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WO1998018340A1 - Produits de gomme a macher contenant de la peryllartine - Google Patents

Produits de gomme a macher contenant de la peryllartine Download PDF

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Publication number
WO1998018340A1
WO1998018340A1 PCT/US1996/017227 US9617227W WO9818340A1 WO 1998018340 A1 WO1998018340 A1 WO 1998018340A1 US 9617227 W US9617227 W US 9617227W WO 9818340 A1 WO9818340 A1 WO 9818340A1
Authority
WO
WIPO (PCT)
Prior art keywords
chewing gum
perillartine
gum product
flavor
weight
Prior art date
Application number
PCT/US1996/017227
Other languages
English (en)
Inventor
Sonya S. Johnson
Robert J. Yatka
Original Assignee
Wm. Wrigley Jr. Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wm. Wrigley Jr. Company filed Critical Wm. Wrigley Jr. Company
Priority to CA002305769A priority Critical patent/CA2305769C/fr
Priority to PCT/US1996/017227 priority patent/WO1998018340A1/fr
Priority to AU74792/96A priority patent/AU7479296A/en
Priority to EP96937025A priority patent/EP0969732A4/fr
Priority to US09/297,427 priority patent/US6159509A/en
Publication of WO1998018340A1 publication Critical patent/WO1998018340A1/fr
Priority to US11/072,552 priority patent/US20050202118A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/068—Chewing gum characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds, extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides

Definitions

  • This invention relates generally to chewing gum products and, in particular, to chewing gum products which utilize perillartine to enhance and prolong sweetness and to provide improved sensory benefits.
  • This invention also relates to a method of preparing a chewing gum having enhanced and prolonged sweetness and improved sensory benefits.
  • Chewing gum compositions typically include gum base, flavoring and bulking and sweetening agents, as well as other optional ingredients such as softeners and coloring.
  • Bulking and sweetening agents often include sugar, glucose syrup and high-intensity sweeteners. High-intensity sweeteners are most commonly used in conjunction with sugarless sweeteners.
  • Sweetening agents generally are rapidly released from the chewing gum product. As a result of early release, chewing gum products tend to lose their sweetness after a short period of time. A need, therefore, exists for a method of improving and mamtaining the sweetness characteristics of chewing gum products.
  • Perillartine is a naturally occurring aldoxime sweetener found in the oil of Perilla namkemonsis Deone. It is 2000 times sweeter than sucrose.
  • the main component of Perilla oil is Perilla aldehyde.
  • Perillartine, the anti-aldoxime of this aldehyde can be formed synthetically from the reaction of Perilla aldehyde with hydroxylamine.
  • Perillartine which was first isolated and identified in 1920, can now synthesized from limonene. While permitted as a sweetener for tobacco in Japan, additional commercial applications are limited by its bitterness, its menthol-licorice taste and its very low water solubility.
  • Analogues of perillartine have been developed in an effort to increase its water solubility and minimize its bitterness while maintaining its high sweetness potency.
  • One such analogue, SRI Oxime V is a low molecular weight aldoxime that is 450 times sweeter than sucrose. This sweetener has heat stability in baked goods and adequate acid stability for soft drinks.
  • Another analogue is 8,9-epoxyperillartine, which is disclosed in U.S. Patent No. 3,699,132. This ingredient is more water soluble with little or no bitter aftertaste.
  • Japanese patent publication No. 1992-173056 discloses a chewing gum for preventing mouth odor and/or tooth decay.
  • Ingredients used for preventing mouth odor include substances from one or more types of plants from the Perilla family, such as rosemary or sage. Most of the other disclosures of perillartine show its use in oral compositions such as toothpaste, mouthwash, toothpowder or dental tablets for the reduction of caries or plaque or to provide other dental benefits.
  • the chewing gum has improved sweetness and sweetness duration.
  • Use of perillartine in chewing gum has a significant advantage over other sweeteners typically found in chewing gum in that perillartine is released very slowly with the flavor, thereby providing a chewing gum with a longer lasting sweetness.
  • the use of perillartine in gum not only improves sweetness and sweetness duration, but also, unexpectedly, provides unique trigeminal oral sensations that last throughout the entire chewing period.
  • the present invention relates to a method of improving and maintaining sweetness and improving sensory benefits of chewing gum products by adding perillartine to the chewing gum composition.
  • the invention also includes chewing gum products containing perillartine.
  • the invention is a chewing gum product having prolonged sweetness duration and improved sensory benefits comprising from about 5% to about 95% by weight gum base, from about 5% to about 95% by weight bulking and sweetening agents, from about 0.1% to about 15% by weight flavor and from about 0.005% to about
  • the invention is a method of making a chewing gum product with prolonged sweetness duration and improved sensory benefits comprising the steps of forming a chewing gum composition comprising from about 5% to about 95% by weight gum base, from about 5% to 95% by weight bulking and sweetening agents from about 0.1%) to about 15% by weight flavor; and adding from about 0.005% to about 0.5% by weight perillartine to the chewing gum composition.
  • perillartine is added to chewing gum products to improve sweetness and prolong sweetness duration in chewing gum.
  • the unexpected result is that perillartine also provides improved and long lasting sensory benefits.
  • These sensory benefits result from stimulation of the trigeminal nerve and include, but are not limited to, tingling, numbing, mouth coating and cooling/warming sensations.
  • the trigeminal effects also enhance the flavor of the chewing gum. These attributes could be very useful in giving the impression of long lasting flavor in products designed to give breath freshness or products designed to provide dental benefits.
  • FIG. 1 is a graph comparing the trigeminal effects in a chewing gum containing perillartine according to the present invention with the trigeminal effects in a chewing gum without perillartine.
  • chewing gum also includes bubble gum and the like. All percentages are weight percentages unless otherwise specified.
  • Trigeminal effects result when certain chemical irritants stimulate the trigeminal nerve ends causing sensations in the mucosa of the eyes, nose and mouth. Trigeminal effects are not a taste, such as sweet or sour, nor an odor. Rather, trigeminal effects are physical oral sensations such as, for example, coolness from menthol or heat from cinnamon or pepper flavors.
  • the trigeminal effects resulting from the inclusion of perillartine in chewing gum are described as tingling, numbing, mouth coating and cooling/warming sensations.
  • the trigeminal effects also impart an enhanced flavor to the chewing gum product.
  • Analysis of chewed gum containing perillartine indicates that perillartine releases with the flavor and that a substantial portion of perillartine (about 90%) remains in the gum after 20 minutes of chewing. After 40 minutes of chewing, about 80% of the perillartine still remains in the gum.
  • the unique sensory attributes obtained from perillartine remain during the entire chewing period.
  • the sweetness of a chewing gum composition is enhanced by adding perillartine, generally in an amount ranging from about 50 ppm to about 5,000 ppm, more preferably from about 100 ppm to about 2,000 ppm and most preferably from about 250 ppm to about 1,000 ppm. It is believed that analogues of perillartine may also be used in the present invention, and it is expected that some analogues may give the same trigeminal effects. Because the analogues are more water soluble, however, the trigeminal effects provided by them may not be expected to remain in the gum for the entire chewing period.
  • Perillartine is a white, crystalline powder with a molecular weight of 165.2 and is also known as 4-isopropenyl-l-cyclohexene-l-carboxaldehyde alpha antioxime. Perillartine is available from Sigma Chemical Company of St. Louis, Missouri. Perillartine may be added to chewing gum directly in its powder form or after first dissolving the powder in solvent, preferably flavor or flavor oil.
  • a typical chewing gum generally includes a water soluble bulk portion, a water insoluble chewing gum base portion and one or more flavoring agents. The water soluble portion dissipates over a period of time during chewing. The gum base portion is retained in the mouth throughout the chewing process.
  • the insoluble gum base generally includes elastomers, elastomer plasticizers (resins), fats, oils, waxes, softeners and inorganic fillers.
  • the elastomers may include polyisobutylene, isobutylene-isoprene copolymer, styrene butadiene copolymer and natural latexes such as chicle.
  • the resins may include polyvinyl acetate and terpene resins. Low molecular weight polyvinyl acetate is a preferred resin.
  • Fats and oils may include animal fats such as lard and tallow, vegetable oils such as soybean and cottonseed oils, hydrogenated and partially hydrogenated vegetable oils and cocoa butter.
  • Commonly used waxes include petroleum waxes such as paraffin and microcrystalline wax, natural waxes such as beeswax, candellia, carnauba and polyethylene wax.
  • the gum base typically also includes a filler component such as calcium carbonate, magnesium carbonate, talc, dicalcium phosphate and the like; softeners, including glycerol monostearate and glycerol triacetate; and optional ingredients such as antioxidants, color and emulsifiers.
  • the gum base constitutes about 5-95% by weight of the chewing gum composition, more typically about 10-50% by weight of the chewing gum, and most commonly about 20-30%) by weight of the chewing gum.
  • the water soluble portion of the chewing gum may include softeners, bulk sweeteners, high-intensity sweeteners, flavoring agents and combinations thereof.
  • Softeners are added to the chewing gum in order to optimize the chewability and mouth feel of the gum.
  • the softeners which are also known as plasticizers or plasticizing agents, generally constitute about 0.5-15% by weight of the chewing gum.
  • the softeners may include glycerin, lecithin and combinations thereof.
  • Aqueous sweetener solutions such as those containing sorbitol, hydrogenated starch hydrolysates, corn syrup and combinations thereof may also be used as softeners and binding agents in chewing gum.
  • Bulk sweeteners constitute about 5-95% by weight of the chewing gum, more typically about 20-80% by weight of the chewing gum and most commonly about 30-60% by weight of the chewing gum.
  • Bulk sweeteners may include both sugar and sugarless sweeteners and components.
  • Sugar sweeteners may include saccharide containing components including but not limited to sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup solids, glucose syrup and the like, alone or in combination.
  • Sugarless sweeteners include components with sweetening characteristics but are devoid of the commonly known sugars.
  • Sugarless sweeteners include but are not limited to sugar alcohols such as sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitol and the like, alone or in combination.
  • High-intensity sweeteners may also be present and are commonly used with sugarless sweeteners. When used, high-intensity sweeteners typically constitute about 0.001-5%) by weight of the chewing gum, preferably about 0.01-1%) by weight of the chewing gum. Typically, high-intensity sweeteners are at least twenty times sweeter than sucrose. These may include, but are not limited to sucralose, aspartame, salts of acesulfame, alitame, saccharin and its salts, cyclamic acid and its salts, glycyrrhizin, di ydrochalcones, thaumatin, monellin and the like, alone or in combination.
  • Combinations of sugar and/or sugarless sweeteners may be used in chewing gum.
  • the sweetener may also function in the chewing gum in whole or in part as a water soluble bulking agent.
  • the softener may provide additional sweetness, such as when aqueous sugar or alditol solutions are used in the gum composition.
  • perillartine may be used in all types of sugar and sugarless chewing gum.
  • Flavor should generally be present in the chewing gum in an amount within the range of about 0.1-15% by weight of the chewing gum, preferably about 0.2-5% by weight of the chewing gum and most preferably about 0.5-3% by weight of the chewing gum.
  • 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, cinnamon, anise and the like. Artificial flavoring agents and components may also be used in the flavor ingredient of the invention. Natural and artificial flavoring agents may be combined in any sensorally acceptable fashion.
  • Perillartine may be used with various flavors such as spearmint, peppermint, fruit, cinnamon and eucalyptus.
  • perillartine is used with mint flavors and, even more preferably, with peppermint.
  • the perillartine is premixed with the flavor and then added to a chewing gum composition comprising gum base and bulking and sweetening agents.
  • Optional ingredients such as colors, emulsifiers, pharmaceutical agents, and additional flavoring agents may also be included in chewing gum.
  • the following gum formulations were made by premixing the perillartine with the peppermint flavor and then adding the perillartine/flavor mixture to the remaining ingredients.
  • Example 1 250 ppm perillartine
  • Example 2 500 ppm perillartine
  • Comparative Example A The samples were presented unidentified in a random order.
  • Example 1 v. Comparative Example A: Example 1 had a slight artificial sweetness, but was also more bitter than Example A. Example 1 also provided a slight warming or numbing sensation. 2.
  • Example 2 v. Comparative Example A: Example 2 had a higher sweetness and a higher amount of artificial sweetness than Example A. Example 2 also provided a tingling and numbing sensation.
  • Example 3 A quantitative time-intensity panel of eight trained judges was conducted to evaluate Inventive Example 3 against Comparative Example A. Panelists were asked to rate the intensity levels of bitterness, flavor, cooling and trigeminal effects of these two examples at intervals from 30 seconds to 20 minutes of chewing. Results showed that flavor, cooling and bitterness were all higher for Example 3 throughout the chewing period, but not to a statistically significant degree. Compared to Example A, Example 3 also had a higher sweetness throughout the chewing period and a statistically higher sweetness (95%> confidence level) at 4-minute and 8-minute intervals. Additionally, the trigeminal effects in Example 3 were statistically higher throughout the chewing period, as shown in Table I below and in FIG.
  • Example 3 which graphically illustrates the strength of the trigeminal effects in Example 3 as compared to the strength of the trigeminal effects in Example A on a scale of 1 to 9, with 9 being “extremely strong effects” and 1 being “minimal effects.”
  • the trigeminal effects were described as tingling, numbing, mouth coating and warming sensations.
  • Table I shows the average values of the trigeminal effects for Example 3 and Example A at various time intervals during a 20-minute chewing period. Confidence levels are also shown in Table I for the average values of the trigeminal effects from the eight panelists. The confidence levels indicate that there is a statistically significant difference between Inventive Example 3 and Comparative Example A.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Botany (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Confectionery (AREA)

Abstract

Une quantité d'environ 50 à 5000 mg/kg de péryllartine est ajoutée à de la gomme à mâcher pour obtenir une gomme à mâcher ayant une sucrosité améliorée et une durée de sucrosité prolongée. La péryllartine produit également dans la bouche des effets trigéminaux inattendus, tels que chatouillement, engourdissement, enduction buccale, et des sensations de fraîcheur/chaleur qui durent pendant tout le temps de mastication.
PCT/US1996/017227 1996-10-28 1996-10-28 Produits de gomme a macher contenant de la peryllartine WO1998018340A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002305769A CA2305769C (fr) 1996-10-28 1996-10-28 Produits de gomme a macher contenant de la peryllartine et methode de fabrication connexe
PCT/US1996/017227 WO1998018340A1 (fr) 1996-10-28 1996-10-28 Produits de gomme a macher contenant de la peryllartine
AU74792/96A AU7479296A (en) 1996-10-28 1996-10-28 Chewing gum products containing perillartine and method of making the same
EP96937025A EP0969732A4 (fr) 1996-10-28 1996-10-28 Produits de gomme a macher contenant de la peryllartine
US09/297,427 US6159509A (en) 1996-10-28 1996-10-28 Method of making chewing gum products containing perillartine
US11/072,552 US20050202118A1 (en) 1996-10-28 2005-03-03 Chewing gum products containing trigeminal stimulant and method of making the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1996/017227 WO1998018340A1 (fr) 1996-10-28 1996-10-28 Produits de gomme a macher contenant de la peryllartine

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/127,858 Continuation-In-Part US7025999B2 (en) 1996-10-28 2002-04-22 Chewing gum having prolonged sensory benefits

Publications (1)

Publication Number Publication Date
WO1998018340A1 true WO1998018340A1 (fr) 1998-05-07

Family

ID=22256027

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/017227 WO1998018340A1 (fr) 1996-10-28 1996-10-28 Produits de gomme a macher contenant de la peryllartine

Country Status (4)

Country Link
EP (1) EP0969732A4 (fr)
AU (1) AU7479296A (fr)
CA (1) CA2305769C (fr)
WO (1) WO1998018340A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6159509A (en) * 1996-10-28 2000-12-12 Wm. Wrigley Jr. Company Method of making chewing gum products containing perillartine
WO2001049125A1 (fr) * 1999-12-30 2001-07-12 Wm. Wrigley Jr. Company Libération contrôlée de périllartine dans de la gomme à mâcher
GB2423914A (en) * 2005-03-03 2006-09-13 Wrigley W M Jun Co Chewing gum containing a trigeminal stimulant
CN112841388A (zh) * 2021-01-28 2021-05-28 铜仁职业技术学院 一种含二氢杨梅素的降脂口香糖及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4627974A (en) * 1984-12-21 1986-12-09 Ici Americas Inc. Dentifrice formulation and method of treating teeth, mouth and throat therewith to reduce plaque accumulation and irritation
US4693888A (en) * 1983-08-11 1987-09-15 Lion Corporation Caries-preventive composition
US5095106A (en) * 1989-07-25 1992-03-10 Colgate-Palmolive Olgiosaccharide inhibition of Streptococcus pyogenes adhesion
US5242693A (en) * 1988-06-21 1993-09-07 Yoshie Kurihara Protein curuculin and application of the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4242323A (en) * 1979-08-22 1980-12-30 Vlock D G Plaque inhibiting oral composition
US5002759A (en) * 1989-07-25 1991-03-26 Colgate-Palmolive Company Oligosaccharide inhibition of Streptococcus pyogenes adhesion

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4693888A (en) * 1983-08-11 1987-09-15 Lion Corporation Caries-preventive composition
US4627974A (en) * 1984-12-21 1986-12-09 Ici Americas Inc. Dentifrice formulation and method of treating teeth, mouth and throat therewith to reduce plaque accumulation and irritation
US5242693A (en) * 1988-06-21 1993-09-07 Yoshie Kurihara Protein curuculin and application of the same
US5095106A (en) * 1989-07-25 1992-03-10 Colgate-Palmolive Olgiosaccharide inhibition of Streptococcus pyogenes adhesion

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0969732A4 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6159509A (en) * 1996-10-28 2000-12-12 Wm. Wrigley Jr. Company Method of making chewing gum products containing perillartine
WO2001049125A1 (fr) * 1999-12-30 2001-07-12 Wm. Wrigley Jr. Company Libération contrôlée de périllartine dans de la gomme à mâcher
GB2423914A (en) * 2005-03-03 2006-09-13 Wrigley W M Jun Co Chewing gum containing a trigeminal stimulant
CN112841388A (zh) * 2021-01-28 2021-05-28 铜仁职业技术学院 一种含二氢杨梅素的降脂口香糖及其制备方法

Also Published As

Publication number Publication date
CA2305769A1 (fr) 1998-05-07
CA2305769C (fr) 2003-09-16
EP0969732A1 (fr) 2000-01-12
EP0969732A4 (fr) 2000-04-05
AU7479296A (en) 1998-05-22

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