METHOD FOR EXTRACTION OF TOBACCO FLAVORS FROM AGED TOBACCO LEAVES

20250024877 ยท 2025-01-23

    Inventors

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    Abstract

    The present disclosure discusses a method for extracting flavors from tobacco leaves using one or more food grade solvents. In certain embodiments, the food grade solvents are either ethyl acetate, or ethanol, or a mixture of both.

    Claims

    1. A method of extracting tobacco flavors from tobacco plant material comprising: immersing tobacco material in a food grade solvent; wherein the food grade solvent is selected from the group consisting of ethyl acetate and ethanol, and a mixture of ethyl acetate and ethanol.

    2. The method of claim 1 wherein the food grade solvent is only ethyl acetate.

    3. The method of claim 1 wherein the food grade solvent is only ethanol.

    4. The method of claim 1 wherein the food grade solvent is a mixture of ethyl acetate and ethanol.

    5. The method of claim 1 wherein the tobacco material is immersed for thirty minutes or less.

    6. The method of claim 1 wherein the food grade solvent is at room temperature.

    7. The method of claim 1 wherein the food grade solvent is heated to about 60 degrees Celsius.

    8. The method of claim 1 wherein the food grade solvent is cooled to about 0 degrees Celsius.

    9. The method of claim 1 wherein the ratio of ethyl acetate to ethanol is between 1 to 0 and 0 to 1

    10. The method of claim 9 wherein the ratio of ethyl acetate to ethanol is 1 to 1.

    11. The method of claim 1 wherein the ethanol is 200 proof.

    12. The method of claim 1 wherein the resulting extract is a liquid having an anhydrous aqueous character.

    13. The method of claim 1 wherein the method is carried out without addition of any water to the food grade solvent.

    14. The method of claim 1 wherein the ratio of the tobacco material to the food grade solvent is 1 to 8, by weight.

    15. The method of claim 1 wherein the method is carried out without addition of any hydrocarbon solvent.

    16. The method of claim 15 wherein the method is carried out without the addition of any of hexane or toluene or dichloroethane or chloroform or isopropanol or methanol.

    17. The method of claim 1 further comprising at least partially evaporating the food grade solvent, whereby the resultant extract has a concentrated bolder, but less sweet, flavor.

    Description

    DETAILED DESCRIPTION OF THE EMBODIMENTS

    [0029] The description that follows is presented to enable one skilled in the art to make and use the present invention, and is provided in the context of a particular application and its requirements. Various modifications to the disclosed embodiments will be apparent to those skilled in the art, and the general principles discussed may be applied to other embodiments and applications without departing from the scope and spirit of the invention. Therefore, the invention is not intended to be limited to the embodiments disclosed, but the invention is to be given the largest possible scope which is consistent with the principles and features described herein.

    [0030] Embodiments disclosed herein relate to a method of extracting and isolating aroma components from the tobacco plant which comprises immersing aged tobacco leaves containing aroma components in a volatile food grade solvent for less than 30 minutes to achieve transfer of aroma components from the plant material. Further separating the food grade containing aroma components from the plant material is optional. If desirable, evaporating the food grade solvent will yield a bolder aromatic extract, because both ethyl acetate and or ethanol (volatile food grade solvents) are easily removed by distillation. But, if these volatile food grade solvents are not fully evaporated and remain present in a consumed tobacco product, they do impart some sweetness to the flavor. They have the rummy pineapple nuances delightful with the tobacco scent. In embodiments of the present disclosure, both solvents usage ratios to each other, ranging from, 1 to 1, or 1 to 0, or 0 to 1, or any ratios in between these values, can be adjusted based on aroma component targets.

    [0031] Virginia tobacco (Nicotiana tabacum) commonly grown in Virginia, Kentucky and Tennessee was used in our discovery. However, the extraction process disclosed herein can be applied to all tobacco leaves.

    [0032] Embodiments described herein include extracting components from tobacco materials using one single, or two combined food grade solvents, namely Ethyl acetate and 200 proof Ethanol. Use of a combination of both solvents are also possible resulting in different acceptable aroma profiles.

    [0033] The currently disclosed embodiments also completely avoid using water during the extraction process, for targeted hydrophobic compounds for extraction efficiency. As such, the disclosed tobacco extracts yield water-insoluble true tobacco flavor, with significant avoidance of water-soluble plant carbohydrates, sugars, and proteins. Even the plant fatty alcohols are significantly reduced with the disclosed methods, and this is advantageous because they do not contribute much to the aroma flavoring.

    [0034] As disclosed herein, a significant portion of the resultant extracts are aldehydes, ketones, and terpenes. A total 32 to 46 tobacco compounds were captured in each disclosed extraction, all dependent upon the solvent type/ratio used, and the selected temperature for the extraction.

    [0035] Thus, the tobacco desirable flavors are concentrated in situ, available for direct uses into cigarettes, cigars, e-cigarettes, and Vape products.

    [0036] Further evaporation of these solvents yields a more woody jam-like concentrated aroma.

    [0037] When extraction is carried out with biomass and volatile solvent at zero degrees C or lower, the plant alcohols, proteins and sugars remain mostly in their frozen state, all in the biomass. These unwanted non-aroma contributing materials do not interfere or dilute the targeted flavor components. Under such cold temperature, the surprising results were an increase in yield with decreased interference. In addition, the resulting extracts have an increase in both quantity, and types of lighter volatile aroma components.

    [0038] In comparison, extracting under high temperature of 60 C, yields more heavier leathery, woody, smoky notes.

    [0039] Example extraction combinations of the disclosed solvent(s), temperatures, and results of the present embodiments are as follows: [0040] Ethyl Acetate Room Temperature extraction: 30 mins, resulting in 46 natural aroma components; [0041] Ethanol Room Temperature extraction 30 mins, resulting in 38 natural aroma components; [0042] Ethyl acetate and Ethanol, 1 to 1 Mixture, Room Temperature extraction: 30 mins, resulting in 38 natural aroma components; [0043] Ethyl acetate and Ethanol, 1 to 1 Mixture, Zero Centigrade extractions: 10-20 mins, resulting in 32 natural aroma components; [0044] Ethyl acetate and Ethanol, 1 to 1 Mixture, Heated to 60 C: 30 mins, resulting in 36 natural aroma components.

    [0045] By the disclosed processes, even the solvents are natural food grade sustainable ingredients.

    [0046] Ethyl Acetate is made by heating ethanol with diluted acetic acid (vinegar).

    [0047] In another embodiment, the tobacco extract can be optimized according to desired aroma flavor by varying the extraction medium and/or temperature.

    [0048] All aroma flavor extracts processed by this method retain in independent liquid form until it is incorporated in the products. Since the disclosed extracts are water-free, they are easily incorporated into tobacco leaves for cigarettes/cigars. Also, the disclosed extracts are freely miscible in any Vape vehicles due to compatibility of extraction with Vape solvent glycol bases.

    [0049] Beyond direct addition of the flavors into cigarette, cigars, e-cigarettes, and Vape products, these flavors can be also use in paper packaging, such as cigarette filter additives. For example, the flavor and aromatic components can be incorporated into low density polyethylene and formed into strands, and then incorporated into cigarette filters as described in U.S. Pat. No. 4,281,671 to Bynre et al and 4,862,905 to Green, Jr., et al.

    [0050] The tobacco-derived components resulting from the present embodiments also are useful as cigarette wrapper additives; or as additives to the inner regions of cigarette packages (e.g., within a paper/foil laminate of cigarette package or within a low-density polyethylene film which is placed within a cigarette package) to provide a desirable aroma effect. This is one advantage of water-free extracted components. They can be infused in paper and plastics.

    [0051] In trying to optimize one extraction method, surprisingly Applicant has discovered five (5) workable processes. These five extraction processes yield five distinctly acceptable aroma flavors, each with their own flavor profile characteristics. In addition, solvent carrier evaporation is optional, dependent upon flavor intensity preference or solvent sweetness preferences. When the solvent carriers of the presently disclosed embodiments are evaporated, the resulting extracts have another five (5) bolder jam-like combinations. These ten (10) flavoring combinations can then be mixed to produce 20-30 acceptable tobacco flavors.

    For Example:

    [0052] Applicant discovered Zero degrees cold extraction retains more volatile lower molecular weight tobacco compounds. These compound mostly simple terpenes partitioning into the extraction medium without loses into atmosphere. [0053] The extraction of volatile compounds which impart flavor notes to tobacco products is challenging. The sample preparation and the isolation of the volatile fraction in extraction is often tedious. The volatile mixture in the biomass is often sequestered by plants fatty alcohols and fatty acids. [0054] This is because these volatile flavor molecules are lipophilic species and their affinity to fat matrix is high. [0055] However, surprisingly at cold temperature and Room temperature these plant alcohols and fatty acids are in their respective waxy state thus allowing the volatile compounds to partition out of them into the Ethyl acetate/Ethanol medium. [0056] The volatile compound extracted are: Alpha pinene, Limonene, Linalool, Nonanal Benzyl acetate, Benzyl cinnamate, Carvacrol, Ethyl toluene, Mesitylene, Pseudocumene, Cymene, Methyl Benzoate. [0057] They contribute to fresh sweet sharp pungent aromatic plant aroma.

    For Example:

    [0058] 60 C hot extraction yield bold, aromatic notes consistent with heavier molecular weight compounds with higher volatility and higher boiling points. [0059] The compounds are: Neophytadiene 10 times higher than OC extraction. Phytol, Cotinine, -4,8,13-Duvatriene-1,3-diol were 5 to 10 times higher than OC cold extraction. Ketones such as Solanone, Undecanone, and Phytone were also 3 to 4 folds higher when extracted at 60 C. [0060] Resulting in Bolder tobacco flavor at 60 C. [0061] These compounds provide the earthy woody, leathery, typical tobacco jam-like aroma.
    Common Components Resulting by these 5 Extraction Methods Include: [0062] RT 25C Ethyl acetate, 46 natural aroma components, including: [0063] -Pinene Monoterpene [0064] 3-Methylvaleric acid Aliphatic acid [0065] para-Cymene Monoterpene [0066] Limonene Monoterpene [0067] 1,8-Cineole Monoterpenic ether [0068] Benzyl alcohol Simple phenolic [0069] 1-Methyl-2-pyrrolidinone Alkaloid [0070] Linalool Monoterpenic alcohol [0071] Nonanal Aliphatic aldehyde [0072] 3-Acetylpyridine Alkaloid [0073] Dodecane Alkane [0074] Methyl nonanoate Aliphatic ester [0075] Phenylacetic acid Phenolic acid [0076] 2-Undecanone Aliphatic ketone [0077] Carvacrol Monoterpenic alcohol [0078] Nicotine Alkaloid [0079] (E)-Solanone Terpenic ketone [0080] Tetradecane Alkane [0081] Myosmine Alkaloid [0082] N-Methylnicotinamide Alkaloid [0083] 4-Oxo-4-(3-pyridyl)butanal Alkaloid [0084] (E)-Norsolanadione Terpenic ketone [0085] Pentadecane Alkane [0086] Dipyridyl isomer Alkaloid [0087] Dihydroactinidiolide isomer II Aliphatic lactone [0088] Hexadecane Alkane [0089] Cotinine Alkaloid [0090] Benzyl benzoate Phenolic ester [0091] Isopropyl myristate Aliphatic ester [0092] Neophytadiene Diterpene [0093] Phytone Terpenic ketone [0094] Palmitic acid Aliphatic acid [0095] Isopropyl palmitate Aliphatic ester [0096] SclareolideTerpenic lactone [0097] Benzyl (E)-cinnamate Phenylpropanoid ester [0098] Phytol Diterpenic alcohol [0099] Stearic acid Aliphatic acid [0100] -4,8,13-Duvatriene-1,3-diolDiterpenic alcohol [0101] Hexacosane Alkane [0102] Heptacosane Alkane [0103] Octacosane Alkane [0104] Nonacosane Alkane [0105] Triacontane Alkane [0106] Untriacontane Alkane [0107] Dotriacontane Alkane [0108] Tritriacontane Alkane [0109] RT 25C Ethanol, 38 natural aroma components, including: [0110] Butyl acetate Aliphatic ester [0111] para-Ethyltoluene Simple phenolic [0112] meta-Ethyltoluene Simple phenolic [0113] Mesitylene Simple phenolic [0114] Pseudocumene Simple phenolic [0115] meta-Cymene Monoterpene [0116] para-Cymene Monoterpene [0117] Methyl benzoate Phenolic ester [0118] 2-Undecanone Aliphatic ketone [0119] Nicotine Alkaloid [0120] (E)-Solanone Terpenic ketone [0121] Nornicotine Alkaloid [0122] Myosmine Alkaloid [0123] N-Methylnicotinamide Alkaloid [0124] 4-Oxo-4-(3-pyridyl)butanal Alkaloid [0125] (E)-Norsolanadione Terpenic ketone [0126] Anatabine Alkaloid [0127] Dipyridyl isomer Alkaloid [0128] Cotinine Alkaloid [0129] Benzyl benzoate Phenolic ester [0130] Neophytadiene Diterpene [0131] Phytone Terpenic ketone [0132] Palmitic acid Aliphatic acid [0133] 10,18-Bisnorabieta-5,7,9(10),11,13- [0134] pentaene [0135] Norditerpene [0136] Phytol Diterpenic alcohol [0137] Stearic acid Aliphatic acid [0138] -4,8,13-Duvatriene-1,3-diol Diterpenic alcohol [0139] Tetracosane Alkane [0140] Pentacosane Alkane [0141] Hexacosane Alkane [0142] Heptacosane Alkane [0143] Octacosane Alkane [0144] Nonacosane Alkane [0145] Triacontane Alkane [0146] Untriacontane Alkane [0147] Tritriacontane [0148] Ethyl acetate, Ethanol 1 to 1 Mixture, RT 25 C, 38 natural aroma components, including: [0149] Butyl acetate Aliphatic ester [0150] para-Ethyltoluene Simple phenolic [0151] meta-Ethyltoluene Simple phenolic [0152] Mesitylene Simple phenolic [0153] Pseudocumene Simple phenolic [0154] meta-Cymene Monoterpene [0155] para-Cymene Monoterpene [0156] Benzyl alcohol Simple phenolic [0157] ortho-Cymene Monoterpene [0158] Methyl benzoate Phenolic ester [0159] 2-Undecanone Aliphatic ketone [0160] Nicotine Alkaloid [0161] (E)-Solanone Terpenic ketone [0162] Nornicotine Alkaloid [0163] Myosmine Alkaloid [0164] N-Methylnicotinamide Alkaloid [0165] 4-Oxo-4-(3-pyridyl)butanal Alkaloid [0166] (E)-Norsolanadione Terpenic ketone [0167] Anatabine Alkaloid [0168] Dipyridyl isomer Alkaloid [0169] Cotinine Alkaloid [0170] Benzyl benzoate Phenolic ester [0171] Neophytadiene Diterpene [0172] Phytone Terpenic ketone [0173] Palmitic acid Aliphatic acid [0174] 10,18-Bisnorabieta-5,7,9(10),11,13-Pentaene Norditerpene [0175] Phytol Diterpenic alcohol [0176] Stearic acid Aliphatic acid [0177] -4,8,13-Duvatriene-1,3-diol Diterpenic alcohol [0178] Tetracosane Alkane [0179] Pentacosane Alkane [0180] Hexacosane Alkane [0181] Heptacosane Alkane [0182] Octacosane Alkane [0183] Nonacosane Alkane [0184] Triacontane Alkane [0185] Untriacontane Alkane [0186] Tritriacontane [0187] Ethyl acetate, Ethanol, 1 to 1 Mixture, cold 0 C, 32 natural aroma components, including: [0188] Butyl acetate Aliphatic ester [0189] para-Ethyltoluene Simple phenolic [0190] meta-Ethyltoluene Simple phenolic [0191] Mesitylene Simple phenolic [0192] Pseudocumene Simple phenolic [0193] meta-Cymene Monoterpene [0194] para-Cymene Monoterpene [0195] Methyl benzoate Phenolic ester [0196] Nicotine Alkaloid [0197] (E)-Solanone Terpenic ketone [0198] Nornicotine Alkaloid [0199] Myosmine Alkaloid [0200] 4-Oxo-4-(3-pyridyl)butanal Alkaloid [0201] (E)-Norsolanadione Terpenic ketone [0202] Anatabine Alkaloid [0203] Dipyridyl isomer Alkaloid [0204] Cotinine Alkaloid [0205] Benzyl benzoate Phenolic ester [0206] Neophytadiene Diterpene [0207] Phytone Terpenic ketone [0208] Palmitic acid Aliphatic acid [0209] Phytol Diterpenic alcohol [0210] Stearic acid Aliphatic acid [0211] -4,8,13-Duvatriene-1,3-diol Diterpenic alcohol [0212] Tetracosane Alkane [0213] Pentacosane Alkane [0214] Hexacosane Alkane [0215] Heptacosane Alkane [0216] Nonacosane Alkane [0217] Triacontane Alkane [0218] Untriacontane Alkane [0219] Tritriacontane [0220] Ethyl acetate, Ethanol, 1 to 1 Mixture, hot 60C, 36 natural aroma components, including: [0221] Butyl acetate Aliphatic ester [0222] para-Ethyltoluene Simple phenolic [0223] meta-Ethyltoluene Simple phenolic [0224] Mesitylene Simple phenolic [0225] Pseudocumene Simple phenolic [0226] meta-Cymene Monoterpene [0227] para-Cymene Monoterpene [0228] Methyl benzoate Phenolic ester [0229] 2-Undecanone Aliphatic ketone [0230] Nicotine Alkaloid [0231] (E)-Solanone Terpenic ketone [0232] Nornicotine Alkaloid [0233] Myosmine Alkaloid [0234] N-Methylnicotinamide Alkaloid [0235] 4-Oxo-4-(3-pyridyl)butanal Alkaloid [0236] (E)-Norsolanadione Terpenic ketone [0237] Anatabine Alkaloid [0238] Dipyridyl isomer Alkaloid [0239] Cotinine Alkaloid [0240] Benzyl benzoate Phenolic ester [0241] Neophytadiene Diterpene [0242] Phytone Terpenic ketone [0243] Palmitic acid Aliphatic acid [0244] 10,18-Bisnorabieta-5,7,9(10),11,13-Pentaene Norditerpene [0245] Phytol Diterpenic alcohol [0246] Stearic acid Aliphatic acid [0247] -4,8,13-Duvatriene-1,3-diol Diterpenic alcohol [0248] Tetracosane Alkane [0249] Pentacosane Alkane [0250] Hexacosane Alkane [0251] Heptacosane Alkane [0252] Octacosane Alkane [0253] Nonacosane Alkane [0254] Triacontane Alkane [0255] Untriacontane Alkane [0256] Tritriacontane

    [0257] In another example, the disclosed process was performed with room temperature Ethyl acetate. The flavonoid-rich natural products exert a wide range of pharmacological properties. This investigation aimed at obtaining compounds from tobacco leaves with flavonoids from Aldehydes to Ketones to Terpenes. All can be used for flavoring and pharmaceutical applications. Extraction with food grade medium was employed resulting in assortment of natural compounds. A total of 47 natural compounds found. They can be regarded as potential flavors, flavor enhancers, and even biopharmaceuticals. Some can be classified as Tobacco essential oils, generally different from other essential oils, which usually consist of several special aroma compounds not found in other plants. Tobacco essential oils can be used in flavors, even perfumes and smoking cessation products. They can be grouped into general classes providing the following taste and smell profiles. [0258] AldehydesCherry, Sweet, Vanilla [0259] KetonesButter, Caramel [0260] EstersGreen, Fruity, Honey [0261] TerpenesCitrus, Herbaceous, Woody [0262] LactonesSweet, Mango/peach

    [0263] Other more specialized compounds found by this analysis in tobacco leaves are: [0264] Solanone, Neophytadiene, and Norsolanadione. They provide the aromatic smoothness in taste. [0265] Solanone is a compound that give tobacco its smell & taste characters. [0266] Solanesol, a tri-sesquiterpenoid alcohol is present in many botanical and biological species. It is the starting material for synthesis of Vitamin K2, Vitamin E, Coenzyme Q9, Coenzyme Q10 (Colowick and Kaplan, 1975) and anti-cancer drug potentiating agents like N-solanesyl-N,N1-bis(3,4-dimethoxybenzyl)ethylenediamine (Suzuki et al., 1990 and Tomida et al., 1990). Tobacco is the richest source of solanesol, which has excellent prospects as drug intermediate. [0267] Neophytadiene is a flavor enhancer in that it may act as a flavor carrier by entrapping volatiles in the tobacco smoke aerosol. [0268] Applicant has also found 3-Acetyl pyridine (popcorn), Limonene (lemon), Carvacrol (medicinal), Benzyl Benzoate (Sweet Balsamic), 3-Methyl Valeric acid (Green sour), Sclareolide (Woody), and Nonanal (Floral rose). [0269] The two biological actives found are, Duvatriene 1,3 diol (a known mold inhibitor), and Heptacosane (a known insect pheromone). They have agricultural/pharmaceutical implications.

    [0270] In flavoring, the amount of these compounds can be added to a tobacco product depends on the desired function. The amount added to a tobacco composition can vary but will typically range from about 5 ppm to about 5 weight percent for flavoring, or as active molecule carriers to control absorption, 1% to 5% in pharmaceutical preparations.

    [0271] Now Applicant can now infuse natural products with an unmatched and customized natural flavoring. [0272] 1) RT 25C Ethyl acetate: 46 natural aroma components; 2) RT 25C Ethanol: 38 natural aroma components; [0273] 3) Ethyl acetate Ethanol 1 to 1 Mixture RT 25 C: 38 natural aroma components; [0274] 4) Ethyl acetate Ethanol 1 to 1 Mixture cold 0 C: 32 natural aroma components; [0275] 5) Ethyl acetate Ethanol 1 to 1 Mixture hot 60 C: 36 natural aroma components.

    Discovery of 5 Groups of Natural Tobacco Aroma-Flavors:

    TABLE-US-00001 Extracted Flavor component Aroma flavor contribution per Extraction Extraction Technique description analysis Group 1 1)RT 25 C. Ethyl acetate Fresh, floral, sweet, Alpha pinene 46 natural aroma woody, fruity, caramel Limonene components with some grassy and a Linalool hint of pineapple notes Nonanal Benzyl acetate Benzyl cinnamate Carvacrol Group 2 2)RT 25 C. Ethanol: 38 Mossy, Green leafy, No Ethyl toluene natural aroma dried fruit, floral with detected, mostly components apple, hint of honey- alkaloid and alkane. tea, some tart Less high molecular sharpness weight aroma contributing compounds thus lighter scent. Cymene, Myosmine and Phytone present. Simple phenolics and terpenes Less Neophytadiene, Solanone, Undecanone,and Phytone Group 3 3)Ethyl acetate Ethanol Dry wood, musk, More 1 to 1 Mixture RT 25 amber notes, powdery Neophytadiene C., 38 natural aroma sweet with hint of Solanone components green grapes. Present contributing to typical tobacco aroma. Cymene, Pseudocumene also present Group 4 4)Ethyl acetate Ethanol Grassy leafy, Aroma dominated by 1 to 1 Mixture cold 0 herbaceous, hay, Ethyl toluene and C., 32 natural aroma ambrosial, resinous, Pseudocumene components with some plum resin Thus sweet pungent & notes. sharp characteristics. Less Neophytadiene Solanone Undecanone Phytone Group 5 5)Ethyl acetate Ethanol Bold, cigar like, sweet Highest in 1 to 1 Mixture hot 60 C., jam-like, woody, hay, Neophytadiene 36 natural aroma touch of rum, slightly Solanone components. spicy. Undecanone Phytone Highest bolder levels. More leathery, woody, smoky notes.

    [0276] The disclosed five groups above also suggest different flavor intensities, specifically:

    Flavor Intensity Comparison of the 5 Groups:

    [0277] 5>1>3>4>2 showing heat and ethyl acetate work synergistically. Ethyl Acetate is an excellent solvent for broad spectrum extraction of all aroma components.

    Earthy Woody Note Intensity Comparison of the 5 Groups:

    [0278] 5>1>3>4>2 Showing typical tobacco earthy woody notes preferred heated temperature to partition. Especially in heated temperature yield higher boiling point compounds.

    Creamy Floral Note Intensity Comparison of the 5 Groups:

    [0279] 1>3>4>2>5 Showing the fresh lighter notes can be captured at lower temperature. Surprisingly, room temperature yields best results. Possibly due to low vapor pressure of volatile components.

    [0280] In our attempt to optimize one extraction procedure for one aroma flavor, surprisingly we have discovered 5 distinctly different aroma flavor profiles. All are suitable for flavoring. These flavor profiles range from Bold woody to Fresh floral fruity. All have a grassy hay component in the profile typical of all tobaccos.

    [0281] This discovery can provide an assortment of natural nuances in flavoring, and will eliminate the need to rely on synthetic additives.

    [0282] The table below describes the Classes of Volatile and Nonvolatile flavoring compounds from tobacco captured by the disclosed methods:

    TABLE-US-00002 Monoterpenes Alpha-pinene, limonene, meta-Cymene para-Cymene Diterpenes Neophytadiene Monoterpenols Linalool Aldehydes Nonanal Ketones Solanone, Norsolanadione, 2-Undecanone, Phytone Phenols para-Ethyltoluene meta-Ethyltoluene Mesitylene Pseudocumene Ester Benzyl cinnamate, Methyl nonanoate Ether 1,8-Cineole

    [0283] Although specific embodiments of the invention have been disclosed, those having ordinary skill in the art will understand that changes can be made to the specific embodiments without departing from the spirit and scope of the invention. The scope of the invention is not to be restricted, therefore, to the specific embodiments disclosed.

    [0284] Insofar as the description above discloses any additional subject matter that is not within the scope of the claims below, the inventions are not dedicated to the public and the right to file one or more applications to claim such additional inventions is reserved.