WO2001035918A1 - Compositions de flaveur et d'arome de menthe - Google Patents

Compositions de flaveur et d'arome de menthe Download PDF

Info

Publication number
WO2001035918A1
WO2001035918A1 PCT/US2000/031266 US0031266W WO0135918A1 WO 2001035918 A1 WO2001035918 A1 WO 2001035918A1 US 0031266 W US0031266 W US 0031266W WO 0135918 A1 WO0135918 A1 WO 0135918A1
Authority
WO
WIPO (PCT)
Prior art keywords
cysteine
composition according
flavor
oil
mint
Prior art date
Application number
PCT/US2000/031266
Other languages
English (en)
Inventor
Lawrence L. Buckholz, Jr.
Brian Byrne
Original Assignee
J. Manheimer, Inc.
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 J. Manheimer, Inc. filed Critical J. Manheimer, Inc.
Priority to AU16076/01A priority Critical patent/AU1607601A/en
Publication of WO2001035918A1 publication Critical patent/WO2001035918A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • This invention relates to mint flavor and aroma compositions and coolant compositions suitable for use in foodstuffs, tobacco products, fragrances and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.
  • Mint oils and mint flavors are used to flavor confections (sugar candy, breath mints, chewing gum etc.), as well as oral care products ( toothpaste, mouthwash, etc.), tobacco and smoking articles ( snuff, cigarettes, etc.).
  • Mint oils are used to fragrance topically applied materials (perfume, lip balms, lotions, etc.), as well as other fragrance applications (room deodorizers, soaps, cleaning products, etc.).
  • Mint oils and mint flavors are used to deliver topical cooling in the oral cavity (mouthwash, chewing gum etc.) as well as on the skin (colognes, lotions, bandages etc.) SUMMARY OF THE INVENTION
  • Mint oils, mint flavors and flavors containing chemical components found in mint are used widely in flavoring edible substances and topically applied materials.
  • the present invention provides for the treatment of such oils and flavors with cysteine, its salts, precursors or derivatives thereof.
  • the resultant product possesses properties which include: a) a stronger mint flavor; b) enhanced sweetness; c) more fresh picked flavor; d) a stronger cooling effect; and e) a creamy rich mouthfeel.
  • the products of this invention allow one to use lower concentrations of mint flavors or oils in products to achieve these effects with the product additionally possessing greater fresh picked character, cooling and creamy mouthfeel.
  • a greater flavor strength and impact can be achieved without the bitterness associated with high menthol containing products.
  • the products of this invention may be used in coolant compositions.
  • the inventive flavor compositions provide for a mint flavor stronger in flavor and enhances the sweetness in edible compositions.
  • the mint flavors are fresher (more characteristic of fresh picked mint), with a stronger cooling effect.
  • a secondary characteristic is the development of a creamy rich mouthfeel which compliments the above organoleptic sensations
  • the cysteine flavor or aroma compositions of the present invention comprise a treated mint oil, flavor or aroma obtained by mixing said mint oil flavor or aroma with cysteine, a salt or ester thereof, a cysteine precursor or a cysteine derivative, optionally in the presence of a solvent.
  • the process by which the treated mint flavors or aromas are obtained vary in time, temperature, solvent and source of cysteine. How this is achieved is limited to the resourcefulness of those skilled in the art and not meant to be the limiting factor of this invention
  • the temperature for the mixing process may range from low temperatures to high temperatures and the process may be conducted under atmospheric conditions or pressure. In a preferred embodiment, the temperature for the process may range from room temperature (about 20°C) to about 110°C. Depending upon the source of cysteine and contact time needed to complete the process, temperatures above 110°C to about 250°C, with commensurably shorter contact times, may be used.
  • This source of cysteine in the present invention includes cysteine itself, as well as its salts and ester forms. Preferred are the inorganic and organic salts of cysteine, with cysteme hydrochloride being especially preferred.
  • carboxylic acid alkyl esters of cysteine are also preferred.
  • these sources of cysteine are well known in the art and are obtained either commercially or by processes known in the art.
  • the source of cysteine may also be precursors of cysteine, such as its amino acid esters. Again, these precursors are well known in the art and are obtained either commercially or by processes known in the art.
  • Derivatives of cysteine include the cysteine adducts obtainable by the reaction of cysteine or an ester or salt thereof with an ⁇ , ⁇ -unsaturated carbonyl-containing compound. These adducts are described in copending application USSN 09/440,591, entitled Flavor Freshness Enhancers, herein incorporated by reference.
  • the mint flavor and aroma compounds for the invention and aroma compounds can be, for example, mint oils or flavors made from mint oil. These flavor and aroma compounds can be artificial or derived form natural sources, whether crude, purified or fractionated.
  • the mint flavor and aroma compositions are well know in the flavor art and may be obtained commercially or through processes known in the art.
  • the ratio of substrate oil or flavor to cysteine can be varied to achieve a particular economic goal, but is not limited to large excesses of one ingredient or the other.
  • cysteine be used in parts per million to a one to one weight ratio to the mint oil.
  • cysteine When treating distilled whole mint oils it is economically advantageous to treat about 99.9 parts of mint oil with about 0.1 parts cysteine with the product being used directly "as is".
  • cysteine In the case of highly purified fractions, nearly one to one ratios of cysteine to the fraction are most effective, with the product being further diluted in other flavors or oils to impart an enhanced sweetness, flavor strength and coolness.
  • a wide range of solvents may be used in the inventive process.
  • the solvents include those which are commonly used in foodstuffs, cosmetics and pharmaceutical preparations. It is also possible to use non-edible solvents, provided that they are removed by a removal step.
  • ethanol, water or mixtures thereof are used as solvents. Also preferred is the use of no solvent.
  • the pH can be varied depending upon the solvent used, if any, and the cysteine source. Other considerations are conditions necessary to generate cysteine from a precursor or derivative.
  • the preferred embodiment is a pH of about 1 to about 10, although, this is not intended to limit the scope of the invention.
  • inventive mint flavor and aroma compositions may also be formulated in coolant compositions where the inventive compositions are combined with other coolant materials. It is well known in the art e.g. U.S. Patent 5,451,404 and references cited therein all herein incorporated by reference, that multiple coolants synergize and amplify the cooling of single coolants. The present compositions also synergize and amplify the effect of single coolants.
  • the coolants which may be used in these compositions, are well known in the art and may be obtained commercially or through a known process.
  • Suitable coolants include, for example, menthol, N-ethyl-p- methane-3-carboxamide (WS-3), N-2,3-trimethyl-2-isopropyl butamide (WS-23), 1- menthone glycerin ketal, 3-1-menthoxy propane- 1,2-diol or monomenthyl succinate or its salts.
  • Such compositions, as well as the amount of mint flavor or aroma to add to these compositions is well known to one skilled in the art.
  • the mint flavor and aroma compositions may be used in a wide range of products and fragrances such as of foodstuffs, tobacco products, pharmaceuticals, oral care products, and sweeteners.
  • Such products, as well as the amount of flavor or aroma to add to these products would be well known to one skilled in the art.
  • Especially preferred food products include confectioneries such as chewing gums.
  • Especially preferred oral care products include mouthwashes or toothpastes.
  • Example 2 The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spearmint oil was used as is.
  • Example 2 The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spearmint oil was used as is.
  • Example 2 The above ingredients were added to a 500 ml round bottom flask equipped with a reflux condenser, mechanical stirrer and pot thermometer. The contents were heated over 20 minutes to a temperature of 104°C and the temperature held for one hour. The contents were cooled to room temperature and the phase separated. The treated spear
  • a solution of treated spearmint oil from Example 1 was made by using 0.1 g treated spearmint oil with 9.9 g ethanol.
  • Example 4 Product of Example 3 was compared against the untreated product as in Example 2.
  • the treated peppermint oil was stronger, sweeter and cooler than untreated oil.
  • Example 1 The above ingredients were treated as in Example 1.
  • the product of Example 5 were evaluated as in Example 2.
  • the treated carvone, product of Example 5, was sweeter, stronger in flavor, fresher tasting and surprisingly was cool tasting relative to the untreated material.
  • Chewing gum compositions were prepared using the formulations set forth below. The formulations were prepared by melting the gum base at a temperature of about 85 to 90°C and then adding with mixing the lecithin followed by adding the corn syrup and
  • Example 9 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 8 with a lingering sweetness for 12 minutes.
  • Example 12 Product of Example 11 had high up front cooling which maintained for 15 minutes without bitterness development. Flavor was also stronger than Example 10 with a lingering sweetness for 12 minutes.
  • Example 12
  • Example 13 The above ingredients were treated as in Example 1 and evaluated as in Example 2.
  • the treated Fennel Oil was stronger in anethol notes, was sweeter and more cooling than the untreated material.
  • Example 13 The treated Fennel Oil was stronger in anethol notes, was sweeter and more cooling than the untreated material.
  • the treated peppermint oil was stronger in peppermint flavor, sweetness and coolness than untreated peppermint oil.
  • Example 14 The above ingredients were treated as in Example 1 and the product evaluated as in Example 2.
  • the product of Example 14 was stronger, sweeter and cooler than the untreated oil and was similar in character and strength to the product of Example 1.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Confectionery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention des compositions de flaveur et d'arôme de menthe adaptées à une utilisation dans des denrées alimentaires, des cosmétiques, des fragrances, des édulcorants et des agents pharmaceutiques. Cette invention concerne également un procédé de préparation des compositions de l'invention.
PCT/US2000/031266 1999-11-15 2000-11-14 Compositions de flaveur et d'arome de menthe WO2001035918A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16076/01A AU1607601A (en) 1999-11-15 2000-11-14 Mint flavor and aroma compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US44115999A 1999-11-15 1999-11-15
US09/441,159 1999-11-15

Publications (1)

Publication Number Publication Date
WO2001035918A1 true WO2001035918A1 (fr) 2001-05-25

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/031266 WO2001035918A1 (fr) 1999-11-15 2000-11-14 Compositions de flaveur et d'arome de menthe

Country Status (2)

Country Link
AU (1) AU1607601A (fr)
WO (1) WO2001035918A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009511682A (ja) * 2005-10-14 2009-03-19 トーマス フランク ホフマン アンド アンドレアス ドゥンケル タマネギフレーバー化合物および使用
US8865192B2 (en) 2006-07-07 2014-10-21 The Procter & Gamble Co Flavor oils with reduced sulfur content and use in oral care compositions
US9089163B2 (en) 2010-12-01 2015-07-28 Tobacco Research And Development Institute (Proprietary) Limited Feed mechanism
US9155769B2 (en) 2006-07-07 2015-10-13 The Procter & Gamble Co Flavor oils with reduced dimethyl sulfoxide content and use in oral compositions
US9462828B2 (en) 2009-03-09 2016-10-11 British American Tobacco (Investments) Limited Apparatus for introducing objects into filter rod material
CN109777613A (zh) * 2019-02-22 2019-05-21 深圳烟草工业有限责任公司 一种烟用薄荷香精
RU2724996C2 (ru) * 2015-06-30 2020-06-29 Вм. Ригли Джр. Компани Холодящие составы длительного действия
US20210315178A1 (en) * 2020-04-10 2021-10-14 Wild Flavors, Inc. Columbia

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3773523A (en) * 1971-04-26 1973-11-20 Int Flavors & Fragrances Inc Edible compositions and processes for making same
US4243679A (en) * 1978-04-22 1981-01-06 Adsara Jorge D S-(3-Methyl-2-butenyl)cysteine
US4331648A (en) * 1979-12-05 1982-05-25 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services N-Acetyl-cysteine protects against cardiac damage from subsequently-administered cardio-toxic anthra-cycline in cancer therapy
US4486403A (en) * 1982-01-01 1984-12-04 Gerald Mechanic Composition for and treatment of teeth
US4959369A (en) * 1985-07-09 1990-09-25 Salim Aws S M Synergistic combinations
US5286480A (en) * 1992-06-29 1994-02-15 The Procter & Gamble Company Use of N-acetylated amino acid complexes in oral care compositions
US5458879A (en) * 1994-03-03 1995-10-17 The Procter & Gamble Company Oral vehicle compositions
US5468777A (en) * 1984-03-19 1995-11-21 The Rockefeller University Method and agents for preventing and reversing the staining of teeth
US5560913A (en) * 1995-01-27 1996-10-01 The Procter & Gamble Company Pharmaceutical compositions
US5827852A (en) * 1993-04-30 1998-10-27 The Procter & Gamble Company Coated pharmaceutical compositions
US5906811A (en) * 1997-06-27 1999-05-25 Thione International, Inc. Intra-oral antioxidant preparations
US5922346A (en) * 1997-12-01 1999-07-13 Thione International, Inc. Antioxidant preparation

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3773523A (en) * 1971-04-26 1973-11-20 Int Flavors & Fragrances Inc Edible compositions and processes for making same
US4243679A (en) * 1978-04-22 1981-01-06 Adsara Jorge D S-(3-Methyl-2-butenyl)cysteine
US4331648A (en) * 1979-12-05 1982-05-25 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services N-Acetyl-cysteine protects against cardiac damage from subsequently-administered cardio-toxic anthra-cycline in cancer therapy
US4486403A (en) * 1982-01-01 1984-12-04 Gerald Mechanic Composition for and treatment of teeth
US5468777A (en) * 1984-03-19 1995-11-21 The Rockefeller University Method and agents for preventing and reversing the staining of teeth
US4959369A (en) * 1985-07-09 1990-09-25 Salim Aws S M Synergistic combinations
US5358705A (en) * 1992-06-29 1994-10-25 The Procter & Gamble Company Use of N-acetylated amino acid complexes in oral care compositions
US5286480A (en) * 1992-06-29 1994-02-15 The Procter & Gamble Company Use of N-acetylated amino acid complexes in oral care compositions
US5827852A (en) * 1993-04-30 1998-10-27 The Procter & Gamble Company Coated pharmaceutical compositions
US5458879A (en) * 1994-03-03 1995-10-17 The Procter & Gamble Company Oral vehicle compositions
US5560913A (en) * 1995-01-27 1996-10-01 The Procter & Gamble Company Pharmaceutical compositions
US5906811A (en) * 1997-06-27 1999-05-25 Thione International, Inc. Intra-oral antioxidant preparations
US5922346A (en) * 1997-12-01 1999-07-13 Thione International, Inc. Antioxidant preparation

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009511682A (ja) * 2005-10-14 2009-03-19 トーマス フランク ホフマン アンド アンドレアス ドゥンケル タマネギフレーバー化合物および使用
US8865192B2 (en) 2006-07-07 2014-10-21 The Procter & Gamble Co Flavor oils with reduced sulfur content and use in oral care compositions
US9155769B2 (en) 2006-07-07 2015-10-13 The Procter & Gamble Co Flavor oils with reduced dimethyl sulfoxide content and use in oral compositions
EP2054494B2 (fr) † 2006-07-07 2016-07-27 The Procter and Gamble Company Huiles aromatiques ayant une teneur en soufre réduite et utilisation de celles-ci dans des compositions d'hygiène bucco-dentaire
US9462828B2 (en) 2009-03-09 2016-10-11 British American Tobacco (Investments) Limited Apparatus for introducing objects into filter rod material
US9089163B2 (en) 2010-12-01 2015-07-28 Tobacco Research And Development Institute (Proprietary) Limited Feed mechanism
US9101166B2 (en) 2010-12-01 2015-08-11 Tobacco Research And Development Institute (Proprietary) Limited Feed mechanism
US10092032B2 (en) 2010-12-01 2018-10-09 Tobacco Research And Development Institute (Proprietary) Limited Feed mechanism
RU2724996C2 (ru) * 2015-06-30 2020-06-29 Вм. Ригли Джр. Компани Холодящие составы длительного действия
CN109777613A (zh) * 2019-02-22 2019-05-21 深圳烟草工业有限责任公司 一种烟用薄荷香精
US20210315178A1 (en) * 2020-04-10 2021-10-14 Wild Flavors, Inc. Columbia

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