amount of pellitorine. More particularly, said smoking product is selected from the group consisting of cigarettes, cigarillos, cigars, snuff tobacco, chewing tobacco, water pipe tobacco, shisha tobacco, hookah tobacco, roll-your-own tobacco and electric cigarettes.
  • pellitorine provides a long-lasting, acid-free mouthwatering effect and increases salivation compared to a control level by up to 150 %. Also over longer storage times the flavour profile stays constant.
  • a major advantage linked to the present invention is that the treatment for example of tipping paper, especially Kretek tip- ping paper leads in deed to a more natural and sweet sugar-like perception.
  • Pellitorine (CAS 28836-52-7, FEMA 4148) stands for the isomeric forms of decadienoic acid- N-isobutylamide, which may be present as the ⁇ /is-form (2E, 4E) or the c/ ' s-form (2E, 4Z) or in the form of the (2Z, 4Z) or (2Z, 4E) isomers:
  • pellitorine The structure of pellitorine was first reported by Jacobson in JACS 71(1), p 366-367 (1949). It was originally extracted from the roots of Piper nigrum and was recently suggested by Cheng et al. for its anti-cancer properties [Molecules 15, p 2398-2404 (2010)] . The product is available in the market for example under the trademark Optaflow ® from Symrise.
  • Pellitorine can be administered directly to the tobacco rod, but also to the filters or the tipping papers.
  • the active is brought on the tobacco products, the filters or the pa- per in form of a solution in an organic solvent, such as for example Ci-C 4 aliphatic alcohols, preferably ethanol or (iso)propylalcohol, alkylene glycols, like e.g. ethylene glycol, propylene glycol, diethylene glycol or dipropylene glycol, triacetin and their mixtures.
  • the solutions may contain the Pellitorine in amounts of about 1 to about 25, preferably about 2 to about 20 and more preferably about 5 to about 15 % b.w.
  • pellitorine capsules it is also possible to treat the smoking products by pellitorine capsules.
  • the active is incorporated into the tobacco or into the filters.
  • the compositions are typically encapsulated by means of a solid covering material, which is preferably selected from starches, degraded or chemically or physically modified starches (in particular dextrins and maltodextrins), gelatins, gum arabic, agar-agar, ghatti gum, gellan gum, modified and non-modified celluloses, pullulan, curdlan, carrageenans, alginic acid, alginates, pectin, inulin, xanthan gum and mixtures of two or more of said substances.
  • a solid covering material which is preferably selected from starches, degraded or chemically or physically modified starches (in particular dextrins and maltodextrins), gelatins, gum arabic, agar-agar, ghatti gum, gellan gum, modified and non
  • the solid covering material is preferably selected from gelatin (preferred are pork, beef, chicken and/or fish gelatins and mixtures thereof, preferably comprising at least one gelatin with a bloom value of greater than or equal to 200, preferably with a bloom value of greater than or equal to 240), maltodextrin (preferably obtained from maize (corn), wheat, tapioca or potato, preferred maltodextrins have a DE value of 10 - 20), modified cellulose (for exam ple cellulose ether), alginates (for example Na-alginate), carrageenan (beta-, iota-, lambda- and/or kappa carrageenan), gum arabic, curdlan and/or agar-agar.
  • gelatin preferred are pork, beef, chicken and/or fish gelatins and mixtures thereof, preferably comprising at least one gelatin with a bloom value of greater than or equal to 200, preferably with a bloom value of greater than or equal to 240
  • Gelatin is preferably used, in particular, because of its good availability in different bloom values.
  • Particularly preferred, especially for oral use are seamless gelatin or alginate capsules, the covering of which dissolves very rapidly in the mouth or bursts when chewing. Production may take place, for example, as described in EP 0389700 Al, US 4,251,195, US 6,214,376, WO 2003 055587 or WO 2004 050069 Al.
  • microcapsules are understood to be spherical aggregates with a diameter of about 0.1 to about 5 mm which contain at least one solid or liquid core surrounded by at least one continuous membrane. More precisely, they are finely dispersed liquid or solid phases coated with film-forming polymers, in the production of which the polymers are deposited onto the material to be encapsulated after emulsification and coacervation or interfacial polymerization. I n another process, liq- uid active principles are absorbed in a matrix (“microsponge”) and, as microparticles, may be additionally coated with film-forming polymers.
  • microsponge a matrix
  • microscopically small capsules also known as nanocapsules
  • multiple-core aggregates also known as microspheres, which contain two or more cores distributed in the continuous membrane material.
  • single-core or multiple-core microcapsules may be surrounded by an additional second, third etc. membrane.
  • the membrane may consist of natural, semisynthetic or synthetic materials.
  • Natural membrane materials are, for example, gum arabic, agar agar, agarose, maltodextrins, alginic acid and salts thereof, for example sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysac- charides, such as starch or dextran, polypeptides, protein hydrolyzates, sucrose and waxes.
  • Semisynthetic membrane materials are inter alia chemically modified celluloses, more particularly cellulose esters and ethers, for example cellulose acetate, ethyl cellulose, hydroxy- propyl cellulose, hydroxypropyl methyl cellulose and carboxymethyl cellulose, and starch derivatives, more particularly starch ethers and esters.
  • Synthetic membrane materials are, for example, polymers, such as polyacrylates, polyamides, polyvinyl alcohol or polyvinyl pyr- rolidone.
  • microcapsules examples are the following commercial products (the membrane material is shown in brackets) Hallcrest Microcapsules (gelatin, gum arabic), Coletica Thalas- pheres (maritime collagen), Lipotec Millicapseln (alginic acid, agar agar), Induchem Unispheres (lactose, microcrystalline cellulose, hydroxypropylmethyl cellulose), Unicetin C30 (lactose, microcrystalline cellulose, hydroxypropylmethyl cellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar agar) and Kuhs Probiol Nanospheres (phospholipids).
  • the active principles are released from the microcapsules by mechanical, thermal, chemical or enzymatic destruction of the membrane, normally during the use of the preparations containing the microcapsules.
  • a shell is obtained by coazervation, precipitation or polycondensation of anionic and cationic polymers has been quite suitable for the formation of stable capsules.
  • a preferred process for the encapsulation of active principles according to the present invention is characterised in that it comprises the steps of
  • anionic and cationic polymers in steps (a) and (c) can be exchanged.
  • Gel formers are substances which are capable of forming gels in aqueous solution at temperatures above 40° C.
  • Typical examples of such gel formers are heteropolysaccharides and proteins.
  • Preferred thermogelling heteropolysaccharides are agaroses which may be present in the form of the agar agar obtainable from red algae, even together with up to 30% by weight of non-gel-forming agaropectins.
  • the principal constituent of agaroses are linear polysaccharides of Galactose and 3,6-anhydro-L-galactose with alternate 1,3- and 1,4-glycosidic bonds.
  • the heteropolysaccharides preferably have a molecular weight of 110,000 to 160,000 and are both odourless and tasteless. Suitable alternatives are pectins, xanthans (including xanthan gum) and mixtures thereof. Other preferred types are those which in 1% by weight aqueous solution still form gels that do not melt below 80° C. and solidify again above 40° C. Examples from the group of thermogelling proteins are the various gelatines.
  • alginic acid is a mixture of carboxyl-containing polysaccharides with the following idealized monomer unit:
  • the average molecular weight of the alginic acid or the alginates is in the range from 150,000 to 250,000.
  • Salts of alginic acid and complete and partial neutralization products thereof are understood
  • the alkali metal salts preferably sodium alginate ("algin") and the ammonium and alkaline earth metal salts.
  • Mixed alginates for example sodium/magnesium or sodium/calcium alginates, are particularly preferred.
  • carboxymethyl celluloses and anionic chitosan derivatives for example the carboxylation and above all succinylation products are also suitable for this purpose.
  • Chitosans are biopolymers which belong to the group of hydrocol- loids. Chemically, they are partly de-acetylated chitins differing in their molecular weights which contain the following - idealized - monomer unit:
  • chitosans are cationic biopolymers under these conditions.
  • the positively charged chitosans are capable of interacting with oppositely charged surfaces and are therefore used in cosmetic hair-care and body-care products and pharmaceutical preparations.
  • a 1 to 10 and preferably 2 to 5% by weight aqueous solution of the gel former, preferably agar agar, is normally prepared and heated under reflux.
  • a second aqueous solution containing the cationic polymer, preferably chitosan, in quantities of 0.1 to 2 and preferably 0.25 to 0.5% by weight and the active principle in quantities of 0.1 to 25 and preferably 0.25 to 10% by weight is added in the boiling heat, preferably at 80 to 100 ° C; this mixture is called the matrix.
  • the charging of the microcapsules with active principles may also comprise 0.1 to 25% by weight, based on the weight of the capsules.
  • water-insoluble constituents for example inorganic pigments
  • inorganic pigments may also be added at this stage to adjust viscosity, generally in the form of aqueous or aqueous/alcoholic dispersions.
  • emulsifiers and/or solubilisers to the matrix.
  • the matrix After its preparation from gel former, cationic polymer and active principle, the matrix optionally is very finely dispersed in an oil phase with intensive shearing in order to produce small particles in the subsequent encapsulation process. It has proved to be particularly advantageous in this regard to heat the matrix to temperatures in the range from 40 to 60° C while the oil phase is cooled to 10 to 20° C.
  • the actual encapsulation i.e. formation of the membrane by contacting the cationic polymer in the matrix with the anionic polymers, takes place in the third step.
  • the result- ing aqueous preparations generally have a microcapsule content of 1 to 10% by weight.
  • the solution of the polymers can be of advantage for the solution of the polymers to contain other ingredients, for example emulsifiers or preservatives.
  • microcapsules with a mean diameter of preferably 1 to 3 mm are obtained. It is advisable to sieve the capsules to ensure a uniform size distribution.
  • the microcapsules thus obtained may have any shape with- in production-related limits, but are preferably substantially spherical.
  • Pellitorine is administered at a working amount which means a concentration sufficient to achieve the desired performance.
  • pellitorine is added to the tobacco products in an amount of
  • the tobacco products are treated with mixtures of pellitorine and auxiliary agents, said auxiliary agents being selected from the group consisting of flavours, cooling agents, sweeteners, plant extracts and solvents.
  • Suitable flavours or flavourings include, but are not limited to, mint, such as peppermint and spearmint, chocolate, licorice, citrus and other fruit flavours, gamma octalactone, vanillin, ethyl vanillin, breath freshener flavours, spice flavours such as cinnamon, methyl salicylate, linalool, bergamot oil, geranium oil, lemon oil, and ginger oil.
  • Other suitable flavours may include flavour compounds selected from the group consisting of an acid, an alcohol, an ester, an aldehyde, a ketone, a pyrazine, combinations or blends thereof and the like.
  • compositions may also contain one or more flavours with a physiological cooling effect (cooling agents), which are preferably selected here from the following list: menthol and menthol derivatives (for example L-menthol, D-menthol, racemic menthol, isomenthol, neo- isomenthol, neomenthol) menthylethers (for example (l-menthoxy)-l,2-propandiol, (I- menthoxy)-2-methyl-l,2-propandiol, l-menthyl-methylether), menthylesters (for example menthylformiate, menthylacetate, menthylisobutyrate, menthyllactates, L-menthyl-L- lactate, L-menthyl-D-lactate, menthyl-(2-methoxy)acetate, menthyl-(2-methoxyethoxy- )acetate, menthylpyroglutamate), menthylcarbonates (for example
  • sweeteners which may be employed together with pelitorine include sugars, for example, monosaccharides of 5 or 6 carbon atoms, such as arabinose, xylose, ribose, glucose, mannose, galactose, fructose, dextrose, or sorbose or mixtures of two or more of the foregoing monosaccharides; disaccharides, for example, sucrose, such as cane or beet sugar, lactose, maltose or cellobiose; polysaccharides, such as partially hydrolyzed starch or dex- trin, as well as polyols, such as sorbitol, mannitol, xylitol, mixtures thereof and mixtures with one or more of the above sugars.
  • monosaccharides of 5 or 6 carbon atoms such as arabinose, xylose, ribose, glucose, mannose, galactose, fructose, dextrose, or
  • the mixtures may also contain an artificial sweetener, such as, for example, aspartame, cyclamate, or a saccharin or other sweetener as set out hereinafter, the artificial sweetener being present in an amount of from about 0 to about 0.5% by weight, and preferably, from about 0.05 to about 0.2% by weight.
  • an artificial sweetener such as, for example, aspartame, cyclamate, or a saccharin or other sweetener as set out hereinafter, the artificial sweetener being present in an amount of from about 0 to about 0.5% by weight, and preferably, from about 0.05 to about 0.2% by weight.
  • arti- ficial sweeteners which may be employed herein include sodium, calcium or ammonium saccharin salts, dihydrochalcones, rebaudiosides, mogrosides,glycyrrhizin, dipotassium glycyrrhizin, glycyrrhizic acid ammonium salt, L-aspartyl-L-phenylalamine methyl ester, (aspartame), the sodium or potassium salt of 3,4-dihydro-6-methyl-l,2,3-oxathiazine-4-one- 2,2-dioxide (Ace-sulfame-K), as well as extracts of Stevia rebaudiana (Stevioside), Richardella dulcifica (Miracle Berry), Dioscoreophyllum cumminsii (Serendipity Berry) or Luo Han Guo, cyclamate salts, and the like, or mixtures of any two or more of the above. Where long- lasting
  • Additional objects of the present invention are directed to a smoking product selected from the group consisting of cigarettes, cigarillos, cigars, snuff tobacco, chewing tobacco, water pipe tobacco, shisha tobacco, hookah tobacco, roll-your-own tobacco and electric ciga- rettes, flavoured with a working amount of pellitorine, and a tobacco rod, a filter or a tipping paper flavoured with a working amount of pellitorine.
  • Cigarette filters were treated with a composition comprising
  • the filters were used to make cigarettes and the flavoured cigarettes were compared to conventional unflavoured cigarettes (CI) and cigarettes flavoured by a composition where the pellitorine was replaced by the same amount of benzyl benzoate (C2) by a group consisting of 20 experienced consumers.
  • CI unflavoured cigarettes
  • C2 benzyl benzoate

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

L'invention concerne un procédé pour aromatiser un produit à fumer par traitement avec quantité utile de pellitorine.
PCT/EP2012/062821 2012-07-02 2012-07-02 Procédé pour aromatiser un produit à fumer WO2014005614A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201280074332.3A CN104394718A (zh) 2012-07-02 2012-07-02 一种烟产品调味的方法
PCT/EP2012/062821 WO2014005614A1 (fr) 2012-07-02 2012-07-02 Procédé pour aromatiser un produit à fumer
HK15104366.1A HK1203771A1 (en) 2012-07-02 2015-05-08 A method of flavouring a smoking product

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2012/062821 WO2014005614A1 (fr) 2012-07-02 2012-07-02 Procédé pour aromatiser un produit à fumer

Publications (1)

Publication Number Publication Date
WO2014005614A1 true WO2014005614A1 (fr) 2014-01-09

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ID=46456589

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/062821 WO2014005614A1 (fr) 2012-07-02 2012-07-02 Procédé pour aromatiser un produit à fumer

Country Status (3)

Country Link
CN (1) CN104394718A (fr)
HK (1) HK1203771A1 (fr)
WO (1) WO2014005614A1 (fr)

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