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BR-112013022950-B1 - METHOD AND COMPOSITION FOR MASKING UNPLEASANT ODORS

BR112013022950B1BR 112013022950 B1BR112013022950 B1BR 112013022950B1BR-112013022950-B1

Abstract

MASKING OF UNPLEASANT ODORS. The present invention relates to a method of masking an unpleasant odor in an orally digestible or orally ingestible composition, including the addition of an amount of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one or a salt thereof for masking an unpleasant odor. The effect may be further improved by the addition of Compound 2 and/or 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof.

Inventors

  • Kimberley Gray
  • Yili Wang
  • SCOTT WAYNE KELLER

Assignees

  • GIVAUDAN SA

Dates

Publication Date
20260310
Application Date
20120314
Priority Date
20110314

Claims (6)

  1. 1. A method for masking an unpleasant odor in an orally acceptable or orally ingestible composition, characterized in that it comprises adding an amount for masking the unpleasant odor of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one of 2.5 ppm to 10 ppm, or a salt thereof, and a compound selected from the group consisting of 4-[2,2,3-trimethylcyclopentyl]butanoic acid, 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, and salts thereof.
  2. 2. An orally absorbable or ingestible composition for masking unpleasant odors, characterized in that it comprises an amount for masking unpleasant odors of a masking composition comprising from 2.5 ppm to 10 ppm of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one and at least one of 4-[2,2,3-trimethylcyclopentyl]butanoic acid or 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof, wherein the ratio of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one to 4-[2,2,3-trimethylcyclopentyl]butanoic acid, or salts thereof, is 1:40 to 40:1 and the ratio of The ratio of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one to 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof, is 1:40 to 40:1.
  3. 3. Composition for masking unpleasant odor, characterized in that it consists of 2.5 ppm to 10 ppm of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one and at least one of 4-[2,2,3-trimethylcyclopentyl]butanoic acid or 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof, wherein the ratio of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one to 4-[2,2,3-trimethylcyclopentyl]butanoic acid, or salts thereof, is 1:40 to 40:1 and the ratio of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one to 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof, is 1:40 to 40:1.
  4. 4. Composition for masking unpleasant odor, according to claim 3, characterized in that it consists of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one and 4-[2,2,3-trimethylcyclopentyl]butanoic acid, or salts thereof.
  5. 5. Composition for masking unpleasant odor, according to claim 3, characterized in that it consists of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one and 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof.
  6. 6. Composition for masking unpleasant odor, according to claim 3, characterized in that it consists of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)propan-1-one, 4-[2,2,3-trimethylcyclopentyl]butanoic acid and 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid, or salts thereof.

Description

[001] The present invention relates to the masking of unpleasant odors or tastes and to compounds and compositions for masking such unpleasant odors or tastes. [002] Many orally digestible or ingestible compositions, meaning anything taken orally, whether by swallowing or spitting out, have unpleasant tastes. These unpleasant tastes may be inherent in the composition itself, or they may be the result of a specific additive. Examples of compositions that have an unpleasant taste include coffee, soy milk, and soy yogurt. In the case of additives, specific examples are artificial sweeteners, which have been used in such compositions as a substitute for sugar and corn syrup due to dietary or health reasons. These compounds, examples of which include saccharin, acesulfame K, and aspartame, are considerably sweeter than sugar, and thus can be used in small quantities, replacing a considerably larger amount of sugar. However, it has been observed that, although the predominant taste sensation of these compounds is sweetness, they often additionally impart an undesirable off-flavor, often of a bitter or metallic quality, something absent in sugar and corn syrup. These unpleasant tastes limit the acceptance of compositions that include these compounds, even though they are much healthier. [003] It has been proposed to add compounds that mask such unpleasant tastes. A typical example of such a compound can be found in United States Application No. 2010/227039. [004] It has now been found that another compound has excellent masking qualities for a wide range of unpleasant tastes or odors. A method is therefore provided for masking an unpleasant odor in an orally digestible or ingestible composition, which comprises adding an amount of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)-propan-1-one or a salt thereof for masking unpleasant odors. [005] An orally digestible or orally ingestible composition comprising a proportion of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)-propan-1-one or a salt thereof is also provided for masking unpleasant odors. [006] 1-(2-Hydroxyphenyl)-3-(pyridin-4-yl)-propan-1-one (hereinafter referred to as "Compound 1") is described in U.S. Published Application No. 2010/272656. In that publication, the compound is described as an effective sweetness enhancer. It is a surprising aspect of the present description that the same compound can provide an unpleasant odor or taste masking effect at a concentration much lower than the concentration at which it is perceived as sweet. The minimum level at which the sweetness-enhancing effect of Compound 1 can be detected is 35 ppm, but the unpleasant odor or taste masking effect of the masker can be as low as 2.5 ppm. A practical maximum for unpleasant odor masking is 10 ppm. [007] In another embodiment, the odor-masking effect of Compound 1 can be further enhanced by combining certain other compounds with Compound 1. The description, therefore, also provides a method for masking an unpleasant odor in an orally digestible or orally ingestible composition, which comprises adding an amount of an unpleasant odor-masking composition consisting of 1-(2-hydroxyphenyl)-3-(pyridin-4-yl)-propan-1-one or a salt thereof and at least one of 4-[2,2,3-trimethylcyclopentyl]butanoic acid or 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid or salts thereof. [008] 4-[2,2,3-trimethylcyclopentyl]butanoic acid and 2-[(3-ethyl-4,8-dimethyl-2-oxo-2H-chromen-7-yl)oxy]propanoic acid (hereinafter, respectively, "Compound 2" and "Compound 3") are described in U.S. Patent Publications U.S. 2010/0284944 and U.S. 2010/0227039, respectively. [009] Suitable salts of Compounds 1, 2, or 3 may include, but are not limited to, at least one of K+, NH4+, Na+, Ca2+, Mg2+, Al3+, Zn2+, hydrochloride or hydrobromide salt. Typical ratios of the compounds in masking compositions are now given. These ratios are given only as a general indication and are not intended to be in any way limiting. A person skilled in the art may create desirable effects by working outside of these proportions. [010] Compound 1:Compound 2 ratio: 1:40 to 40:1, in particular 1:20 to 20:1, more particularly 1:7 to 6:1. [011] Compound 1 to Compound 3 ratio: 1:40 to 40:1, in particular 1:20 to 20:1, more particularly 1:7 to 3:1. [012] Compound 1 and the masking composition may be used in a wide variety of products that are receivable and capable of being ingested orally. Non-limiting examples of such products include: [013] Consumer products, including but not limited to all food products, food additives, nutraceutical products, pharmaceutical products and any product placed in the mouth, including chewing gum, oral care products and oral hygiene products, including but not limited to the same, cereal products, rice products, tapioca products, sago products, bakery products, biscuit products, pastry products, bread products, confectionery products, dessert products, gums, chewing gum, mouthwash, dental floss, flavored or flavor