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WO2025210260A1 - Procédés de production d'un extrait de tabac qui fournit une expérience semblable à celle d'une cigarette produite en usine - Google Patents

Procédés de production d'un extrait de tabac qui fournit une expérience semblable à celle d'une cigarette produite en usine

Info

Publication number
WO2025210260A1
WO2025210260A1 PCT/EP2025/059345 EP2025059345W WO2025210260A1 WO 2025210260 A1 WO2025210260 A1 WO 2025210260A1 EP 2025059345 W EP2025059345 W EP 2025059345W WO 2025210260 A1 WO2025210260 A1 WO 2025210260A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
methyl
ethyl
aerosol
tobacco
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.)
Pending
Application number
PCT/EP2025/059345
Other languages
English (en)
Inventor
Priscila Brasil de Souza Cruz
Samuel KAISER
Douglas William MENEZES FLORES
Camila Assis
Maurilio Gustavo NESPECA
Liliane Medianeira Favero Porte
Grace Jenske
Giovana DA SILVA PINHEIRO
Julia Lilian Gauderth de Azevedo
Liane Valadao VIEIRA BOKOWSKI
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.)
Nicoventures Trading Ltd
Original Assignee
Nicoventures Trading Ltd
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 Nicoventures Trading Ltd filed Critical Nicoventures Trading Ltd
Publication of WO2025210260A1 publication Critical patent/WO2025210260A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific 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
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • 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
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances
    • A24B15/243—Nicotine
    • 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
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24C—MACHINES FOR MAKING CIGARS OR CIGARETTES
    • A24C5/00—Making cigarettes; Making tipping materials for, or attaching filters or mouthpieces to, cigars or cigarettes
    • A24C5/01—Making cigarettes for simulated smoking devices

Definitions

  • the present invention relates to methods of producing a tobacco extract which provides a factory-made cigarette (FMC)-like experience, and to extracts formed using such methods.
  • the present invention also relates to a consumable for use in a non-combustible aerosol provision device, the consumable comprising the extract, and to a non-combustible aerosol provision system comprising the consumable and a non-combustible aerosol provision device.
  • Smoking articles such as cigarettes, cigars and the like burn tobacco during use to create tobacco smoke.
  • Alternatives to these types of articles release an inhalable aerosol or vapour by releasing compounds from a substrate material by heating without burning.
  • These may be referred to as non-combustible smoking articles, aerosol generating assemblies or non- combustible aerosol provision systems.
  • e-cigarette I tobacco heating product hybrid devices also known as electronic tobacco hybrid devices.
  • These hybrid devices contain a liquid source (which may or may not contain nicotine) which is vaporised by heating to produce an inhalable vapour or aerosol.
  • the device additionally contains a solid aerosolisable material (which may or may not contain a tobacco material) and components of this material are entrained in the inhalable vapour or aerosol to produce the inhaled medium.
  • vapour products which are handheld, battery-powered devices that heat a liquid (called an e-liquid) to produce an inhalable aerosol, commonly known as vapour.
  • e-liquid a liquid
  • vapour an inhalable aerosol
  • the compositions used in tobacco heated products and vaping platforms can also be used in oral products which are ingested by the consumer.
  • a method for forming a tobacco extract comprising:
  • the product of this method is a tobacco extract containing three or more of the key chemical markers described herein.
  • the tobacco material is provided in an aqueous solution, which may have a pH of from about 5 to about 7, such as from about 5.5 to about 6.5, from about 5.5 to about 6, or about 6.
  • the solution is heated during steps (ii) and (iii) to a temperature of from about 100°C to about 130°C, such as from about 105°C to about 125°C, from about 110°C to about 125°C, from about 115°C to about 125°C, from about 120°C to about 122°C, or about 121 °C.
  • the solvent is selected from the group consisting of pentane, diethyl ether and mixtures thereof. In embodiments, the solvent is a mixture of pentane and diethyl ether.
  • the period during which both the distillation step (ii) and the extraction step (iii) are carried out is from about 1 to about 20 hours, such as from about 1 to about 7 hours, from about 2 to about 7 hours, from about 4 to about 7 hours, from about 4.5 to about 6.5 hours, from about 5 to about 6 hours, or about 6 hours.
  • the invention provides a simultaneous distillation extraction (SDE) process for forming a tobacco extract, the method comprising: i) providing tobacco material; ii) subjecting the tobacco material to steam distillation; and iii) extracting one or more compounds from the tobacco material with a solvent; wherein distillation step (ii) and extraction step (iii) are carried out simultaneously; wherein the tobacco material is provided in an aqueous solution having a pH of from about 5 to about 7.
  • SDE simultaneous distillation extraction
  • the solution is heated during steps (ii) and (iii) to a temperature of from about 100°C to about 130°C, such as from about 105°C to about 125°C, from about 110°C to about 125°C, from about 115°C to about 125°C, from about 120°C to about 122°C, or about 121 °C.
  • the period during which both the distillation step (ii) and the extraction step (iii) are carried out is from about 1 to about 20 hours, such as from about 1 to about 7 hours, from about 2 to about 7 hours, from about 4 to about 7 hours, from about 4.5 to about 6.5 hours, from about 5 to about 6 hours, or about 6 hours.
  • a method for forming a tobacco extract comprising contacting tobacco with an extraction solvent under supercritical conditions to form a tobacco extract containing three or more key chemical markers.
  • the extraction solvent comprises, or is, supercritical CO2.
  • the process is performed at a pressure of from about 50 to about 500 bar, such as from about 100 to about 400 bar or from about 100 to about 300 bar.
  • the temperature during extraction may range from about 25°C to about 90°C, such as from about 30°C to about 70°C, or from about 40°C to about 60°C.
  • the invention provides a method for forming a tobacco extract, the method comprising contacting tobacco with a supercritical fluid (e.g. supercritical CO2) for
  • first pressure is from about 50 to about 200 bar (such as from about 80 to about 120 bar); and the second pressure is from about 200 to about 500 bar (such as from about 250 to about 400 bar or from about 250 to about 350 bar).
  • the temperature during extraction may range from about 25°C to about 90°C, such as from about 30°C to about 70°C, or from about 40°C to about 60°C.
  • the extract formed from any of these methods comprises at least 1 of the following compounds (hereinafter “List 1”): nicotine; 2-hydroxy-4-methyl-2-cyclopenten-1-one; quinic acid; sucrose; N-(1-deoxy-1-fructosyl)proline; 3,4-dimethyl-2(3H)-furanone; lipid peroxidation inhibitor 1 ; pseudooxynicotine and/or oxynicotine; 2-ethyl-quinoxaline; 1,2,3,4,5,6-hexahydro-7H-cyclopenta[b]pyridin-7-one; 2-ethyl-pyridine; scopoletin; 2-ethyl-5- methyl-pyridine; rutin; retinol; 2-methyl-3-butyl-pyrazine; megastigmatrienone; 3,5-di(1 ,1- dimethylethyl)-4-hydroxy-benzaldehyde; L-alpha-amino-1 H-pyrrole-1-hexanoi
  • the extract formed from any of these methods comprises at least 1 of the following compounds (hereinafter “List 2”): nicotine; pseudooxynicotine and/or oxynicotine; lipid peroxidation inhibitor 1; scopoletin; N-(1 -deoxy- 1-fructosyl)proline; sucrose; Type I sucrose ester - GV - IO; Type I sucrose ester - GIV - IO; chlorogenic acid; 1 , 2, 3, 4,5,6- Hexahydro-7H-cyclopenta[b]pyridin-7-one; L-alpha-amino-1 H-pyrrole-1 -hexanoic acid; retinol; quinic acid; Type I sucrose ester - Gill - IO; rutin; megastigmatrienone; 2-ethyl-5- methyl-pyridine; 16-hydroxy-hexadecanoicacid; Type III sucrose ester - GV - IO; and ferulic acid.
  • List 2
  • the extract formed from any of these methods comprises at least 1 of the following compounds (hereinafter “List 3”): 2-methoxy-phenol; p-cresol; furaneol; indole; 3- methyl-pentanoic acid; butanoic acid; 3-methyl-butanoic acid; D-limonene; acetophenone; 1- (4-methylphenyl)-ethanone; vanillin; 2,6-dimethoxy-phenol; benzaldehyde; benzeneacetic acid; 2-methyl-butanoic acid; pentanoic acid; hexanoic acid; acetic acid; 2-methyl-propanoic acid; and octanoic acid.
  • List 3 the following compounds
  • the extract formed from any of these methods comprises at least 1 of the following compounds (hereinafter “List 4”): 3-ethyl-2-hydroxy-2-cyclopenten-1-one; 5-methyl- 2-furancarboxaldehyde; propanoic acid; 3-methyl-pyridine; butanoic acid; 3-ethyl-pyridine; trimethyl-pyrazine; benzaldehyde; tiglic acid; 2-hydroxy-3-methyl-2-cyclopenten-1-one; acetophenone; 2-ethyl-phenol; 2-methoxy-phenol; furaneol; 4-ethyl-phenol; 3-ethyl-phenol; 1- (1 H-pyrrol-2-yl)-ethanone; 2-methoxy-4-vinylphenol; 4-ethyl-2-methoxy-phenol; octanoic acid; 2,6-dimethoxy-phenol; 2-methyl-propanoic acid; 3-methyl-butanoic acid; D-limonene; 2- acetyl
  • the extract formed from any of these methods comprises 30 or fewer compounds of List 4, such as 25 or fewer, 20 or fewer, 15 or fewer, 10 or fewer, or 5 or fewer.
  • the extract comprises 4 or fewer, 3 or fewer, 2 or fewer, or 1 or fewer of the compounds of List 4.
  • the extract comprises exactly 0, 1 , 2, 3, 4, or 5 of the compounds of List 4.
  • the extract comprises none of the compounds of List 4.
  • the extract formed from any of these methods comprises a total of at least 3 (e.g. at least 4, 5, 6, 7, 8, 9, 10, 11 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26,
  • the extract formed from any of these methods comprises a total of at least 4 (e.g. at least 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27,
  • the tobacco extract formed from any of these methods comprises some, but not all, of the compounds listed in List 1.
  • the tobacco extract formed from any of these methods comprises some, but not all, of the compounds listed in List 2.
  • the tobacco extract formed from any of these methods comprises some, but not all, of the compounds listed in List 3.
  • the tobacco extract formed from any of these methods comprises some, but not all, of the compounds listed in List 4.
  • the invention provides a tobacco extract formed from the methods described herein.
  • the invention provides a composition which comprises a tobacco extract as described herein.
  • the invention provides a composition which comprises a tobacco extract as described herein and at least one further compound, wherein said at least one further compound is one of the key chemical markers described herein (i.e. one of the compounds from Lists 1 , 2, 3 and 4).
  • the at least one further compound is not otherwise present in the tobacco extract (i.e. it must be added to the extract).
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from List 1.
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from List 2.
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from List 3.
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32 or 33) further compound(s) from List 4.
  • at least 1 such as at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32 or 33
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1 and 2. In embodiments, the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1 and 3. In embodiments, the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1 and 4. In embodiments, the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 2 and 3.
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1, 2 and 3. In embodiments, the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1, 2 and 4. In embodiments, the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1, 3 and 4. In embodiments, the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 2, 3 and 4.
  • the composition comprises a tobacco extract as described herein and at least 1 (such as at least 2, 3, 4 or 5) further compound(s) from each of Lists 1, 2, 3 and 4.
  • the composition or extract described herein comprises a total of from about 0.00001 to about 5 wt% of the compounds listed in Lists 1 , 2 and 3. In embodiments, the composition or extract comprises a total of from about 0.0001 to about 2 wt% of the compounds listed in Lists 1 , 2 and 3. In embodiments, the composition or extract comprises a total of from about 0.001 to about 1 wt% of the compounds listed in Lists 1 , 2 and 3. In embodiments, the composition or extract comprises a total of from about 0.005 to about 0.5 wt% of the compounds listed in Lists 1, 2 and 3.
  • the composition or extract described herein comprises a total of from about 0.00001 to about 5 wt% of the compounds listed in Lists 1 , 2, 3 and 4. In embodiments, the composition or extract comprises a total of from about 0.0001 to about 2 wt% of the compounds listed in Lists 1, 2, 3 and 4. In embodiments, the composition or extract comprises a total of from about 0.001 to about 1 wt% of the compounds listed in Lists 1, 2, 3 and 4. In embodiments, the composition or extract comprises a total of from about 0.005 to about 0.5 wt% of the compounds listed in Lists 1, 2, 3 and 4.
  • the composition is a solid, semi-solid (e.g. gel) or liquid. In embodiments the composition is a solid. In embodiments the composition is a gel. In embodiments the composition is a liquid. In embodiments, the composition is not an aerosol. In embodiments, the composition is not a gaseous composition. In embodiments, the composition is an aerosol-generating composition.
  • the aerosolgenerating composition may be a solid, semi-solid (e.g. gel) or liquid. In embodiments the composition is a solid. In embodiments the aerosol-generating composition is a gel. In embodiments the aerosol-generating composition is a liquid.
  • the composition is a composition for use in a non-combustible aerosol provision system.
  • the composition is a composition for use in an aerosol-free delivery system.
  • the composition is a composition for oral delivery of the compounds contained therein.
  • the total TSNA content of the compositions, extracts or materials described herein is less than about 800 ppb, less than about 500 ppb, less than about 200 ppb, less than about 100 ppb, less than about 50 ppb, less than about 20 ppb, or less than about 10 ppb. In embodiments there are no TSNAs in the compositions, extracts or materials described herein.
  • a consumable for use in a non-combustible aerosol provision device comprising an extract or a composition as described herein.
  • a non-combustible aerosol provision system comprising an extract, composition or consumable as described herein and a non-combustible aerosol provision device, the non-combustible aerosol provision device comprising an aerosol-generation device arranged to generate aerosol from the extract, composition or consumable when the extract, composition or consumable is used with the non-combustible aerosol provision device.
  • the aerosol-generation device may be a tobacco heating device, also known as a heat-not- burn device.
  • the aerosol-generation device may be a vaping device or e-cigarette.
  • an aerosol-free delivery system comprising an extract, composition or consumable as described herein.
  • Said aerosol-free delivery system may be configured to deliver the extract, composition or consumable to a user orally, nasally, transdermally or in another way without forming an aerosol, including but not limited to, lozenges, gums, patches, articles comprising inhalable powders, and oral products such as oral tobacco which includes snus or moist snuff.
  • Figure 3 is a perspective view of an oral product.
  • Sucrose esters are named by type (e.g. T1, Tl or Type 1 means Sucrose Ester Type I), group (e.g. GV or G5 means CsCeCs acids esterify the hydroxy groups on the glucose unit) and the number of double bonds on the acid groups (e.g. IO means zero double bonds, or saturated acid groups).
  • type e.g. T1, Tl or Type 1 means Sucrose Ester Type I
  • group e.g. GV or G5 means CsCeCs acids esterify the hydroxy groups on the glucose unit
  • the number of double bonds on the acid groups e.g. IO means zero double bonds, or saturated acid groups.
  • the tobacco extract formed from the processes described herein comprises exactly 3, 4, 5, 6, 7, 8, 9, 10, 11 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27,
  • the extract may optionally be combined (e.g. mixed) with one or more of the key chemical markers described herein.
  • the extract may first be analysed to determine which of the key chemical markers described herein is present or absent, and then adding one or more of the absent key chemical markers.
  • the one or more chemical markers combined with the extract may first be isolated or purified.
  • the tobacco extract may be obtained by techniques such as supercritical fluid extraction (SFE) or simultaneous distillation extraction (SFE).
  • SFE supercritical fluid extraction
  • SFE simultaneous distillation extraction
  • the tobacco used to form the extract may be Virginia tobacco, burley tobacco, oriental tobacco, or a combination thereof, and may be cured.
  • SDE provides a technique in which the steps of isolation and extraction of certain compounds from a sample can be achieved simultaneously.
  • the invention provides a simultaneous distillation extraction (SDE) process for forming a tobacco extract, the method comprising:
  • the invention provides a simultaneous distillation extraction (SDE) process for forming a tobacco extract, the method comprising: i) providing tobacco material; ii) subjecting the tobacco material to steam distillation; and iii) extracting one or more compounds from the tobacco material with a solvent; wherein distillation step (ii) and extraction step (iii) are carried out simultaneously; wherein the tobacco material is provided in an aqueous solution having a pH of from about 5 to about 7.
  • SDE simultaneous distillation extraction
  • the methods may comprise mixing a quantity of tobacco (e.g. ground tobacco) with water.
  • This solution may have a pH of from about 5 to about 7, such as from about 5.5 to about 6.5, from about 5.5 to about 6, or about 6. Glass beads may be added to prevent bumping.
  • the solution is then heated, for example to a temperature of from about 100°C to about 130°C, such as from about 105°C to about 125°C, from about 110°C to about 125°C, from about 115°C to about 125°C, from about 120°C to about 122°C, or about 121 °C.
  • the distillation step (ii) and extraction step (iii) are carried out simultaneously in one single step.
  • the SDE method described herein is carried out in just one single step.
  • an additional distillation and/or extraction step is excluded.
  • the entire SDE method i.e. distillation step (ii) and extraction step (iii) is carried out simultaneously in one single piece of apparatus with no additional processing prior to removal of the extracted product from the apparatus.
  • the solvent is a non-polar solvent. In some embodiments, the solvent is a polar solvent.
  • polar solvent refers to any solvent having a dielectric constant of greater than or equal to 15.
  • non-polar solvent refers to any solvent having a dielectric constant of less than 15.
  • the invention provides a simultaneous distillation extraction (SDE) process for forming a tobacco extract, the method comprising: i) providing tobacco material; ii) subjecting the tobacco material to steam distillation; and iii) extracting three or more key chemical markers from the tobacco material with a solvent; wherein distillation step (ii) and extraction step (iii) are carried out simultaneously; wherein the period during which both the distillation step (ii) and the extraction step (iii) are carried out is from about 4 to about 7 hours; wherein the solvent is a mixture of pentane and diethyl ether; and wherein the tobacco material is provided in an aqueous solution having a pH of from about 5 to about 7.
  • SDE simultaneous distillation extraction
  • the first period of time may be from about 0.5 to about 2 hours, such as about 1 hour.
  • the second period of time may be from about 0.5 to about 2 hours, such as from about 1 to about 2 hours, or about 1.5 hours.
  • the extract comprises a total of from 18 to 38 compounds from Lists 1 , 2 and 3. In embodiments, the extract comprises a total of from 25 to 37 compounds from Lists 1, 2 and 3. In embodiments, the extract comprises a total of from 30 to 36 compounds from Lists 1 , 2 and 3. In embodiments, the extract comprises a total of from 30 to 35 compounds from Lists 1 , 2 and 3.
  • the extract comprises 1 or more of the key sense markers (see List 1). In embodiments, the extract comprises at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 11 , at least 12, at least 13, at least 14, at least 15, at least 16, at least 17, at least 18, at least 19 or at least 20 of the key sense markers (see List 1).
  • the extract comprises 1 or more of the key taste markers (see List 2). In embodiments, the extract comprises at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 11 , at least 12, at least 13, at least 14, at least 15, at least 16, at least 17, at least 18, at least 19 or at least 20 of the key taste markers (see List 2).
  • the extract comprises 1 or more of the key flavour markers (see List 3). In embodiments, the extract comprises at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 11 , at least 12, at least 13, at least 14, at least 15, at least 16, at least 17, at least 18, at least 19 or at least 20 of the key flavour markers (see List 3).
  • the extract comprises 1 or more of the key smoke markers (see List 4). In embodiments, the extract comprises at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 11 , at least 12, at least 13, at least 14, at least 15, at least 16, at least 17, at least 18, at least 19 or at least 20 of the key smoke markers (see List 4).
  • the extract comprises at least 3 (e.g. at least 4, at least 5, at least 6, at least 8, at least 10 or at least 15) compounds from List 1, at least 3 (e.g. at least 4, at least 5, at least 6, at least 8, at least 10 or at least 15) compounds from List 2, at least 3 (e.g. at least 4, at least 5, at least 6, at least 8, at least 10 or at least 15) compounds from List 3 and optionally at least 3 (e.g. at least 4, at least 5, at least 6, at least 8, at least 10 or at least 15) compounds from List 4.
  • at least 3 e.g. at least 4, at least 5, at least 6, at least 8, at least 10 or at least 15
  • the compounds may be the same or different.
  • a single compound e.g. nicotine
  • the compounds must be different.
  • a single compound e.g. nicotine
  • any compound(s) included in the composition from List 2 and/or List 4 must be different to those already present in the composition from List 1.
  • the extract or composition comprises all of the compounds listed in Lists 1 , 2 and 3.
  • the extract or composition comprises all of the compounds listed in Lists 1 , 2, 3 and 4.
  • the extract or composition comprises a total of up to about 10 wt%, 5 wt%, 4 wt%, 3, wt%, 2 wt%, 1 wt% or 0.5 wt%, such as from about 0.0001 to about 2 wt%, from about 0.001 to about 1 wt% or from about 0.005 to about 0.5 wt% of the compounds as defined in List 1 .
  • the extract or composition comprises a total of up to about 10 wt%, 5 wt%, 4 wt%, 3, wt%, 2 wt%, 1 wt% or 0.5 wt%, such as from about 0.0001 to about 2 wt%, from about 0.001 to about 1 wt% or from about 0.005 to about 0.5 wt% of the compounds as defined in List 2.
  • the extract or composition comprises a total of up to about 10 wt%, 5 wt%, 4 wt%, 3, wt%, 2 wt%, 1 wt% or 0.5 wt%, such as from about 0.0001 to about 2 wt%, from about 0.001 to about 1 wt% or from about 0.005 to about 0.5 wt% of the compounds as defined in List 3.
  • the extract or composition comprises a total of up to about 10 wt%, 5 wt%, 4 wt%, 3, wt%, 2 wt%, 1 wt% or 0.5 wt%, such as from about 0.0001 to about 2 wt%, from about 0.001 to about 1 wt% or from about 0.005 to about 0.5 wt% of the compounds as defined in List 4.
  • the extract or composition comprises a total of up to about 10 wt%, 5 wt%, 4 wt%, 3, wt%, 2 wt%, 1 wt% or 0.5 wt%, such as from about 0.0001 to about 2 wt%, from about 0.001 to about 1 wt% or from about 0.005 to about 0.5 wt% of the compounds listed in Lists 1, 2 and 3.
  • the extract comprises at least 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; 2-methyl-3-butyl-pyrazine; and megastigmatrienone.
  • the extract comprises at least 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; 2-methyl-3-butyl-pyrazine; megastigmatrienone; 2- methyl-butanoic acid; and acetic acid.
  • the extract comprises at least nicotine; 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; 1,2,3,4,5,6-hexahydro-7H-cyclopenta[b]pyridin-7-one; 2-ethyl-pyridine; scopoletin; 2-ethyl-5-methyl-pyridine; 2-methyl-3-butyl-pyrazine; megastigmatrienone; solanesol; and 16-hydroxy-hexadecanoicacid.
  • the tobacco extract may be obtained using supercritical fluid extraction (SFE).
  • the extract comprises at least 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; retinol; 2-methyl-3-butyl-pyrazine; megastigmatrienone; Type I sucrose ester- GV - 10; Type III sucrose ester- GV - 10; 3-methyl- pentanoic acid; 3-methyl-butanoic acid; 1-(4-methylphenyl)-ethanone; 2-methyl-butanoic acid; pentanoic acid; hexanoic acid; acetic acid; and 2-methyl-propanoic acid.
  • the tobacco extract may be an extract of a blend of flue-cured Virginia, air-cured burley and sun-cured oriental tobacco.
  • the extract comprises at least 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; 2-methyl-3-butyl-pyrazine; megastigmatrienone; and L-alpha-amino-1 H-pyrrole-1-hexanoic acid.
  • the tobacco extract which be an extract of flue-cured Virginia tobacco.
  • the extract comprises at least nicotine; quinic acid; sucrose; N-(1-deoxy-1- fructosyl)proline; 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; 1,2,3,4,5,6-hexahydro-7H-cyclopenta[b]pyridin-7-one; 2-ethyl-pyridine; scopoletin; 2-ethyl-5- methyl-pyridine; rutin; 2-methyl-3-butyl-pyrazine; megastigmatrienone; L-alpha-amino-1 H- pyrrole-1 -hexanoic acid; solanesol; chlorogenic acid; 16-hydroxy-hexadecanoicacid; and ferulic acid.
  • the tobacco extract may be obtained using supercritical fluid extraction (SFE) and/or may be an extract of flue-cured Virginia tobacco.
  • SFE supercritical fluid extraction
  • the tobacco extract may be obtained using supercritical fluid extraction (SFE) and/or may be an extract of a blend of flue-cured Virginia, air-cured burley and sun-cured oriental tobacco.
  • SFE supercritical fluid extraction
  • the tobacco extract may be obtained using simultaneous distillation extraction (SDE) and/or may be an extract of flue-cured Virginia tobacco.
  • SDE simultaneous distillation extraction
  • the extract comprises at least 3,4-dimethyl-2(3H)-furanone; pseudooxynicotine and/or oxynicotine; retinol; 2-methyl-3-butyl-pyrazine; megastigmatrienone; L-alpha-amino-1 H-pyrrole-1-hexanoic acid; Type I sucrose ester - GV - IO; and Type III sucrose ester - GV - IO.
  • the tobacco extract may be obtained using simultaneous distillation extraction (SDE) and/or may be an extract of a blend of flue-cured Virginia, air-cured burley and sun-cured oriental tobacco.
  • SDE simultaneous distillation extraction
  • composition comprising a tobacco extract formed by the method of the invention, and at least one further key chemical marker, such as a key smoke marker (i.e. a compound from List 4).
  • a key smoke marker i.e. a compound from List 4
  • the composition comprises 1 or more (e.g. 1, 2, 3, 4, 5, 6, 7, 8,
  • compositions may comprise 1 or more (e.g. 1, 2, 3, 4, 5, 6, 7, 8, 9,
  • the aerosol-generating material is formed as a sheet.
  • the aerosol-generating material sheet may be incorporated into the non-combustible aerosol provision system or consumable in sheet form.
  • the aerosol-generating material sheet may be incorporated as a planar sheet, as a gathered or bunched sheet, as a crimped sheet, or as a rolled sheet (i.e. in the form of a tube).
  • the aerosol-generating material of these embodiments may be included in the system/consumable as a sheet, such as a sheet circumscribing a rod of aerosolisable material (e.g. tobacco).
  • the thickness stipulated herein is a mean thickness for the material.
  • the aerosol-generating material thickness may vary by no more than 25%, 20%, 15%, 10%, 5% or 1%.
  • the aerosol-generating material in sheet form may have sufficient tensile strength such that it can be wound onto, or unwound from, a bobbin without breakages.
  • the aerosol-generating material in sheet form has a tensile strength of greater than or equal to about 250 N/m.
  • the aerosol-generating material may have any suitable area density, such as from 30 g/m 2 to 120 g/m 2 .
  • the aerosol-generating material may have a mass per unit area of from about 80 to 120 g/m 2 , or from about 70 to 110 g/m 2 , or particularly from about 90 to 110 g/m 2 , or suitably about 100 g/m 2 (so that it will not readily separate when mixed with tobacco, such as cut rag tobacco).
  • Such area densities may be particularly suitable where the aerosolgenerating material is included in the consumable/system in sheet form, or as a shredded sheet (described further herein below).
  • the invention provides an aerosol-generating substrate or consumable comprising a carrier on which the aerosol-generating material is provided.
  • the aerosolgenerating material may be bonded or otherwise joined to the carrier.
  • the carrier functions as a support on which the aerosol-generating material layer forms, easing manufacture.
  • the carrier may provide tensile strength to the aerosol-generating material layer, easing handling.
  • the carrier may be magnetic. This functionality may be used to fasten the carrier to the non-combustible aerosol provision device in use, or may be used to generate particular aerosol-generating material shapes.
  • the aerosol-generating composition may comprise one or more magnets which can be used to fasten the material to an induction heater in use.
  • the carrier may be substantially or wholly impermeable to gas and/or aerosol. This prevents aerosol or gas passage through the carrier layer, thereby controlling the flow and ensuring it is delivered to the user. This can also be used to prevent condensation or other deposition of the gas/aerosol in use on, for example, the surface of a heater provided in an aerosol generating assembly. Thus, consumption efficiency and hygiene can be improved in some cases.
  • the aerosol-generating material may be laminated to a carrier, such as a paper sheet.
  • the layer of slurry may be formed on a carrier, such as a paper sheet.
  • surface roughness may contribute to the strength of bond between the aerosolgenerating material and the carrier.
  • the surface of the carrier facing away from the aerosol-generating material may be arranged in contact with the heater, and a smoother surface may provide more efficient heat transfer.
  • the carrier is disposed so as to have a rougher side abutting the aerosol-generating material and a smoother side facing away from the aerosol-generating material.
  • the carrier may be a paper-backed foil; the paper layer abuts the aerosol-generating material and the properties discussed in the previous paragraphs are afforded by this abutment.
  • the foil backing is substantially impermeable, providing control of the aerosol flow path.
  • a metal foil backing may also serve to conduct heat to the aerosolgenerating material.
  • the foil layer of the paper-backed foil abuts the aerosol-generating material.
  • the foil is substantially impermeable, thereby preventing water provided in the aerosol- generating material from being absorbed into the paper which could weaken its structural integrity.
  • the carrier is formed from or comprises metal foil, such as aluminium foil.
  • a metallic carrier may allow for better conduction of thermal energy to the aerosol-generating material.
  • a metal foil may function as a susceptor in an induction heating system.
  • the carrier comprises a metal foil layer and a support layer, such as cardboard.
  • the metal foil layer may have a thickness of less than 20 pm, such as from about 1 pm to about 10 pm, suitably about 5 pm.
  • the carrier may have a thickness of between about 0.010 mm and about 2.0 mm, suitably from about 0.015 mm, 0.02 mm, 0.05 mm or 0.1 mm to about 1.5 mm, 1.0 mm, or 0.5 mm.
  • One aspect of the invention provides a method of forming a composition as described herein, comprising combining or mixing the extract and any other components of the composition together.
  • a liquid composition of the invention may be formed by combining glycerol, propylene glycol and a tobacco extract as described herein, optionally together with other key chemical markers and/or other components of the composition such as water and any other actives and/or flavourants.
  • a method of forming a material e.g. an aerosol-generating material as described herein, wherein the method comprises
  • one or more of the additional key chemical markers are (instead or additionally) applied to the slurry during and/or after steps (b) and/or (c).
  • chemical markers which may first be isolated or purified
  • the disclosures herein relating to constituents of the aerosol-generating composition and aerosol-generating material apply equally to the slurry.
  • the slurry may comprise these constituents in any of the proportions given herein in relation to the composition of the aerosolgenerating composition and material.
  • the slurry is applied to a support.
  • the layer may be formed on a support.
  • a setting agent comprising a calcium source (such as calcium chloride or calcium citrate), may be added to a slurry containing alginate and/or pectin to form a calcium-crosslinked alginate/pectin gel.
  • a calcium source such as calcium chloride or calcium citrate
  • the slurry solvent consists essentially of or consists of water. In some examples, the slurry comprises from about 50 wt%, 60 wt%, 70 wt%, 80 wt% or 90 wt% of solvent (WWB).
  • Each of the pouches 101 encloses a composition according to the invention.
  • Each of said pouches 101 has dimensions making it suitable for insertion into the mouth of the user (buccal administration), e.g. a length or width in the order of 1-4 cm.
  • two or more interconnected pouches 101 have combined dimensions likewise making them suitable for insertion into the mouth (buccal administration), such that the user may accommodate multiple interconnected pouches 101 in their mouth.
  • a single pouch 101 may contain an amount of a composition less than what would be commonly used, e.g. less than what causes an effect/medical response in most individuals.
  • the user may choose to dispense more than one pouch, e.g.
  • the pouches 101 may more easily be stored/accommodated in the mouth, e.g. without risk of losing/swallowing. In fact, a single pouch 101 may be too small to most individuals, whereas two or more interconnected pouches would constitute a preferred size.
  • the pouches 101 may be made of a water-permeable material 103 allowing liquid/water, or saliva of the mouth, to soak the composition enclosed by said pouches 101 , thereby accelerating the release of components of said composition.
  • the water-permeable material 103 allows water and components dissolved therein to pass through, such that said components may be dissolved in the liquid or absorbed by the user, e.g. into the blood vessels through the mucosa/gums.
  • the water-permeable material 103 has a wet strength selected such that said material does not disintegrate once soaked with water/saliva, since such disintegration would cause the enclosed composition to enter the digestive system of the user, which may be harmful or not provide any effect at all.
  • the water- permeable material 103 is made of a textile or paper-like membrane.
  • a first cross-section A and a second cross-section B of the pouches 101 are highlighted by dashed lines, illustrating the inner volume/chamber 104 intended for accommodating the composition.
  • Each of said pouches 101 are divided by a separation section 102, e.g. formed by welding opposing sidewalls of the water-permeable material 103 together, whereby said separation section 103 may be considered a welding section.
  • Dashed lines C indicate a possible continuation of the product 100, whereby said product 100 may comprise more than two interconnected pouches 101 , and such that each of said pouches 101 are mutually interconnected to its neighbouring pouches by means of a separation section 102, and such that said pouches 101 extend in a row.
  • the composition (which may be for oral delivery) further comprises one or more additives selected from sweeteners, taste modifiers, salts, buffering agents, colorants, oral care additives, preservatives, disintegration aids, emulsifiers, preservatives and antioxidants.
  • the aerosol-former material discussed above may be used as a humectant in the compositions which may be for oral delivery.
  • the above disclosures for example those regarding the compounds in Lists 1 to 4, in relation to the aerosol-generating composition or aerosol-generating material for use in aerosol generation apply equally to this aspect of the invention.
  • the inventors have identified a range of compounds responsible for the overall sensory experience of smoking a traditional cigarette (sometimes called a factory made cigarette or FMC).
  • the compounds were identified by collecting and analysing the smoke produced from burning cigarettes.
  • HTS-HRMS High throughput screening coupled with high resolution mass spec
  • GC-MS data Specifically, compounds could be identified based on exact monoisotopic mass and isotopic pattern from HTS-HRMS data and from GC-MS mass spectra, as compared to reference MS libraries and reference compounds.
  • Human sensory assessment could be used to assign the individual chemicals to one of three categories or flavour dimensions, namely those responsible for the (1) sense, (2) taste, and (3) flavour of the cigarette smoke. Some compounds fall into more than one category or flavour dimension. For example, a single compound may be responsible for providing both a cigarettelike sense and taste.
  • any substitute composition can contain compounds from each of these three categories.
  • compounds from one category can be enough to provide a composition having a cigarette-like sense, taste or flavour, or to increase the cigarette-like sense, taste or flavour of a given composition.
  • a machine learning model was created, trained and validated using more than 1 ,000 samples that were previously accessed by human sensory panels, to determine for each compound whether it would enhance one or more of the flavour dimensions.
  • PLSR partial least squares regression
  • compounds were found that noticeably contributed to each flavour dimension (i.e. (1) sense, (2) taste, and/or (3) flavour), in particular those compounds having a VIP (variable importance of projection) higher than 1.
  • VIP variable importance of projection
  • chemical markers In total 324 chemical markers were identified as being associated with providing a cigarettelike experience. Over 250 chemical markers were found to enhance the cigarette-like sense, over 200 chemical markers were found to enhance the cigarette- 1 ike taste, and over 140 chemical markers were found to enhance the cigarette-like flavour.
  • the extracts were formed from either flue-cured Virginia tobacco (hereinafter called C38 tobacco) or a blend of flue-cured Virginia, air-cured burley and sun-cured oriental tobacco (hereinafter called Paris tobacco), using the SFE (supercritical fluid extraction) or SDE (simultaneous distillation extraction) process described below.
  • C38 tobacco flue-cured Virginia tobacco
  • Paris tobacco a blend of flue-cured Virginia, air-cured burley and sun-cured oriental tobacco
  • SFE supercritical fluid extraction
  • SDE sustaneous distillation extraction
  • 260g of ground tobacco was placed in a 1 L vessel and placed in the equipment for extraction using supercritical CO2 (1 kg/hr) as solvent. No co-solvent was used throughout the extraction process.
  • the pressure of system was set at 100 bar and a first fraction extracted for a period of 1 hour (the volatile extract).
  • the pressure was then increased to 300 bar and a second fraction extracted for a period of 1.5 hours (the non-volatile extract).
  • the temperature was maintained at 60 °C throughout the extraction process.
  • the two fractions or extracts were collected in two containers: one for the volatile fraction/extract and one for the non-volatile fraction/extract. Only the non-volatile fraction/extract was considered as the final extract.
  • the extracts were also analysed to determine whether the key chemical markers identified in Example 1 were present. The results are set out in the tables below.
  • the SFE extracts were found to generally have higher numbers of both the overall chemical markers and the key chemical markers. These extracts would therefore be expected to provide a more cigarette-like experience than the SDE extracts, when used to provide the flavour of a composition, for example in an aerosol-generating composition which could be used in a non-combustible aerosol provision system.
  • the C38 extract (Extract 1) has a slightly higher number of the key chemical markers.
  • the Paris extract (Extract 2) contains a higher number of key flavour markers.
  • Flavour could be considered to be the most important flavour dimension in a non-combustible aerosol provision system (e.g. in a vaping device), due to the volatility of the chemical markers or compounds associated with this flavour dimension.
  • Extract 2 might be expected to provide an overall improved cigarette-like experience than Extract 1.
  • HTS-HRMS High throughput screening coupled with high resolution mass spec
  • GC-MS data Specifically, compounds could be identified based on exact monoisotopic mass and isotopic pattern from HTS-HRMS data and from GC-MS mass spectra, as compared to reference MS libraries and reference compounds.
  • Some of the smoke markers are also key sense, taste and/or flavour markers. Where a marker is not present in the extract itself it may still be present in the smoke. For example, Extracts 1 and 2 contain nicotine (a key sense and taste marker) in the extract, but Extracts 3 and 4 did not. However, the smoke from Extracts 3 and 4 did contain nicotine. This further demonstrates that nicotine is a key marker, since it is either present in the extract or in the smoke, meaning that it will almost inevitably be present in any composition creating a cigarette- 1 ike experience.
  • Some of the other smoke markers are also similarly either present in each of the extracts (e.g. as a key flavour marker) or the smoke.
  • 2-methyl-propanoic acid is present in Extracts 2 and 4, but not Extracts 1 and 3.
  • 2-methyl-propanoic acid is present in the smoke produced from the tobacco of Extracts 1 and 3.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

La présente invention concerne des procédés de production d'un extrait de tabac qui fournit une expérience semblable à celle d'une cigarette produite en usine (FMC), et des extraits formés à l'aide de tels procédés. La présente invention concerne également un consommable destiné à être utilisé dans un dispositif de fourniture d'aérosol chauffé non brûlé, le consommable contenant l'extrait, et un système de fourniture d'aérosol chauffé non brulé comprenant le consommable et un dispositif de fourniture d'aérosol chauffé non brulé.
PCT/EP2025/059345 2024-04-04 2025-04-04 Procédés de production d'un extrait de tabac qui fournit une expérience semblable à celle d'une cigarette produite en usine Pending WO2025210260A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130239981A1 (en) * 2010-11-29 2013-09-19 Shanghai Tobacco Group Co., Ltd. Method for supercritical extraction of characteristic fragrant substances in different fragrant tobacco leaves
US20140299125A1 (en) * 2008-10-23 2014-10-09 Batmark Limited Inhaler
WO2015062983A2 (fr) 2013-10-29 2015-05-07 British American Tobacco (Investments) Limited Appareil permettant de chauffer une matière pouvant être fumée
WO2016135331A1 (fr) 2015-02-27 2016-09-01 British American Tobacco (Investments) Limited Cartouche, éléments et procédés de génération de milieu inhalable
US20210153543A1 (en) * 2017-05-15 2021-05-27 British American Tobacco (Investments) Limited Method of making a tobacco extract

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140299125A1 (en) * 2008-10-23 2014-10-09 Batmark Limited Inhaler
US20130239981A1 (en) * 2010-11-29 2013-09-19 Shanghai Tobacco Group Co., Ltd. Method for supercritical extraction of characteristic fragrant substances in different fragrant tobacco leaves
WO2015062983A2 (fr) 2013-10-29 2015-05-07 British American Tobacco (Investments) Limited Appareil permettant de chauffer une matière pouvant être fumée
WO2016135331A1 (fr) 2015-02-27 2016-09-01 British American Tobacco (Investments) Limited Cartouche, éléments et procédés de génération de milieu inhalable
US20210153543A1 (en) * 2017-05-15 2021-05-27 British American Tobacco (Investments) Limited Method of making a tobacco extract

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