# US 9,872,514 B2 · Compounds, compositions, and methods for reducing or eliminating bitter taste

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- Number: US 9,872,514 B2
- Document ID: US9872514B2
- Status: Granted
- Kind: B2
- Application number: 15/178,149
- Filed: 2016-06-09
- Published: 2017-01-05
- Granted: 2018-01-23
- Earliest claimed: 2010-04-15
- Assignees: Chromocell Corporation
- Applicants: Chromocell Corporation; Kraft Foods Group Brands LLC
- Inventors: Kambiz Shekdar; Daniel Lavery; Joseph Gunnet; Jessica Langer; Jane V. Leland; David Hayashi; Peter H. Brown; Louise Slade; William P. Jones
- Web page: https://patentgrep.com/patent/US9872514B2

## CPC

- A23L 27/86: {Addition of bitterness inhibitors}
- A23L 27/16: Onions
- A23L 27/2024: {having oxygen as the only hetero atom}
- A23L 27/203: {Alicyclic compounds}
- A23L 27/204: {Aromatic compounds}
- A23L 27/2052: {having oxygen or sulfur as the only hetero atoms}
- A61K 47/02: Inorganic compounds
- A61K 47/06: Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K 47/08: containing oxygen, {e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- C07C 63/06: Benzoic acid
- C07C 69/78: Benzoic acid esters
- C07D 311/20: hydrogenated in the hetero ring
- C07D 311/22: with oxygen or sulfur atoms directly attached in position 4
- C07D 311/72: 3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

The present invention provides edible compositions comprising a compound of the present invention, food products comprising such edible compositions and methods of preparing such food products. The present invention also provides methods of reducing the amount of NaCl in a food product, methods of reducing the sodium intake in a diet, and methods of reducing bitter taste in a food product.

## Claims

### Claim 1

A composition comprising a bitter tastant selected from KCl and potassium lactate; and a compound according to Formula (I):
or a comestibly or biologically acceptable salt thereof, or an enantiomer or diastereomer thereof,
wherein, as valence and stability permit:
R1 is absent or is selected from the group consisting of hydrogen, hydroxyl, C1-3alkoxy, and C1-3acyloxy;
R2 is selected from the group consisting of hydrogen, C1-3alkyl, C2-3alkenyl, and C2-3alkynyl;
R3 is selected from the group consisting of hydrogen and C1-3alkoxy;
R4 is selected from the group consisting of hydroxyl, C1-3alkoxy, and C1-3acyloxy;
m is 1;
n is 0;
p is 1; and
t is 1;
wherein all dotted bonds indicate optional carbon-carbon double bonds; and
wherein the composition is edible and the bitter taste due to KCl or potassium lactate is reduced.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein said compound is Compound 41 and having the structure:
or comestibly or biologically acceptable salts thereof, or enantiomers or diastereomers thereof.

### Claim 3 (depends on 1, 2)

The composition of claim 1 or 2, wherein the composition further comprises one or more component selected from the group consisting of: NaCl and sodium lactate.

### Claim 4 (depends on 1, 2)

A food product comprising the composition of any one of claim 1 or 2.

### Claim 5 (depends on 1)

A method of preparing an edible composition comprising KCl or potassium lactate, said method comprising:
(a) providing a comestibly acceptable carrier; and
(b) adding to said comestibly acceptable carrier a compound according to Formula (I) as defined in claim 1, or combinations thereof.

### Claim 6 (depends on 5)

The method according to claim 5, wherein the edible composition further comprises one or more component selected from NaCl and sodium lactate.

### Claim 7 (depends on 1)

A method of reducing the amount of sodium salt in an edible composition comprising:
(a) replacing an amount of sodium salt used in preparing said edible composition with an amount of potassium salt; and
(b) incorporating into the edible composition an effective amount of a compound according to Formula (I) as defined in claim 1, or combinations thereof, to produce an edible composition with reduced sodium salt.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the amount of compound incorporated into the edible composition is sufficient to permit replacement of the amount of 100% of the sodium salt in the edible composition.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the edible composition with reduced sodium salt maintains a salty flavor.

### Claim 10 (depends on 7)

The method according to claim 7, wherein the edible composition with reduced sodium salt has the same shelf life as an edible composition comprising the full amount sodium salt.

### Claim 11 (depends on 5, 7)

The method according to any one of claim 5 or 7, wherein the edible composition is selected from the group consisting of a food product, a consumer product, and a pharmaceutical composition.

### Claim 12 (depends on 7)

The method according to claim 7, wherein the sodium salt is selected from NaCl and sodium lactate, or a combination thereof, and the potassium salt is selected from KCl and potassium lactate, or a combination thereof.

### Claim 13 (depends on 7)

The method according to claim 7, wherein the edible composition with reduced sodium salt has the same shelf life as an edible composition comprising the full amount sodium salt and further wherein the sodium salt is selected from NaCl and sodium lactate, or a combination thereof, and the potassium salt is selected from KCl and potassium lactate, or a combination thereof.

### Claim 14 (depends on 7)

The method according to claim 7, wherein the amount of compound incorporated into the edible composition is sufficient to permit replacement of the amount of 25% of the sodium salt in the edible composition.

### Claim 15 (depends on 7)

The method according to claim 7, wherein the amount of compound incorporated into the edible composition is sufficient to permit replacement of the amount of 50% of the sodium salt in the edible composition.

### Claim 16 (depends on 7)

The method according to claim 7, wherein the amount of compound incorporated into the edible composition is sufficient to permit replacement of the amount of 75% of the sodium salt in the edible composition.