Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS20090226549 A1
Publication typeApplication
Application numberUS 12/399,295
Publication date10 Sep 2009
Filing date6 Mar 2009
Priority date6 Mar 2008
Also published asWO2009111685A1
Publication number12399295, 399295, US 2009/0226549 A1, US 2009/226549 A1, US 20090226549 A1, US 20090226549A1, US 2009226549 A1, US 2009226549A1, US-A1-20090226549, US-A1-2009226549, US2009/0226549A1, US2009/226549A1, US20090226549 A1, US20090226549A1, US2009226549 A1, US2009226549A1
InventorsKenneth John Hughes, Sylvia Gaysinsky, Roger Michael Browning
Original AssigneeKenneth John Hughes, Sylvia Gaysinsky, Roger Michael Browning
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Herbal extracts and flavor systems for oral products and methods of making the same
US 20090226549 A1
Abstract
The invention provides a method for preparing an herbal extract and a flavor system comprising an herbal extract produced by the process. The invention also provides a flavor system comprising an herbal extract comprising thymol, eugenol, carvacrol and eucalyptol. The invention further provides a flavor system comprising a thyme extract having a minimum inhibitory concentration of less than about 3%. Additionally, the invention provides an oral product comprising a flavor system.
Images(5)
Previous page
Next page
Claims(33)
1. A method for preparing an herbal extract comprising:
a) treating an herb with a low temperature liquid CO2 extraction in the presence of an alcohol to produce an alcohol-herbal extract;
b) distilling the alcohol-herbal extract under vacuum to remove at least a portion of the alcohol and produce a first herbal extract; and
c) molecularly distilling the first herbal extract to produce a second herbal extract.
2. The method of claim 1, wherein the alcohol comprises ethanol.
3. The method of claim 1, wherein the herb is selected from the group consisting of thyme, oregano, clove, cilantro, cinnamon, ginger, lavender, allspice, basil, bay celery seed, pimento, lemongrass, parsley, onion, mustard, tarragon, sage, rosemary, coriander, marjoram, cumin, fennel, and black peppercorn.
4. The method of claim 1, wherein the low temperature is a temperature of less than about 25° C.
5. The method of claim 1, wherein the low temperature is a temperature of about 0° C. to about 10° C.
6. The method of claim 1, wherein the extract has a minimum inhibitory concentration for at least one of Porphyromonas gingivalis, Actinomycess viscosus, Actinomyces naeslundii, Streptococcus mutans, and Fusobacterium nucleatum, and the minimum inhibitory concentration is less than about 2%.
7. The method of claim 6, wherein the extract has a minimum inhibitory concentration of less than about 1%.
8. The method of claim 6, wherein the extract has a minimum inhibitory concentration of less than about 0.5%.
9. The method of claim 1, wherein step (b) is performed at a temperature of about 30° C. and about 50° C.
10. A flavor system comprising an herbal extract produced according to claim 1.
11. A flavor system comprising an herbal extract comprising thymol, eugenol, carvacrol and eucalyptol.
12. The flavor system of claim 11, wherein the herbal extract comprises about 1 to about 60 wt % thymol.
13. The flavor system of claim 11, wherein the herbal extract comprises about 0.01 to about 5 wt % eugenol.
14. The flavor system of claim 11, wherein the herbal extract comprises about 0.1 to about 10 wt % carvacrol.
15. The flavor system of claim 11, wherein the flavor system comprises about 1 to about 12 wt % herbal extract.
16. The flavor system of claim 11, wherein the flavor system comprises about 1 to about 12 wt % herbal extract, and the herbal extract comprises about 1 to about 60 wt % thymol, about 0.01 to about 5 wt % eugenol, and about 0.1 to about 10 wt % carvacrol.
17. The flavor system of claim 11, further comprising at least one characterizing flavor component.
18. The flavor system of claim 17, wherein the at least one characterizing flavor component is selected from the group consisting of flavor oils, menthol crystals, citrus oils, fruit essences, cinnamon, anise, and artificial flavoring agents.
19. The flavor system of claim 17, wherein the at least one characterizing flavor component is a flavor oil, and the flavor oil is selected from the group consisting of peppermint oil, spearmint oil, oil of wintergreen, lavender oil, rosemary oil, clove oil, cinnamon oil and combinations thereof.
20. The flavor system of claim 11, further comprising at least one additional antimicrobial agent.
21. The flavor system of claim 11, wherein the system has a minimum inhibitory concentration for at least one of Porphyromonas gingivalis, Actinomycess viscosus, Actinomyces naeslundii, Streptococcus mutans, and Fusobacterium nucleatum, and the minimum inhibitory concentration is less than about 3%.
22. The flavor system of claim 21, wherein the minimum inhibitory concentration is less than about 2%.
23. The flavor system of claim 21, wherein the minimum inhibitory concentration is less than about 1%.
24. A flavor system comprising a thyme extract having a minimum inhibitory concentration for at least one of Porphyromonas gingivalis, Actinomycess viscosus, Actinomyces naeslundii, Streptococcus mutans, and Fusobacterium nucleatum, and the minimum inhibitory concentration is less than about 3%.
25. The flavor system of claim 24, wherein the minimum inhibitory concentration is less than about 2%.
26. The flavor system of claim 24, wherein the minimum inhibitory concentration is less than about 1%.
27. The flavor system of claim 24, wherein the minimum inhibitory concentration is less than about 0.1%.
28. An oral product comprising the flavor system of claim 10.
29. The oral product of claim 29, wherein the oral product is toothpaste, gum, or lozenges.
30. An oral product comprising the flavor system of claim 11.
31. The oral product of claim 30, wherein the oral product is toothpaste, gum, or lozenges.
32. An oral product comprising the flavor system of claim 24.
33. The oral product of claim 32, wherein the oral product is toothpaste, gum, or lozenges.
Description
    CROSS-REFERENCE TO RELATED APPLICATIONS
  • [0001]
    This application claims the benefit of U.S. Provisional Application No. 61/034,455, filed Mar. 6, 2008, and U.S. Provisional Application No. 61/034,908 filed Mar. 7, 2008, and U.S. Provisional Application No. 61/034,902, filed Mar. 7, 2008 and U.S. Provisional Application No. 61/073,640, filed Jun. 18, 2008; all of which are incorporated by reference herein.
  • BACKGROUND
  • [0002]
    Over the years, many oral products have been developed to include additional ingredients that promote oral hygiene, such as tartar control agents or antibacterial agents, although each of these ingredients brings an added benefit they also cause negative aesthetics, particularly taste. There is still a need for products with improved aesthetics and taste. The present invention provides a method of producing an herbal extract and also a flavor system that can provide both antimicrobial benefits with pleasant organoleptic properties for use in oral products.
  • SUMMARY
  • [0003]
    In one aspect, the invention provides a method for preparing an herbal extract including (1) treating an herb with a low temperature liquid CO2 extraction in the presence of an alcohol to produce an alcohol-herb extract; (2) distilling the alcohol-herb extract to remove at least a portion of the alcohol and produce a first herbal extract; and (3) molecularly distilling the first herbal extract to produce a second herbal extract.
  • [0004]
    In one aspect, the invention provides a flavor system including an herbal extract produced by the above process.
  • [0005]
    In yet another aspect, the invention provides a flavor system including an herbal extract comprising thymol, eugenol, carvacrol and eucalyptol.
  • [0006]
    In a further aspect, the invention provides a flavor system comprising a thyme extract having a minimum inhibitory concentration for at least one of Porphyromonas gingivalis, Actinomycess viscosus, Actinomyces naeslundii, Streptococcus mutans, and Fusobacterium nucleatum, and the minimum inhibitory concentration is less than about 3%.
  • [0007]
    In another aspect, the invention provides an oral product comprising one of the flavor systems of the present invention.
  • BRIEF DESCRIPTION OF DRAWINGS
  • [0008]
    FIG. 1 is a schematic diagram of a system to extract an herbal extract, including treating an herb to a low temperature liquid CO2 extraction process in the presence of ethanol.
  • [0009]
    FIG. 2 is a schematic diagram of a liquid CO2-alcohol extraction process.
  • [0010]
    FIG. 3 is a schematic diagram of a process to remove alcohol from an alcohol-herbal extract resulting from a liquid CO2-alcohol extraction process, using low vacuum distillation.
  • [0011]
    FIG. 4 is a schematic diagram of a molecular distillation process to produce a final herbal extract that is a concentrated distillate.
  • [0012]
    FIG. 5 is a graph of percent release of Marker 1, thymol, and Marker 2, menthol, from chewing gum versus time, to monitor flavor release.
  • DETAILED DESCRIPTION
  • [0013]
    Before any embodiments of the invention are explained in detail, it is to be understood that the invention is not limited in its application to the details of construction and the arrangement of components set forth in the following description or illustrated in the following drawings. The invention is capable of other embodiments and of being practiced or of being carried out in various ways. Also, it is to be understood that the phraseology and terminology used herein is for the purpose of description and should not be regarded as limiting. The use of “including,” “comprising,” or “having” and variations thereof herein is meant to encompass the items listed thereafter and equivalents thereof as well as additional items.
  • [0014]
    It also is understood that any numerical range recited herein includes all values from the lower value to the upper value. For example, if a concentration range is stated as 1% to 50%, it is intended that values such as 2% to 40%, 10% to 30%, or 1% to 3%, etc., are expressly enumerated in this specification. These are only examples of what is specifically intended, and all possible combinations of numerical values between and including the lowest value and the highest value enumerated are to be considered to be expressly stated in this application.
  • [0015]
    The invention provides a process of making an herbal extract. The herbal extract may be derived from thyme, oregano, cilantro, ginger, lavender, allspice, basil, bay, celery seed, pimento, lemongrass, parsley, onion, mustard, tarragon, sage, rosemary, coriander, marjoram, cumin, fennel, cinnamon, clove, black peppercorn and the like. One particularly suitable herbal extract comprises thyme. The herbal extract comprises a mixture of compounds, both active and inactive in providing antimicrobial efficacy and flavor. In a suitable embodiment, the invention provides a process that produces a thyme extract with unique flavoring, coloring, and antimicrobial properties. The process generally includes the following: 1) a first low temperature liquid CO2-alcohol extraction process; 2) a low vacuum distillation process; and 3) a molecular distillation process. The combination of these steps provides a highly concentrated, low color, high flavor and antimicrobial activity herbal extract.
  • [0016]
    The invention also provides a flavor system for the addition to compositions of oral products such as toothpaste, mouth rinse, gums, lozenges, and the like. The flavor system comprises an herbal extract. The flavor system may also include at least one characterizing flavor component, such as a flavor oil. The flavor system may include a second characterizing flavor component, such as menthol crystals. One suitable embodiment of the flavor system comprises thyme extract, peppermint oil and menthol crystals. The compositions are suitably non-toxic and have antimicrobial activity.
  • [0017]
    In another aspect, the invention provides a flavor system that provides antimicrobial activity, wherein the antimicrobial activity is measured by a minimum inhibitory concentration. The flavor system comprises an herbal extract, and has a minimum inhibitory concentration that is less than about 3%, less than about 2%, less than about 1%, less than about 0.5%, less than about 0.3%, less than about 0.2%, less than about 0.1%, less than about 0.05% for at least one of Porphyromonas gingivalis, Actinomyces viscosus, Actinomycess naeslundii, Streptococcus mutans, and Fusobacterium nucleatum.
  • [0018]
    In yet another aspect, the invention provides an oral composition having antimicrobial activity, the oral composition comprising a flavor system including an herbal extract and at least one characterizing flavor component.
  • [0019]
    In one aspect, the invention provides a method for producing an herbal extract. The method comprises 1) extracting an alcohol-herbal extract from the herb using a liquid CO2-alcohol extraction at temperatures less than about 25° C.; 2) distilling the alcohol-herbal extract under vacuum to remove at least a portion of the alcohol and produce a first herbal extract; and 3) molecularly distilling the first herbal extract to produce a second herbal extract.
  • [0020]
    The first step includes treating the herb to a low temperature liquid CO2 extraction process in the presence of ethanol. This process is illustrated in FIG. 1 and FIG. 2.
  • [0021]
    Dry herbs (1) are milled on a hammermill with an about 1 millimeter to about 7 millimeter screen to increase the surface area and rupture the herb. The herb is blended with at least about 10%, at least about 15%, at least about 20%, at least about 25%, or at least about 30% of its own weight of de-ionized water, using a ribbon mixer or similar equipment until homogenous, e.g., about 5 minutes. The dampened herb material (1) is packed into a series of extraction columns (20). The columns are treated by dynamic flow of liquid carbon dioxide (10) injected with alcohol (11) as a co-extraction entrainer. In a suitable embodiment, the amount of CO2-alcohol used can be measured as a mean flow rate through the extraction column. Suitable flow rates include at least about 150 kg/hr, at least about 175 kg/hr, at least about 200 kg/hr, at least about 222 kg/hr, or at least about 240 kg/hr. The flow rate may be less than about 350 kg/hr, less than about 325 kg/hr, less than about 300 kg/hr, less than about 275 kg/hr, or less than about 260 kg/hr.
  • [0022]
    The ratio of CO2 to alcohol may vary according to the herb being processed. In a suitable embodiment, the alcohol is provided in at least about 0.1%, at least about 0.2%, at least about 0.3%, at least about 0.5%, at least about 0.7%, at least about 1.0%, or at least about 2.0% by weight in the liquid CO2. In a suitable embodiment, the alcohol is provided at a mean flow rate of 1 kg/hr with the CO2 provided at a mean flow rate of 250 kg/hr. In one embodiment, the alcohol is ethanol.
  • [0023]
    The CO2-alcohol is provided to the extraction columns under pressure, the pressure being at least about 35 atmosphere, at least about 40 atmosphere, at least about 45 atmosphere, at least about 50 atmosphere, at least about 55 atmosphere, or at least about 60 atmosphere, wherein a suitable range is about 45-55 atmosphere. The process is driven by an approximately 10 atmosphere differential within the plant during operation.
  • [0024]
    In certain embodiments, this process is carried out at temperatures that are less than about 25° C., less than about 20° C., less than about 15° C., less than about 12° C. Suitably the temperature may be between about 0° C. and about 10° C. In a suitable embodiment, the temperature is about 7° C.±1° C. These temperatures are below the temperatures used in supercritical CO2 extraction which occur above the critical temperature 31° C., and more typically at 40-60° C., and very often higher. The lower temperatures concentrate more of the volatile components in the extract and avoid the decomposition of components. The liquid CO2 phase extraction is more selective for more volatile components and therefore achieves higher concentrations of them.
  • [0025]
    The liquefied carbon dioxide-alcohol is a unique solvent mixture that dissolves the low molecular weight organoleptically active components of the herb. The low temperature and pressurized system prevents the degradation and loss of volatiles which may typically occur with a traditional essential oil distillation process, while higher molecular weight unwanted materials such as heavier fats, waxes, pigments, sugars, starches and tannins are excluded by this extraction process. The CO2-alcohol-herb extract solution emerging from the extraction columns is passed to a heat exchanger (21) where the temperature is raised a few degrees within the closed system, and the CO2 is changed to vapor by the change in temperature and removed via pipe work to the compressor for recycling to liquid CO2 through the process. The alcohol-extract is collected from the system as a cold foam product, and as the foam warms to room temperature any residual CO2 vaporizes and leaves the alcohol-herbal extract (2). The time of extraction depends on the material used and can be readily determined by one of ordinary skill in the art. For a thyme extract, the extraction time per extraction column filled with thyme leaves (about at least 25 kg, more suitably 28 kg) is at least about 4 hours.
  • [0026]
    FIG. 2 charts a description of the CO2-alcohol extraction process in detail. Liquid CO2 1 enters the system into a liquid CO2 holding tank 2. The CO2 is processed through a heat exchanger 3 and a refrigeration unit 4 to provide the liquid CO2 at the desired temperature of about 7° C. The liquid CO2 is injected with alcohol from an alcohol storage tank 6 via a co-entainer pump 7. The liquid CO2-alcohol solvent is pumped through a set of extraction columns 8A-E which hold the milled herbal leaves. The liquid CO2-alcohol -herbal extract is processed through the heat exchanger 3 (giving an initial input of energy into the extract) to an automatic mixing valve 9, an automatic flow control valve 10 and filters 11 into a main condenser-heat exchanger 12 where the CO2 is recycled back into the CO2 holding tank 2 and the product is collected via the product collection pump 17 to a product tap 18. CO2 is also purified to be reused and recovered from the condenser-heat exchanger 12 through a demisting filter 13, a compressor 14, a de-oil misting filter 15 and at a vapor temperature control 16. A vaporizer 19 pumps warm vapor back into the extraction columns 8.
  • [0027]
    A second step of the process includes processing the alcohol-herbal extract from the extraction through a low vacuum distillation process to remove the alcohol as depicted in FIG. 3 and form a first herbal extract (3). This process can be carried out using a suitable vacuum still (23). The alcohol is removed under low vacuum distillation at typically a temperature of at least about 20° C., at least about 30° C., at least about 35° C., at least about 40° C., at least about 45° C., at least about 50° C., at least about 55° C., or at least about 60° C., one suitable range is between about 30 to about 40° C., finishing at a maximum of about at least 60° C., to reduce the alcohol content to a residual level. Residual alcohol may be less than about 25%, less than about 20%, less than about 15%, or less than about 10%. The residual alcohol may be at least about 0.05%, at least about 0.1%, at least about 0.2%, at least about 0.5%, at least about 1%, at least about 2%, or at least about 5%.
  • [0028]
    A third step of the process includes a molecular distillation process. A falling-film short path still may be used. Suitable stills such as models KD5 or KD10 Molecular Stills are available from UIC GmbH of Germany. This step of the process is depicted in FIG. 4. This special design of the still subjects the material being processed to heating for the briefest possible time while allowing a very high vacuum to be achieved, lowering the vaporizing temperature and thus greatly limiting the overall exposure of the extract. Suitably, the liquid extract (3) is continuously feed into the still (40) and passes down the inside of a heated jacket (28), which is at about at least 80° C., at least about 90° C., or at least about 100° C., as a thin film produced by the centrifugal force of the rotating rollers (27), and falls by gravity to be collected. This process is carried out under high vacuum conditions, wherein the pressure is suitably at least about 5×10−4 mbar, at least about 1×10−3 mbar, at least about 1.5×10−3 mbar, or at least about 2×10−3 mbar. The pressure is suitably at least less than about 1×10−2 mbar, less than about 5×10−2 mbar, less than about 7×10−2 mbar, or less than about 1×10−3. The extract is subjected to heat typically for only a few minutes. Suitably, the extract passes through the system at a rate of about at least 1 kg/hr, at least about 2 kg/hr, at least about 3 kg/hr, at least about 5 kg/hr, at least about 7 kg/hr, at least about 8 kg/hr, or at least about 10 kg/hr. In a suitable embodiment, the rate is about 1 to about 2 kg/hr for a KD10 Molecular Still. The volatile material passes as a laminar flow of vapor across a very short path onto a condenser (30) which is concentric at the center of the roller assembly, and falls by gravity into a receiver. This laminar flow, coupled with the use of high efficiency rotary and oil diffusion vacuum pumps and a liquid nitrogen trap at −200° C. allows vacuum pressures down to 10−6 atmosphere to be achieved. Materials in the extract that would be damaged or even decomposed during traditional distillation are separated and purified into the final herbal extract. This process produces a second herbal extract (4) that is a concentrated distillate with reduced color.
  • [0029]
    As mentioned above, the invention also provides a flavor system comprising the herbal extract. The herbal extract is suitably provided as at least about 1% wt/wt, at least about 2% wt/wt, at least about 4% wt/wt, at least about 6% wt/wt, at least about 9% wt/wt, at least about 15% wt/wt, at least about 20% wt/wt, or at least about 25% wt/wt of the flavor system. The thyme extract is suitably provided as less than about 30% wt/wt, less than about 20% wt/wt, less than about 15% wt/wt, less than about 12% wt/wt of the flavor system.
  • [0030]
    One suitable herbal extract is a thyme extract derived from dry thyme by the process described above. The thyme extract is a mixture of compounds, both active and inactive in providing antimicrobial efficacy and flavor. Suitable processes produce thyme extract with unique flavoring and antimicrobial properties. This thyme extract has unique and beneficial properties from thyme oils produced by other known methods. The main active ingredients of the thyme extract that provide antimicrobial efficacy include thymol, eugenol, carvacrol and eucalyptol. Thyme extract also includes a number of inactive ingredients, some of which can be found in Table 7. The unique chemical composition of this extract provides the unique flavor, color and antimicrobial properties. The thyme extract provides a more appealing flavor in addition to antimicrobial benefits. One example of a suitable thyme extract is THYME TEMPLAR™ available from Sensient Flavors, Inc. (Indianapolis, Ind.).
  • [0031]
    The flavor system may also include at least one characterizing flavor component that provides organoleptic properties of pleasant taste and smell, and may provide additional antimicrobial activity as well. A first characterizing flavor component may constitute suitably at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 47%, at least about 50%, at least about 60%, or at least about 70% wt/wt of the flavor system. The first characterizing flavor component may constitute less than about 70% wt/wt, less than about 60% wt/wt, less than about 55% wt/wt, less than about 50% wt/wt, less than about 40% wt/wt, or less than about 20% wt/wt of the flavor system. The first characterizing flavor component may be a flavor oil. Examples of flavor oils that may be used include, but are not limited to, peppermint oil, spearmint oil, oil of wintergreen, lavender oil, rosemary oil, clove oil and cinnamon oil.
  • [0032]
    The flavor system may also include a second characterizing flavor component. The flavor system may suitably includes at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50% wt/wt, at least about 60% wt/wt, or at least about 70% wt/wt of the secondary flavor component. The flavor system may suitably include less than about 70%, less than about 60%, less than about 50%, less than about 40%, less than about 30%, less than about 20%, less than about 15%, or less than about 10% of the secondary flavor component. One example of a secondary flavor component includes, but is not limited to, menthol crystals, C10H20O, which are an organic compound made synthetically or obtained from mint oils, most commonly produced from Mentha arvensis. Menthol is a waxy, clear or white crystalline substance commercially available from Monarchy Aromatics, Ltd.
  • [0033]
    Additional examples of first and second characterizing flavor components may be from oils, crystals, liquid concentrates, synthetic flavors, or combinations thereof. Additional characterizing flavor components may include, but are not limited to, oils derived from plants and fruit such as citrus oils, fruit essences, peppermint oil, spearmint oil, other mint oils, clove oil, oil of wintergreen, cinnamon, anise, artificial flavoring agents such aldehyde flavors including, but are not limited to, acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, i.e., alpha citral (lemon, lime), neral, i.e., beta citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotropine, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde (spicy fruity flavors), citronellal (modifies, many types), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits), 2-ethyl butyraldehyde (berry fruits), hexenal, i.e., trans-2 (berry fruits), tolyl aldehyde (cherry, almond), veratraldehyde (vanilla), 2,6-dimethyl-5-heptenal, i.e., Melonal (melon), 2,6-dimethyloctanal (green fruit), and, 2-dodecenal (citrus, mandarin). Those skilled in the art will recognize that natural and artificial secondary flavor components may be combined in any sensorally acceptable fashion. All such flavors and flavor blends are contemplated by the present invention.
  • [0034]
    As mentioned above, the invention also provides a flavor system comprising an herbal extract. “Antimicrobial activity,” as described herein, is the ability of an herbal extract to retard the growth of and/or prevent the growth of oral bacteria. Examples of representative gram-positive and gram-negative oral bacteria include, but are not limited to, Actinmoyces viscosus Actinomyces naeslundii, Fusobacteriumm nucleatum, Porphyromonas gingivalis, Streptococcus mutans, and Streptococcus sanguis. Anti-microbial activity can be measured by the minimum inhibitory concentration of the agent. The minimum inhibitory concentration of an herbal extract is the concentration of the extract within a test sample at which no bacterial growth is observed. The test sample may be saliva or a suitable bacterial culture. In the examples below, the minimum inhibitory concentration is provided as a percentage.
  • [0035]
    The minimum inhibitory concentration for the herbal extract is measured as a percent volume (e.g., 1% would be one part flavor system in 99 parts test sample) as described in the example below. The herbal extract may provide antimicrobial activity as measured by minimum inhibitory concentration (MIC) of at least about 0.01%, at least about 0.05%, at least about 0.1%, at least about 0.2%, at least about 0.5% for an oral bacteria. The herbal extract may provide antimicrobial activity as measured by minimum inhibitory concentration of less than about 5%, less than about 3%, less than about 2%, less than about 1%, less than about 0.5%, less than about 0.3%, less than about 0.2%, less than about 0.1% for an oral bacterial.
  • [0036]
    The flavor system may include additional antimicrobial agents. Suitable antimicrobial agents include, but are not limited to, cedarwood oil, chloramphenicol, berberine, Glycyrrhiza glabra extract, juicy fruit basil oil, juniper berries oil, lemon basil oil, orally active metallic ion such as salts of zinc, tin, silver and copper, hexylresorcinol, cetylpyridinium chloride, chlorhexidine digluconate, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, commonly referred to as triclosan, phthalic acid and its salts including, but not limited to those disclosed in U.S. Pat. No. 4,994,262, substituted monoperthalic acid and its salts and esters as disclosed in U.S. Pat. Nos. 4,990,329, 5,110,583, and 4,716,035, magnesium monoperoxy phthalate, chlorhexidine (Merck Index, no. 2090), alexidine (Merck Index, no. 222, hexetidine (Merck Index, no. 4624), sanguinarine (Merck Index, no. 8320), benzalkonium chloride (Merck Index, no. 1066), salicylanilide (Merck Index, no. 8299), domiphen bromide (Merck Index, no. 3411), cetylpyridinium chloride (CPC) (Merck Index no. 2024, tetradecylpyridinium chloride (TPC), N-tetradecyl-4-ethyllpyridinium chloride (TDEPC), octenidine, delmopinol, octapinol, and other piperidino derivatives, niacin preparations, zinc/stannous ion agents, antibiotics such as augmentin, amoxicillin, tetracycline, doxycycline, minocycline, and metronidazole; and analogs and salts of the above; essential oils including thymol, geraniol, carvacrol, citral, hinokitiol, eucalyptol, catechol (particularly 4-allyl catechol) and mixtures thereof; methyl salicylate; hydrogen peroxide; metal salts of chlorite and mixtures of all of the above. Each of the patents recited herein are hereby fully incorporated by reference.
  • [0037]
    Sweeteners may also be included in the flavor system. Suitable sugar sweeteners include, but are not limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, glucose, galactose, corn syrup solids, stevioside, Lo-Han Guo, and the like, alone or in combination. Sugarless sweeteners include, but are not limited to, sugar alcohols such as sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitose, and the like, alone or in combination. High intensity artificial sweeteners can also be used alone or in combination with other sweeteners. These sweeteners include, but are not limited to, sucralose, aspartame, MAPM derivatives such as neotame, salts of acesulfame, altitame, saccharin and its salts, cyclamic acid and its salts, glycyrrhizinate, dihydrochalcones, thaumatin, monellin, and the like, alone or in combination.
  • [0038]
    In one embodiment, the flavor systems are manufactured by mixing a first characterizing flavor component (e.g., peppermint oil) with a second characterizing flavor component (e.g., menthol crystals) and heating the mixture to at least about 35° C., to at least about 40° C., to at least about 45° C., to at least about 50° C., to at least about 55° C., to at least about 60° C., to at least about 65° C. until the second characterizing flavor component is melted in a standard mixer. The mixture is mixed until homogenous and then cooled. The thyme extract is added to the mixture and mixed until homogenous. In another embodiment, the thyme extract may be added to a first characterizing flavor component without the use of a second flavoring component and mixed until homogenous. The thyme extract and first characterizing flavor component may be mixed at room temperature. Other flavors may also be added and mixed until homogenous.
  • [0039]
    The flavor systems may be used in the preparation of spray dried flavor compositions. The flavor systems may be combined with encapsulating agents such as the starch-based encapsulating agent Hi-Cap 100 from National Starch (Bridgewater, N.J., U.S.A.) and water. Other suitable encapsulating agents may include N-Lok® 1930, CAPSUL®, CAPSUL®TA (all from National Starch), and EmCap™ (from Cargill, Inc., Cedar Rapids, Iowa, U.S.A.). The water and starch-based encapsulating agent may be mixed, and a flavor system may be added to the starch and water mixture to form an emulsion. The emulsion may be dried with an inlet temperature of about 160° C. The encapsulating agent may be present in amounts of at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, or at least about 50% by weight of the total spray dried flavor composition. The encapsulating agent may be present in a suitable amount less than about 50%, less than about 40%, less than about 20%, less than about 10%, or less than about 5% by weight of spray dried flavor composition. The flavor system may be added to amounts of at least about 0.5%, at least about 0.8%, at least about 1%, at least about 2%, at least about 4%, at least about 6%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, or at least about 70% by weight of the total spray dried flavor composition. The flavor system may be used in the composition in a suitable amount less than about 60%, less than about 50%, less than about 20%, less than about 12%, less than about 10%, less than about 7%, less than about 5%, less than about 3%, or less than about 2% by weight of spray dried flavor composition. The spray dried flavor formulations may be used with or without other flavor systems and may be incorporated into compositions such as water, chewing gums, toothpaste, mouth rinse, liquid dentifrice, lozenges, liquid spray, and edible films.
  • [0040]
    The flavor systems may be used in the preparation of oral compositions for oral products by the addition of the flavor system at amounts of at least about 0.5%, at least about 0.8%, at least about 1%, at least about 2%, at least about 4%, at least about 6%, at least about 10% by weight of the total oral composition. The flavor system may be used in the oral composition in a suitable amount less than about 20%, less than about 12%, less than about 10%, less than about 7%, less than about 5%, less than about 3%, less than about 2% by weight of the oral composition. Oral compositions may be products which in the ordinary course of usage are not intentionally swallowed for purposes of systemic administration of particular therapeutics agents, but are rather retained in the oral cavity for a time sufficient to contact substantially all the dental surfaces and/or oral tissues for purposes of oral activity. Methods of preparing the oral compositions may include mixing the flavor system by conventional methods to an oral delivery agent. Oral delivery agents include, but are not limited to, a toothpaste, mouth rinse, liquid dentifrice, gum, lozenges, liquid spray, and edible films. Toothpaste may be paste or gel formulations unless otherwise specified. The amount of flavor system added depends on the particular oral composition to which it is added. For example, chewing gums may include at least about 0.5%, more suitably at least about 2% wt/wt of flavor system while edible oral films may comprise at least about 6%, more suitable at least about 10% wt/wt of the flavor system due to their very low weight. The oral compositions comprise a sufficient amount of the flavor system to provide antimicrobial activity.
  • [0041]
    The oral compositions may include sweeteners as described above. Further, the oral compositions may include other antimicrobial agents. The oral compositions may also contain other flavoring agents, if desired. The flavoring agents may include essential oils, synthetic flavors or mixtures thereof including, but not limited to, oils derived from plants and fruits, such as citrus oils, fruit essences, peppermint oil, spearmint oil, other mint oils, clove oil, oil of wintergreen, anise and the like. Artificial flavoring agents and components may also be used. Natural and artificial flavoring agents may be combined in any sensorially acceptable fashion. Flavoring may include a cooling agent to enhance the flavor and perceived freshness.
  • [0042]
    The oral compositions may be chewing gums or any variation including but not limited to bubble gums, pellets, gum balls or sticks. Chewing gums may be coated or not coated and be of a variety of flavors, shapes and sizes. A chewing gum composition includes a gum base, and a suitable amount of the flavor system as described above. Chewing gum may be manufactured by any suitable conventional method. The base for the chewing gum includes an elastomer of a type normally employed in chewing gums, e.g., chicle, gum, jelutong, balata, crown gum, gutta-percha, sorva, butadiene-styrene copolymer, polyisobutylene, isobutylene-isoprene copolymer, polyethylene, and the like or mixtures thereof. Softeners may be added to chewing gum in order to optimize the chewability and mouth-feel of the gum. Chewing gums may include at least about 0.1%, at least about 0.5%, at least about 1%, at least about 2% of the flavor system. Chewing gums may include less than about 3%, less than about 2.5%, less than about 2% of the flavor system.
  • [0043]
    The following examples further describe and demonstrate embodiments within the scope of the present invention. These examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention as many variations thereof are possible without departing from the spirit and scope.
  • EXAMPLES
  • [0044]
    All percentages described in the following examples are percent weight unless indicated otherwise.
  • Example 1
  • [0045]
    Dry thyme leaves were milled on a hammermill with a 3 millimeter screen to increase the surface area and rupture the leaves. 28 kg of dry milled thyme leaves were added to 8.4 kg of water and mixed in a ribbon mixer until homogenous, about 5 minutes. The moistened thyme leaves were added to a stainless steel extraction column. Each extraction column was loaded with 28 kg dry thyme leaves. Three extraction columns were used. Liquid CO2 was injected with 1 kg/hr of ethanol (96A % natural fermentation grade), the CO2 provided to the extractor at a rate of 250 kg/hr for 4 hours per extraction column under 45 atmosphere pressure at 7° C.±1°. The CO2-ethanol-thyme extract was collected and passed through a heat exchanger which vaporizes the CO2 to produce an ethanol-thyme extract to yield about 17% the weight of the initial leaves at this stage. The ethanol-thyme extract was processed by low vacuum distillation at 35° C. at 200 mbar to remove the ethanol in a batch still. The distilled thyme-extract was then treated on a thin-film molecular distillation unit (KD5 model, UIC GmbH of Germany) under vacuum pressure of 10−6 atmospheres at 100° C. at a flow rate of 1 kg per hour. The thyme extract was analyzed by mass spectroscopy and an exemplary list of the chemical composition of the thyme extract is shown in Table 1.
  • [0000]
    TABLE 1
    Thyme extract
    Compound %
    Ethanol 5.03
    Acetic Acid 0.349
    1-octen-3-ol 1.031
    p-cymene 6.382
    Eucalyptol 0.43
    Linalool 2.354
    Camphor 0.232
    Boreol 1.423
    4-terpineol 0.542
    thymol methyl ether 0.701
    carvacrol methyl ether 1.141
    Thymol 58.468
    Carvacrol 4.436
    Eugenol 0.589
    beta-caryophyllene 1.326
    caryophyllene oxide 0.794
    Total 85.228
  • Example 2
  • [0046]
    A flavor system was formulated using the components set forth in Table 2.
  • [0000]
    TABLE 2
    % material
    % material in final
    Flavor B in formula flavor system
    Thyme extract (THYME TEMPLAR ™,   1-50% 1-12%
    Sensient Flavors, Indianapolis, IN) 0.01-5%
    Primarily composed of: 0.1-10%
    Thymol
    Eugenol
    Carvacrol
    Eucalyptol
    Menthol crystals 15-50%
    (Monarchy Aromatics, Ltd,)
    Peppermint oil 25-60%
    (F. D. Copeland and Sons, Ltd)
    Natural Thymol 0.1-0.8%
    TOTAL 100%
  • [0047]
    The peppermint oil and menthol crystals were added together in a standard mixer and heated to 113° F. and mixed until homogenous. The mixture was then cooled and the thyme extract and natural thymol were added and mixed until homogenous.
  • Example 3
  • [0048]
    A flavor system formulation was prepared using the following formulation in Table 3.
  • [0000]
    TABLE 3
    % material
    % material in final
    Flavor C in formula flavor system
    Thyme extract (THYME TEMPLAR ™, 50%  5%
    Sensient Flavors, Indianapolis, IN)  7% (2.5-3%)
    Primarily composed of:
    Thymol
    Eugenol
    Carvacrol
    Eucalyptol
    Menthol crystals 40%
    (Monarchy Aromatics, Ltd,)
    Peppermint oil 55%
    (F. D. Copeland and Sons, Ltd)
    TOTAL 100% 
  • [0049]
    The peppermint oil and menthol crystals were added together in a standard mixer, heated to 113° F. until the menthol crystals dissolved, and the mixture was cooled. The thyme extract was then added to the mixture and mixed until homogeneous.
  • [0050]
    A batch of flavor system formulation C was analyzed by gas chromatography/mass spectrometry (GC/MS) using standard methods providing the main chemical composition of formulation C as shown in Table 4.
  • [0000]
    TABLE 4
    Flavor C composition
    Compound %
    b-cymene 0.376
    Eucalypto + Limonene 2.892
    Menthone 13.125
    Isomenthone 2.798
    Menthofuran 1.609
    Neomenthol 2.317
    Menthol 63.53
    Pulegone 1.059
    Thymol 2.506
    Methyl Acetate 2.578
    Beta-caryophyllene 1.038
    Germacrene 0.416
    Other ingredients 5.8
    Total 100
  • Example 4
  • [0051]
    A flavor system formulation was prepared as described in Example 3 but using the following formulation in Table 5.
  • [0000]
    TABLE 5
    % material
    % material in final
    Flavor D in formula flavor system
    Thyme Templar (THYME TEMPLAR ™, 50%  9%
    Sensient Flavors, Indianapolis, IN)  7% (2.5-3%)
    Primarily composed of:
    Thymol
    Eugenol
    Carvacrol
    Eucalyptol
    Menthol crystals 38%
    (Monarchy Aromatics, Ltd,)
    Peppermint oil 53%
    (F. D. Copeland and Sons, Ltd)
    TOTAL 100% 
  • [0052]
    A batch of flavor system of formulation D was analyzed as described in Example 3. The formulation of the main chemical compositions of formula D can be found in Table 6.
  • [0000]
    TABLE 6
    Flavor D composition
    Compound %
    b-cymene 0.638
    eucalypto + Limonene 2.623
    Menthone 11.805
    Isomenthone 2.53
    Menthofuran 1.445
    Neomenthol 2.122
    Menthol 62.895
    Pulegone 1
    Thymol 4.963
    Methyl Acetate 2.514
    Beta-caryophyllene 0.97
    Germacrene 0.379
    Other 6.116
    Total 100
  • Example 5 Chewing Gum Containing Flavor Systems
  • [0053]
    Chewing gum compositions are prepared by incorporating the flavor systems of Examples 3 and 4 with a chewing gum (Trident gum manufactured by Cadbury Adams located in Parsippany N.J.). The flavor systems are added at 2% weight of the composition of the gum.
  • Example 6 Liquid Filled Chewing Gum
  • [0054]
    Liquid filled chewing gum compositions, Dentyne Ice (manufactured Cadbury Adams located in Parsippany N.J.), are prepared by incorporating the flavor systems of Examples 3 and 4, the liquid portion of Dentyne Ice gum filling is mixed with 0.1% of the flavor system and the solid portion of the Dentyne Ice gum base is mixed with 3% of the flavor system.
  • Example 7 Liquid Filled Chewing Gum
  • [0055]
    Liquid filled chewing gum compositions, Dentyne Ice (manufactured by Cadbury Adams located in Parsippany N.J.), are prepared by incorporating the flavor systems of Examples 3 and 4, the liquid portion of Dentyne Ice gum filling is mixed with 1.0% of the flavor system and the solid portion of the Dentyne Ice gum base is mixed with 3% of the flavor system.
  • Example 8 Mouth Rinse Containing Flavor System
  • [0056]
    Mouth rinse compositions are prepared by mixing 2% by weight of the flavor systems of Examples 3 and 4 with a mouth rinse.
  • Example 9 Toothpaste Containing Flavor System
  • [0057]
    Toothpaste compositions are prepared by mixing 2% of flavor systems of Examples 3 and 4 with unflavored toothpaste until the mixture is homogenous.
  • Example 10 Edible Film Containing Flavor System
  • [0058]
    Edible film compositions are prepared by mixing 10% by weight of the flavor systems of Examples 3 and 4 with a substance to form an edible film.
  • Example 11 Composition of Thyme Extract
  • [0059]
    The composition of the thyme extract (THYME TEMPLAR™) obtained by ethanol CO2 extraction process was analyzed as described in Example 3. An exemplary list of the chemical composition is shown in Table 7.
  • [0000]
    TABLE 7
    Thyme extract
    Compound %
    Ethanol 5.03
    Acetic Acid 0.349
    1-octen-3-ol 1.031
    p-cymene 6.382
    Eucalyptol 0.43
    Linalool 2.354
    Camphor 0.232
    Boreol 1.423
    4-terpineol 0.542
    thymol methyl ether 0.701
    carvacrol methyl ether 1.141
    Thymol 58.468
    Carvacrol 4.436
    Eugenol 0.589
    beta-caryophyllene 1.326
    caryophyllene oxide 0.794
    Total 85.228
  • Example 12 Antimicrobial Activity of Flavor System
  • [0060]
    In vitro studies were preformed at Indiana University School of Dentistry at the Indiana University-Purdue University of Indianapolis (IUPUI) to test for the antimicrobial activity of the flavor systems. Porphyromonas gingivalis (PG, ATCC 33277), Actinomyces viscosus (AV, ATCC 19246), Actinomycess naeslundii (AN, ATCC 12104), Streptococcus mutans (SM, ATCC 25175), and Fusobacterium nucleatum (FN, ATCC 31647) were used to determine the minimum inhibitory concentration of 4 different flavor systems, A-D. Thyme extract is Flavor A as described in Example 8, and flavor systems B-D are as described in Examples 2-4. The four flavor systems were provided in an undiluted form and each flavor system was diluted to the working test solutions of 1.0%, 0.5%, 0.05%, and 0.001% (v/v) flavor system. Each testing system had a final volume of 2.0 ml, each containing at least 1×106 bacteria, adequate amount of the flavor system to obtain the working test solution, 1 ml of double strength enriched trypticase-soy broth and saline solution to bring the final volume up to 2 ml. Each test was run in triplicate.
  • [0061]
    Each testing sample was vigorously vortexed for 30 to 60 seconds to enhance physical contact of the bacteria with the relatively insoluble test products. A 1.0 ml aliquot was taken and placed into a flask containing 250 ml of Trypticase Soy Broth (TSB) supplemented with 0.25% (w/v) glucose. Flasks containing Porphyromonas gingivalis or Fusobacterium nucleatum were incubated at 37° C. in an anaerobic chamber (85% N2—10% CO2—5% H2), while the other bacteria flasks were incubated at 37° C. in ambient air. Samples were evaluated after 24 hours. The minimal inhibitory concentration (MIC) was determined as the test sample with the greatest dilution that exhibited no bacteria growth (e.g., remained clear, not turbid). MIC scores for each of the flavor systems for each of the bacteria tested are shown in Table 8.
  • [0000]
    TABLE 8
    Flavor FN AN AV PG SM
    A 0.05% 0.05%  0.05%  <0.01%   0.05% 
    B 0.05% 0.1% 0.5% 0.05% 0.5%
    C 0.05% 0.5% 0.1% 0.05% 0.1%
    D  0.1% 0.1% 0.5% 0.05%   1%
  • Example 13 Flavor Release from Chewing Gum
  • [0062]
    To test if adequate flavor is released from chewing gum, the chewing gums made in Example 5 were tested using a mechanical instrument to simulate human mastication of chewing gum, which can be found in Kleber et al. A mastication device designed for the evaluation of chewing gum is set forth in Journal of Dental Research, 1981, 109-114, which is incorporated herein in its entirety. Artificial saliva (15 ml) was placed in the reservoir, and the thermostatically controlled heating element was turned on to maintain the saliva and gum at body temperature for proper chewing consistency. One stick of test chewing gum (approximately 3 grams with 2% flavor system added) was placed in the warmed chamber and the artificial saliva was exposed to the chewing gum for 1 minute under chewing simulation conditions. All the artificial saliva (15 ml) was removed as quickly as possible with a pipette, delivered immediately into a glass bottle and sealed. The saliva was replaced with a fresh 15 ml aliquot, the chewing conditions restarted and the gum samples were treated for another minute. This process was repeated at the appropriate intervals to yield cumulative treatment times of 1, 2, 5, 10, 15, 20 and 30 minutes. The reservoir and mastication devices were thoroughly cleaned and rinsed, and the process repeated with another sample of chewing gum.
  • [0063]
    Two markers, Marker 1, thymol, and Marker 2, menthol, were selected to monitor flavor release based on quantity and antimicrobial efficiency. FIG. 5 shows release of the two markers at different predetermined times. Based on marker release, it was estimated that most of the flavor was released for Marker 2 between 5 and 10 minutes of chewing. Marker 1 was released constantly for the first 10 minutes and afterward decreases. Marker 2 was released at 55% in flavor C and flavor D while 40.8% and 33% of Marker 1 was released from flavor C and D respectively. It was estimated that enough flavor was released during the first 15-20 minutes to have antimicrobial activity based on the quantity released and the MIC results.
  • Example 14
  • [0064]
    Dry thyme leaves were milled on a hammermill with a 3 millimeter screen to increase the surface area and rupture the leaves. 28 kg of dry milled thyme leaves were added to 8.4 kg of water and mixed in a ribbon mixer until homogenous, about 5 minutes. The moistened thyme leaves were added to a stainless steel extraction column. Each extraction column was loaded with 28 kg dry thyme leaves. Three extraction columns were used. Liquid CO2 was injected with 1 kg/hr of ethanol (96A % natural fermentation grade), the CO2 provided to the extractor at a rate of 250 kg/hr for 4 hours per extraction column under 45 atmosphere pressure at 7° C.±1°. The CO2-ethanol-thyme extract was collected and passed through a heat exchanger which vaporizes the CO2 to produce an ethanol-thyme extract to yield about 17% the weight of the initial leaves at this stage. The ethanol-thyme extract was processed by low vacuum distillation at 35° C. at 200 mbar to remove the ethanol in a batch still. The distilled thyme-extract was then treated on a thin-film molecular still (KD5 model, UIC GmbH of Germany) under vacuum pressure of 10−6 atmospheres at 100° C. at a flow rate of 1 kg per hour.
  • Example 15
  • [0065]
    An anti-microbial spray dried flavor formulation was prepared by mixing water and a starch-based encapsulating agent such as Hi-Cap 100 (National Starch, Bridgewater, N.J., U.S.A.). An oil flavor system was prepared as described in Example 3 except with the formulation according to Table 9. The oil flavor system was added to the starch and water to form an emulsion at a concentration of 16% (wt/wt) flavor system, 24% (wt/wt) Hi-Cap 100, and 60% (wt/wt) water with an average particle size of about 0.5 μm. The emulsion was then spray dried with an inlet temperature of about 160° C.
  • [0000]
    TABLE 9
    % material
    % material in final
    Flavor E in formula flavor system
    Thyme Templar (THYME TEMPLAR ™, 50%
    Sensient Flavor, Indianapolis, IN)
    Menthol crystals  0%
    (Monarchy Aromatics, Ltd,)
    Peppermint oil 50%
    (F. D. Copeland and Sons, Ltd)
    TOTAL 100% 
  • [0066]
    The final spray dried formulation was made into a volatile oil composition and analyzed with GC-MS. The chemical composition is shown in Table 10. Encapsulation of the flavor system removed water and some (about 20-60%) of the volatile oils from the formulation, resulting in about 40% load encapsulation.
  • [0000]
    TABLE 10
    Anti-M Spray Dried
    Anti-microbial Compound %
    Carvacrol    1%
    Thymol 12.098%
    Eugenol  0.25%
    Eucalyptol    2%
    Menthol (from peppermint oil)  8.75%
    Other compounds 75.902%
    Total   100%
  • [0067]
    The anti-microbial spray dried flavor formulation may be incorporated into compositions such as water, chewing gums, toothpaste, mouth rinse, liquid dentifrice, lozenges, liquid spray, and edible films.
  • Example 16
  • [0068]
    A breath freshening spray dried flavor formulation was prepared by mixing water and a starch-based encapsulating agent such as Hi-Cap 100 (National Starch, Bridgewater, N.J., U.S.A.). The oil flavor system as prepared and described in Example 3 (5% THYME TEMPLAR™, 40% menthol crystals, 55% peppermint oil) was added to the starch and water mixture to form an emulsion at a concentration of 16% (wt/wt) flavor system, 24% (wt/wt) Hi-Cap 100, and 60% (wt/wt) water with an average particle size of about 0.5 μm. The emulsion was then spray dried with an inlet temperature of about 160° C.
  • [0069]
    The final spray dried formulation was made into a volatile oil composition and analyzed with GC-MS. The chemical composition is shown in Table 11. Encapsulation of the flavor system removed water and some (about 20-60%) of the volatile oils from the formulation, resulting in about 40% load encapsulation.
  • [0000]
    TABLE 11
    Breath Freshening Spray Dried
    Anti-microbial Compound %
    Menthol 22.891%
    Thymol  1.17%
    Eucalyptol   0.5%
    Carvacrol   0.5%
    Other compounds 74.939%
    Total   100%
  • [0070]
    The breath freshening spray dried formulation may be incorporated into compositions such as water, chewing gums, toothpaste, mouth rinse, liquid dentifrice, lozenges, liquid spray, and edible films.
Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3746553 *24 Mar 197117 Jul 1973Kraft Sesame CorpProcess for cleaning spices and herbs
US3821417 *14 Oct 197128 Jun 1974Sahaydak MFlavor preservation in chewing gum compositions and candy products
US3947570 *22 Nov 197430 Mar 1976Colgate-Palmolive CompanyOral product
US4136065 *6 Jun 197723 Jan 1979Asahi Kasei Kogyo Kabushiki KaishaExtraction method for odor and flavor producing ingredients of foods and flowers and products produced
US4157401 *24 Apr 19785 Jun 1979Life Savers, Inc.Chewing gum having improved flavor duration and shelf-life
US4158708 *4 Mar 197719 Jun 1979Societe D'assistance Technique Pour Produits Nestle S.A.Spice extract
US4198432 *28 Jul 197815 Apr 1980Studiengesellschaft Kohle MbhProcess for the production of spice extracts
US4208431 *20 Oct 197817 Jun 1980Life Savers, Inc.Long-lasting chewing gum having good processibility and method
US4250196 *9 Oct 197910 Feb 1981Life Savers, Inc.Center-filled chewing gums
US4316915 *26 Feb 198123 Feb 1982Life Savers, Inc.Center-filled chewing gums
US4318906 *23 Jun 19809 Mar 1982Establissement RinroneMedicinal composition for external use for treating wounds
US4380506 *25 Mar 198119 Apr 1983Lion CorporationProcess for producing preservatives
US4431680 *22 Oct 198114 Feb 1984International Flavors & Fragrances Inc.Process for augmenting or enhancing the aroma or taste of a peppermint oil based oral hygiene flavor by adding thereto methyl substituted oxobicyclo-4,4,0-decane derivatives
US4735358 *3 Mar 19875 Apr 1988Daiken Iko Kabushiki KaishaMethod and apparatus of vaporizing active substances
US4803082 *28 Oct 19877 Feb 1989Warner-Lambert CompanyFlavor and sweetness enhancement delivery systems and method of preparation
US4919149 *8 Jul 198824 Apr 1990Stang Michael AndrewContraception and flavor delivery system
US4923685 *28 Jul 19888 May 1990Henkel Kommanditgesellschaft Auf AktienAntimicrobial flavored compositions having particular utility as mouth washes
US4923865 *6 Apr 19898 May 1990U C B Societe AnonymeSubstituted 1-(1H-imidazol-4-yl)alkyl-benzamides as anti-ischemics and as alpha-2-adrenergic receptor agonists
US4925688 *8 Sep 198815 May 1990Daniel VoituriezMethod of diffusing essential oils and oleo-resins of spices in a carrier solution
US4935104 *13 Nov 198719 Jun 1990BiolandesProcess for the continuous hydro-distillation of plants
US4945087 *31 Mar 198831 Jul 1990Warner-Lambert CompanyTaste masking of thymol
US4985265 *12 Dec 198915 Jan 1991L'air Liquide, Society Anonyme Pour L'etude Et L'exploitation Des Procedes Georges ClaudeProcess for extraction of spices
US4990329 *3 Nov 19885 Feb 1991The Procter & Gamble CompanyComposition for treating oral diseases
US4994262 *25 May 198919 Feb 1991The Procter & Gamble CompanyOral compositions
US5015464 *13 Jun 198914 May 1991Amway CorporationAntiplaque chewing gum
US5017397 *25 Apr 199021 May 1991Uy NguyenProcess for extracting antioxidants from Labiatae herbs
US5023020 *14 Mar 199011 Jun 1991Shimizu Construction Co., Ltd.Method for supplying aromas, apparatus therefore and facilities provided with same
US5030459 *7 Nov 19899 Jul 1991Warner-Lambert CompanyHigh impact mint flavor for high base chewing gum
US5032387 *6 Nov 198616 Jul 1991Princeton Pharmaceutical Inc.Dental and oral hygiene preparations
US5091117 *16 Apr 199025 Feb 1992Nabisco Brands, Inc.Process for the removal of sterol compounds and saturated fatty acids
US5093145 *5 Jul 19903 Mar 1992DaregalProcess for treating an aromatic plant or herb, or a plant containing essential oils
US5094843 *10 Sep 199010 Mar 1992Beecham Inc.Antimicrobial toothpaste
US5110583 *10 Dec 19905 May 1992The Procter & Gamble CompanyPeroxy acids composition for oral treatment
US5110608 *9 Mar 19905 May 1992Warner-Lambert CompanyChewing gums having longer lasting sweetness
US5120558 *1 May 19919 Jun 1992Norac Technologies Inc.Process for the supercritical extraction and fractionation of spices
US5227183 *25 Jul 199113 Jul 1993Mccormick & Company, Inc.Process for preparing dehydrated aromatic plant products and the resulting products
US5277910 *11 Dec 199211 Jan 1994Mate HidvegiProcess for the preparation of a pharmaceutical composition selectively lowering the blood-lipid level
US5298238 *7 Nov 199129 Mar 1994Warner-Lambert CompanyLiquid oral compositions comprising deterpenated and fractionated flavor oils
US5403587 *22 Apr 19934 Apr 1995Eastman Kodak CompanyDisinfectant and sanitizing compositions based on essential oils
US5433949 *11 Mar 199318 Jul 1995Skw Trostberg AktiengesellschaftProcess for the production of natural antioxidants
US5487902 *19 Sep 199430 Jan 1996Fertin Laboratories Ltd. (Dansk Tyggegummi Fabrik A/S)Chewing gum composition with accelerated, controlled release of active agents
US5512285 *14 Feb 199430 Apr 1996Advanced Phytonics LimitedFragrance extraction
US5525260 *18 Feb 199211 Jun 1996Nestec S.APreparation of spice extract antioxidant in oil
US5527552 *9 Dec 199418 Jun 1996Kalamazoo Holdings, Inc.Lipid-soluble green tea catechin antioxidant solutions
US5633027 *7 Jun 199527 May 1997Fuisz Technologies Ltd.Confectioneries containing stabilized highly odorous flavor component delivery systems
US5723106 *21 Jan 19973 Mar 1998Warner-Lambert CompanyReduced alcohol mouthwash antiseptic and antiseptic preparation
US5858370 *22 Aug 199412 Jan 1999Scottish Agricultural CollegeBeneficial effects of plant volatile oils
US5858446 *28 Aug 199512 Jan 1999Byron Australia Pty LtdProcessed fresh herbs and method of making
US5891422 *10 Oct 19966 Apr 1999Warner-Lambert CompanyAntimicrobial composition containing a C3 -C6 alcohol
US5900230 *18 Aug 19974 May 1999Squigle, Inc.Dental products to treat and prevent periodontal disease
US6013304 *12 Dec 199711 Jan 2000Kalamazoo Holdings, Inc.High temperature countercurrent solvent extraction of herb or spice solids
US6022551 *20 Jan 19988 Feb 2000Ethicon, Inc.Antimicrobial composition
US6027716 *2 Apr 199722 Feb 2000Farmo-Nat Ltd.Synergistic herbal extracts
US6042812 *26 Nov 199628 Mar 2000The Procter & Gamble CompanyFlavor systems for oral care products
US6169118 *4 Nov 19992 Jan 2001Block Drug Company, Inc.Flavor blend for masking unpleasant taste of zinc compounds
US6235267 *23 Apr 199922 May 2001Pfizer Inc.Taste masking of phenolics using citrus flavors
US6235318 *21 Jan 199922 May 2001Charles M. Lombardy, Jr.Effervescent chewing gum
US6245309 *23 Dec 199712 Jun 2001H2-Tech S.A.R.LMethod and devices for producing hydrogen by plasma reformer
US6248309 *19 Aug 199919 Jun 2001Optiva CorporationGums containing antimicrobial agents
US6248343 *13 Dec 199919 Jun 2001Ethicon, Inc.Therapeutic antimicrobial compositions
US6338861 *26 Mar 199915 Jan 2002Shiseido Company, Ltd.Process of production of natural flavor or fragrance
US6346281 *5 May 200012 Feb 2002Scentsible Life Products, A Division Of Laid Back Designs Ltd.Antimicrobial composition formulated with essential oils
US6348187 *13 Jan 199719 Feb 2002Warner-Lambert CompanyPeroxide/essential oils containing mouthwash compositions and two-part mouthwash systems
US6365130 *23 Nov 19982 Apr 2002Agion Technologies L.L.C.Antimicrobial chewing gum
US6365209 *7 Feb 20012 Apr 2002Capricorn Pharma, Inc.Confectionery compositions and methods of making
US6379652 *16 Oct 200030 Apr 2002Colgate Palmolive CompanyOral compositions for reducing mouth odors
US6419903 *20 Aug 200116 Jul 2002Colgate Palmolive CompanyBreath freshening film
US6426085 *24 May 200030 Jul 2002Josman Laboratories Inc.Use of bismuth-containing compounds in topical oral dosage forms for the treatment of halitosis
US6521216 *10 Nov 200018 Feb 2003The Procter & Gamble CompanyDual phase stannous oral compositions
US6555094 *10 Nov 200029 Apr 2003The Procter & Gamble CompanyStannous oral compositions
US6579513 *3 Jan 200217 Jun 2003Playtex Products, Inc.Hygiene mouthspray composition
US6585961 *30 Nov 20011 Jul 2003Richard F. StockelAntimicrobial compositions
US6592912 *22 Jun 200015 Jul 2003Wm. Wrigley Jr. CompanyMethod of controlling release of antimicrobial agents from chewing gum and gum produced thereby
US6741954 *19 Dec 200125 May 2004Symrise Gmbh & Co. KgSelection method for odorants
US6846498 *13 Nov 200125 Jan 2005Scentsible Life Products, A Divison Of Laid Back Designs Ltd.Antimicrobial composition formulated with essential oils
US6855349 *7 Dec 199815 Feb 2005Kemin Industries, Inc.Method for simultaneous extraction of essential oils and antioxidants from Labiatae species and the extract products thereof
US6858214 *3 Mar 200022 Feb 2005Biotec AsaUse of nanoscalar water-soluble β-(1,3) glucans
US6902738 *19 Mar 20027 Jun 2005Josman Laboratories, Inc.Topical oral dosage forms containing bismuth compounds
US6921539 *18 Feb 200326 Jul 2005Dusan NinkovAntimicrobial therapeutic compositions and method of use
US6996919 *12 Mar 200214 Feb 2006Bionorica AgProcess for obtaining dry extracts under mild conditions
US7037543 *18 May 20012 May 2006Kalsec, IncorporatedMethod of extending color life of modified atmosphere packaged fresh red meat using Labiatae plant extracts
US7196117 *25 Nov 200127 Mar 2007Laboratorios Miret, S.A.Use of cationic surfactant as activity enhancer in deodorants and oral care
US20020068101 *13 Nov 20016 Jun 2002Death S. SamuelAntimicrobial composition formulated with essential oils
US20020081341 *30 Aug 200127 Jun 2002Cheryl SottMethod, apparatus, and system for customizing essential oil formulations
US20030068283 *22 Aug 200210 Apr 2003Unilever Home & Personal Care Usa, Division Of Conopco, Inc.Composition
US20030077232 *22 Aug 200224 Apr 2003Unilever Home & Personal Care Usa, Division Of Conopco, Inc.Composition
US20040067277 *14 Jul 20038 Apr 2004Wm. Wrigley Jr. CompanyMethod of controlling release of antimicrobial agents in chewing gum and gum produced thereby
US20040081713 *25 Jun 200329 Apr 2004Maxwell James RoyBreath freshening and oral cleansing product with magnolia bark extract
US20050008732 *11 Jul 200313 Jan 2005Petros GebreselassieChewing gum and confectionery compositions containing a stain removing complex, and methods of making and using the same
US20050228122 *31 Mar 200413 Oct 2005General Electric CompanyEsteramide compositions, copolymers and blends thereof
US20060013779 *14 Jul 200519 Jan 2006Dodds Michael W JBreath freshening and oral cleansing product with magnolia bark extract in combination with surface active agents
US20060088481 *17 May 200527 Apr 2006Athanikar Narayan KTopical oral dosage forms containing bismuth compounds
US20060120975 *29 Sep 20058 Jun 2006Colgate-Palmolive CompanyOral care composition comprising a phenolic compound and antioxidant vitamins and vitamin derivatives
US20060134023 *21 Dec 200422 Jun 2006Shira PilchOral care malodor composition
US20070031579 *1 Aug 20068 Feb 2007Draanen Nanine A VNatural product flavor concentrates as liquid spices: formulation and dispensing
US20070065394 *15 Nov 200422 Mar 2007Pinney Virginia RCompositions effective in altering the perception of malodor
US20070077210 *21 Nov 20065 Apr 2007Petros GebreselassieChewing gum and confectionery compositions containing a stain removing complex, and methods of making and using the same
US20070077343 *30 Sep 20055 Apr 2007Ma Sheng XProcess of concentrating tea and/or herbal aroma and beverages or flavors using the resulting concentrated aroma
US20070082018 *28 Sep 200612 Apr 2007Jochen WeissStabilized antimicrobial compositions and related methods of preparation
US20070166246 *2 Mar 200519 Jul 2007Toyo Shinyaku Co., Ltd.Composition for oral cavity
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US20110059205 *4 Sep 201010 Mar 2011Sylvia GaysinskyBotanical extracts and flavor systems and methods of making and using the same
WO2011029077A24 Sep 201010 Mar 2011Sensient Flavors LlcBotanical extracts and flavor systems and methods of making and using the same
Classifications
U.S. Classification424/734, 424/756, 424/747, 426/655, 424/739, 424/745, 424/746, 424/725, 424/755
International ClassificationA61K36/67, A61K36/534, A61K36/53, A61K36/00, A61K36/906, A61K36/54, A23L1/28, A61K36/31, A61K36/537, A61P1/02
Cooperative ClassificationA61K36/54, A61K36/282, A61K36/53, A61K36/23, A61K36/9068, A61K36/537, A61K36/61, A61K36/67, A61K36/31, A61K36/899, A61K36/235, A61K36/8962
European ClassificationA61K36/54, A61K36/282, A61K36/537, A61K36/23, A61K36/67, A61K36/899, A61K36/235, A61K36/61, A61K36/53, A61K36/8962, A61K36/31, A61K36/9068
Legal Events
DateCodeEventDescription
13 May 2009ASAssignment
Owner name: SENSIENT FLAVORS LLC, INDIANA
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HUGHES, KENNETH JOHN;GAYSINSKY, SYLVIA;BROWNING, ROGER MICHAEL;REEL/FRAME:022675/0225;SIGNING DATES FROM 20090422 TO 20090510