WO2000001321A1 - Methods and compositions for producing a cooling effect in tissues - Google Patents

Methods and compositions for producing a cooling effect in tissues Download PDF

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Publication number
WO2000001321A1
WO2000001321A1 PCT/US1999/015173 US9915173W WO0001321A1 WO 2000001321 A1 WO2000001321 A1 WO 2000001321A1 US 9915173 W US9915173 W US 9915173W WO 0001321 A1 WO0001321 A1 WO 0001321A1
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Prior art keywords
dimethyl ether
composition
tissue
aqueous solution
cooling
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Application number
PCT/US1999/015173
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French (fr)
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WO2000001321A9 (en
Inventor
Eugene H. Gans
Original Assignee
Gans Eugene H
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Publication date
Application filed by Gans Eugene H filed Critical Gans Eugene H
Priority to CA002303094A priority Critical patent/CA2303094A1/en
Priority to EP99933697A priority patent/EP1017334A1/en
Publication of WO2000001321A1 publication Critical patent/WO2000001321A1/en
Publication of WO2000001321A9 publication Critical patent/WO2000001321A9/en

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    • 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
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/005—Preparations for sensitive skin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • 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
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams

Definitions

  • This invention relates to techniques for the production of soothing, cooling sensations in tissues such as sensitive skin areas and mucous membranes.
  • Chloroform was once widely used for this purpose, but is no longer used because of its carcinogenic potential.
  • Camphor and aromatic oils have distinct flavors and odors and are sometimes irritating or sensitizing to certain tissues.
  • dimethyl ether (CH 3 -O-CH 3 ) is effective in producing a sensation of esthetic cooling.
  • Dimethyl ether may be applied to the target tissues in the form of a liquid or a gas arising from a liquid that is sprayed, swallowed, or applied with a bandage or other dressing. Alternatively, it may be applied as a lozenge, suppository, or other solid dosage form that releases the dimethyl ether to the target tissue.
  • the intensity and duration of the esthetic cooling effect is obtained when the dimethyl ether is applied at concentrations of as little as 1.0%, or even lower in formulations where availability and delivery to tissues is heightened or enhanced. It has also been discovered that this technique can enhance the perception of flavor of foods, beverage, and candies.
  • Dimethyl ether is a well-known and well-characterized chemical entity. Its principal commercial use is as a propellant for aerosols such as hair sprays. See, for example, "A New Era In Aerosol Propellants” J.J. Daily, Drug Cosmet. Ind.. Vol. 134, No. 2, Page 40 (1984). Because of its high volatility, it has also been used as a cryogenic agent for removing skin lesions. See U.S. Patent No. 5,516,505. Some of Dimethyl ether's physical properties are shown in Table 1.
  • dimethyl ether can be applied to skin and sensitive tissues to produce a sensation of esthetic cooling. This should not be confused with an actual lowering of temperature by means of evaporation or volatilization as described in U.S. Patent No. 5,516,505, as dimethyl ether is capable of producing this effect even in areas where evaporative cooling is not possible, such as the throat. Indeed, some of the preferred embodiments of this invention call for dimethyl ether to be applied in a manner which tends to produce very little evaporative cooling.
  • dimethyl ether Because of its high solubility in water, dimethyl ether is conveniently applied to the target tissue in the form of an aqueous solution. It can also be delivered in other suitable solvents or in systems where the gas is absorbed or entrapped. Aqueous solutions in excess of 30% by weight can be prepared and are useful in this invention. However, solutions of much lower concentration are typically employed.
  • Dimethyl ether is available from a variety of sources and is marketed by the E.I. DuPont Company under the trade name DYMEL A.
  • DME Dimethyl either
  • compounds such as viscosity builders which prolong its delivery and sensate effect, or compounds such as ethanol, carbon dioxide and others which can speed and heighten its delivery and sensate effect.
  • compounds known to create their own type of sensate effect on tissues such as menthol, glycyrrhizin, aromatic oils, capsaicin, and others, which can contribute to DME's unique sensate effect.
  • aqueous solution of dimethyl ether was prepared in the following manner.
  • DYMEL A brand dimethyl ether was obtained in the form of a cylinder of compressed gas.
  • a length of tubing was attached to the regulator valve of the tank and run into a 250 milliliter erlenmeyer flask containing 125 milliliters of distilled water. The tubing terminated in a fritted glass gas diffuser. The flask was maintained in an ice water bath to minimize evaporative loss.
  • Dimethyl ether gas was bubbled through the liquid, allowing the dimethyl ether to dissolve in the water. This process was used to produce solutions of approximately 2%, 5% and 10% by weight of dimethyl ether. Aliquots of these solutions were used in the following experiments to demonstrate the ability of dimethyl ether to produce a sensation of esthetic cooling.
  • a subject sipped a small volume of 2%, 5% and 10% dimethyl ether solutions and reported a distinct, penetrating sensation of esthetic cooling in the mouth and throat. Aliquots of these solutions were diluted to produce 1.0% and 0.5% dimethyl ether solutions and was again sipped by the subject. The sensation of esthetic cooling was still noticeable though less intense.
  • dimethyl ether solution An aliquot of 2% dimethyl ether solution was diluted to 1.0% and 0.5% and applied to sensitive skin areas including irritated eyelids, psoriatic skin, eczematous skin and fresh surgical sites. In each case, the subject reported a pleasant sensation of esthetic cooling.
  • Other liquid forms of dimethyl ether solutions have been prepared and found effective in the present invention.
  • dimethyl ether prepared in the manner described above, the following compositions were prepared: Three and 6% dimethyl ether solutions in a benzalkonium chloride anti-bacterial mouthwash, a 3% dimethyl ether solution in a syrup, a 2.0% dimethyl ether solution in a nasal spray of 1% penylephrine decongestant, a 1.0% and 2.5% dimethyl ether solutions in an aqueous phosphate enema solution and a 1.0% and 2.5% dimethyl ether solutions in a 5% vinegar vaginal douche.
  • the ordinary action of these preparations was supplemented by a pleasant and soothing sensation of esthetic cooling.
  • Confections, drops, troches, lozenges, gums and the like incorporating dimethyl ether can be formulated. These are useful as cough drops or cough lozenges, and are useful in cases of gum or mouth irritation and oral ulcers or sores. (This can also be accomplished by direct introduction of aqueous solutions of dimethyl ether described above or dimethyl ether solutions together with other solvents.)
  • Dermatological delivery systems containing dimethyl ether have been compounded by introducing dimethyl ether solution into the following products to obtain 4% concentrations: an oil-in-water moisturizing lotion, an oil-in-water anti-inflammatory hydrocortisone cream, a water-in-oil emulsion skin emollient lotion, and a protective diaper ointment.
  • an oil-in-water moisturizing lotion an oil-in-water anti-inflammatory hydrocortisone cream
  • a water-in-oil emulsion skin emollient lotion a protective diaper ointment.
  • Each of these dermatological products was used to treat sensitive skin in the areas of the chest, neck, groin, thighs and buttocks, and, in addition to their ordinary therapeutic action, produced a pleasant and soothing sensation of esthetic cooling.
  • the present invention may also be used in topical analgesics, including capsaicin on civamide containing preparations to enhance their effectiveness or appeal.
  • the taste sensation produced by various foods was enhanced by the addition of dimethyl ether.
  • the taste of liquors such as Gran Marnier and B&B were enhanced by the addition of 1% and 2% dimethyl ether. Similar effects can be obtained by introducing satiable concentrations of dimethyl ether into sodas, candies, and confections.

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Abstract

A technique for the production of soothing and cooling sensations in tissues such as sensitive skin areas and mucous membranes is provided. To produce a sensation of esthetic cooling, dimethyl ether may be applied to the target tissues in the form of a liquid or a gas arising from a liquid that is sprayed, swallowed, or applied with a bandage or other dressing. Alternatively, it may be applied as a lozenge, suppository, or other solid dosage form that releases the dimethyl ether to the target tissue. The intensity and duration of the esthetic cooling effect is obtained when the dimethyl ether is applied at minute concentrations. It has also been discovered that this technique can enhance the perception of flavor of foods, beverages, and candies.

Description

METHODS AND COMPOSITIONS FOR PRODUCING A COOLING EFFECT IN TISSUES
Field of the Invention
This invention relates to techniques for the production of soothing, cooling sensations in tissues such as sensitive skin areas and mucous membranes.
Background of the Invention
It has long been desired to be able to produce a cooling, soothing sensation in sensitive skin areas, including mucous membranes. In the past this has been achieved by use of substances such as chloroform or camphor. The sensation produced by these substances has been variously described as cooling, penetration, or a sense of spreading or a sense of opening up/cleaning out. This esthetic signaling effect shall be referred to herein as "esthetic cooling." In addition to being mildly pleasurable, this sensation is often genuinely soothing to sensitive or irritated tissues.
Compounds which are known to produce the esthetic cooling effect all suffer from a variety of drawbacks, some of them quite serious. Chloroform was once widely used for this purpose, but is no longer used because of its carcinogenic potential. Camphor and aromatic oils have distinct flavors and odors and are sometimes irritating or sensitizing to certain tissues.
It is therefore highly desirable to find a way to achieve this effect of esthetic cooling that is safe, convenient and effective.
Summary of the Invention
It has been discovered that dimethyl ether (CH3-O-CH3) is effective in producing a sensation of esthetic cooling. Dimethyl ether may be applied to the target tissues in the form of a liquid or a gas arising from a liquid that is sprayed, swallowed, or applied with a bandage or other dressing. Alternatively, it may be applied as a lozenge, suppository, or other solid dosage form that releases the dimethyl ether to the target tissue. The intensity and duration of the esthetic cooling effect is obtained when the dimethyl ether is applied at concentrations of as little as 1.0%, or even lower in formulations where availability and delivery to tissues is heightened or enhanced. It has also been discovered that this technique can enhance the perception of flavor of foods, beverage, and candies.
Detailed Description of the Invention
Dimethyl ether is a well-known and well-characterized chemical entity. Its principal commercial use is as a propellant for aerosols such as hair sprays. See, for example, "A New Era In Aerosol Propellants" J.J. Daily, Drug Cosmet. Ind.. Vol. 134, No. 2, Page 40 (1984). Because of its high volatility, it has also been used as a cryogenic agent for removing skin lesions. See U.S. Patent No. 5,516,505. Some of Dimethyl ether's physical properties are shown in Table 1.
Table 1 Physical Properties of Dimethyl Ether
Molecular Weight 44.07
Boiling Point -24.8°C
Density at 20°C 0.66 g/ml
Solubility in H2O at 20°C 35 wt %
It has been found that dimethyl ether can be applied to skin and sensitive tissues to produce a sensation of esthetic cooling. This should not be confused with an actual lowering of temperature by means of evaporation or volatilization as described in U.S. Patent No. 5,516,505, as dimethyl ether is capable of producing this effect even in areas where evaporative cooling is not possible, such as the throat. Indeed, some of the preferred embodiments of this invention call for dimethyl ether to be applied in a manner which tends to produce very little evaporative cooling.
Because of its high solubility in water, dimethyl ether is conveniently applied to the target tissue in the form of an aqueous solution. It can also be delivered in other suitable solvents or in systems where the gas is absorbed or entrapped. Aqueous solutions in excess of 30% by weight can be prepared and are useful in this invention. However, solutions of much lower concentration are typically employed.
Dimethyl ether is available from a variety of sources and is marketed by the E.I. DuPont Company under the trade name DYMEL A.
Other components may be added to the aqueous solution of Dimethyl either (DME) in order to advantageously modify its delivery. For instance, compounds such as viscosity builders which prolong its delivery and sensate effect, or compounds such as ethanol, carbon dioxide and others which can speed and heighten its delivery and sensate effect. Additionally, there are compounds known to create their own type of sensate effect on tissues, such as menthol, glycyrrhizin, aromatic oils, capsaicin, and others, which can contribute to DME's unique sensate effect.
An aqueous solution of dimethyl ether was prepared in the following manner. DYMEL A brand dimethyl ether was obtained in the form of a cylinder of compressed gas. A length of tubing was attached to the regulator valve of the tank and run into a 250 milliliter erlenmeyer flask containing 125 milliliters of distilled water. The tubing terminated in a fritted glass gas diffuser. The flask was maintained in an ice water bath to minimize evaporative loss. Dimethyl ether gas was bubbled through the liquid, allowing the dimethyl ether to dissolve in the water. This process was used to produce solutions of approximately 2%, 5% and 10% by weight of dimethyl ether. Aliquots of these solutions were used in the following experiments to demonstrate the ability of dimethyl ether to produce a sensation of esthetic cooling.
A subject sipped a small volume of 2%, 5% and 10% dimethyl ether solutions and reported a distinct, penetrating sensation of esthetic cooling in the mouth and throat. Aliquots of these solutions were diluted to produce 1.0% and 0.5% dimethyl ether solutions and was again sipped by the subject. The sensation of esthetic cooling was still noticeable though less intense.
An aliquot of 2% dimethyl ether solution was diluted to 1.0% and 0.5% and applied to sensitive skin areas including irritated eyelids, psoriatic skin, eczematous skin and fresh surgical sites. In each case, the subject reported a pleasant sensation of esthetic cooling. Other liquid forms of dimethyl ether solutions have been prepared and found effective in the present invention. Using a solution of dimethyl ether prepared in the manner described above, the following compositions were prepared: Three and 6% dimethyl ether solutions in a benzalkonium chloride anti-bacterial mouthwash, a 3% dimethyl ether solution in a syrup, a 2.0% dimethyl ether solution in a nasal spray of 1% penylephrine decongestant, a 1.0% and 2.5% dimethyl ether solutions in an aqueous phosphate enema solution and a 1.0% and 2.5% dimethyl ether solutions in a 5% vinegar vaginal douche. In each case, the ordinary action of these preparations was supplemented by a pleasant and soothing sensation of esthetic cooling.
Confections, drops, troches, lozenges, gums and the like incorporating dimethyl ether can be formulated. These are useful as cough drops or cough lozenges, and are useful in cases of gum or mouth irritation and oral ulcers or sores. (This can also be accomplished by direct introduction of aqueous solutions of dimethyl ether described above or dimethyl ether solutions together with other solvents.)
Dermatological delivery systems containing dimethyl ether have been compounded by introducing dimethyl ether solution into the following products to obtain 4% concentrations: an oil-in-water moisturizing lotion, an oil-in-water anti-inflammatory hydrocortisone cream, a water-in-oil emulsion skin emollient lotion, and a protective diaper ointment. Each of these dermatological products was used to treat sensitive skin in the areas of the chest, neck, groin, thighs and buttocks, and, in addition to their ordinary therapeutic action, produced a pleasant and soothing sensation of esthetic cooling. The present invention may also be used in topical analgesics, including capsaicin on civamide containing preparations to enhance their effectiveness or appeal.
The effect of esthetic cooling has also been produced using an aqueous solution of dimethyl ether that is sprayed onto the target tissue by means of an aerosol or atomizer. Other application methods within the scope of this invention will be apparent to those skilled in the art upon reading this specification.
The taste sensation produced by various foods was enhanced by the addition of dimethyl ether. For example, the taste of liquors such as Gran Marnier and B&B were enhanced by the addition of 1% and 2% dimethyl ether. Similar effects can be obtained by introducing satiable concentrations of dimethyl ether into sodas, candies, and confections.
The foregoing examples are non-limiting and the invention is defined only by the following claims.

Claims

Claims
I ΓÇó A method of producing a sensation of esthetic cooling in animal tissue comprising applying an efficacious amount of dimethyl ether to the tissue.
2. The method of claim 1 , wherein the dimethyl ether is in the form of an aqueous solution.
3. The method of claim 2, wherein the aqueous solution is sprayed onto the tissue.
4. The method of claim 1, wherein the dimethyl ether is provided in an oil- in-water emulsion.
5. The method of claim 1, wherein the dimethyl ether is provided in a dermatologically acceptable lotion.
6. The method of claim 1, wherein the dimethyl ether is provided in a protective ointment.
7. A method of soothing irritated or inflamed tissue comprising applying an efficacious amount of dimethyl ether to the tissue.
8. The method of claim 7, wherein the dimethyl ether is in the form of an aqueous solution.
9. The method of claim 7, wherein the aqueous solution is sprayed onto the tissue.
10. The method of claim 7, wherein the dimethyl ether is provided in an oil- in-water emulsion.
I I Γûá The method of claim 7, wherein the dimethyl ether is provided in a dermatologically acceptable lotion.
12. The method of claim 7, wherein the dimethyl ether is provided in a protective ointment.
13. The method of claim 7, wherein the aqueous solution is sprayed onto the tissue.
14. The method of claim 7, wherein the dimethyl ether is provided in an oil- in-water emulsion.
15. The method of claim 7, wherein the dimethyl ether is provided in a dermatologically acceptable lotion.
16. The method of claim 7, wherein the dimethyl ether is provided in a protective ointment.
17. A composition for the treatment of living tissues comprising an efficacious amount of dimethyl ether and a pharmacalogically acceptable carrier.
18. The composition of claim 17, wherein the carrier is a dermatologically acceptable vehicle.
19. The composition of claim 17, wherein the composition is a lozenge.
20. The composition of claim 17, wherein the composition is a syrup.
21. The composition of claim 17, wherein the composition is a suppository.
22. The method of claim 17, wherein the dimethyl ether is in the form of an aqueous solution.
23. The composition of claim 13, wherein the dimethyl ether is present in a concentration of at least 0.1 % by weight
24. The composition of claim 13, wherein the dimethyl ether is present in a concentration of at least 0.5% by weight.
25. The composition of claim 13, wherein the dimethyl ether is present in a concentration of at least 1.0% by weight.
26. The composition of claim 13, wherein the dimethyl ether is present in a concentration of at least 2.0% by weight.
27. A method of enhancing the taste sensation produced by food, comprising adding dimethyl ether to the food.
28. The method of claim 27, wherein the dimethyl ether is present in the food in a concentration of at least 0.1% by weight.
29. The method of claim 28, wherein the concentration of dimethyl ether is at least 1.0% by weight.
30. The method of claim 29, wherein the food is an alcoholic beverage.
31. The method of claim 29, wherein the food is a candy or confection.
32. The method of claim 29, wherein the food is a beverage.
PCT/US1999/015173 1998-07-02 1999-07-01 Methods and compositions for producing a cooling effect in tissues WO2000001321A1 (en)

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CA002303094A CA2303094A1 (en) 1998-07-02 1999-07-01 Methods and compositions for producing a cooling effect in tissues
EP99933697A EP1017334A1 (en) 1998-07-02 1999-07-01 Methods and compositions for producing a cooling effect in tissues

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US10936698A 1998-07-02 1998-07-02
US09/109,366 1998-07-02

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2807467A1 (en) 2000-04-05 2001-10-12 Peugeot Citroen Automobiles Sa INTERNAL COMBUSTION ENGINE FOR MOTOR VEHICLE
WO2013171018A3 (en) * 2012-05-16 2014-04-10 Symrise Ag Mixtures having improved cooling effect

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE CHEMICAL ABSTRACTS ON STN, No. 122:222882, RUSSELL, "Spray Formulation Having a Cooling Effect"; & WO 9504522 A1, 16 February 1995. *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2807467A1 (en) 2000-04-05 2001-10-12 Peugeot Citroen Automobiles Sa INTERNAL COMBUSTION ENGINE FOR MOTOR VEHICLE
WO2013171018A3 (en) * 2012-05-16 2014-04-10 Symrise Ag Mixtures having improved cooling effect
US9743685B2 (en) 2012-05-16 2017-08-29 Symrise Ag Mixtures having improved cooling effect

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WO2000001321A9 (en) 2000-07-27
CA2303094A1 (en) 2000-01-13
EP1017334A1 (en) 2000-07-12

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