Homovanillinic acid ester, in particular for creating a warm and/or pungent sensation

Patent metadata

Field	Value
Publication number	US-11535584-B2
Application number	US-202017077133-A
Country	US
Kind code	B2
Filing date	Oct 22, 2020
Priority date	Apr 16, 2014
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

Compounds of formula (I) and novel uses of compounds of formula (I), such as for flavour compositions. New preparations and new methods using compounds of formula (I).

First claim

The invention claimed is:

1. A method for imparting a warm and/or pungent taste sensation, the method comprising:
adding 5 to 1,000 mg/kg of one or more compounds of formula (I), or physiologically acceptable salt thereof, to a preparation that comes into contact with an oral cavity, wherein the compounds of formula (I) are represented by the following structure:

wherein

(i) R 1 and R 2 represent, independently of each other, a hydrogen atom or an alkyl residue with 1-2 carbon atoms, and
R 3 and R 4 represent, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue; or

(ii) R 1 and R 3 along with the carbon atoms linking them form a cyclohexyl ring,
R 2 represents a hydrogen atom or an alkyl residue with 1-2 carbon atoms,
R 4 represents a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms, a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or a linear or branched alkenyl residue with 2 to 4 carbon atoms or an alkenylphenyl residue or a phenylalkenyl residue,
wherein the one or more compounds in accordance with formula I being one or several different compounds of formula (I), and/or physiologically acceptable salts thereof, where the phenolic hydroxy group in formula (I) is deprotonated, respectively.

2. The method of claim 1 , wherein one or more of the compounds of formula (I), independently of each other, have R 1 and R 2 being, independently of each other, a hydrogen atom or methyl group, R 3 and R 4 being, independently of each other, a hydrogen atom or a linear or branched alkyl residue with 1 to 5 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue.

3. The method of claim 1 , wherein one or more of the compounds of formula (I), independently of each other, are represented by the following structure for Formula (Ia)

wherein R 2 is a hydrogen atom and R 4 is 2-propyl.

4. The method of claim 1 , wherein one or more of the compounds of formula (I), independently of each other, have:
R 1 and R 2 being a hydrogen atom, respectively,
R 3 being a hydrogen atom or a linear or branched alkyl residue with 1 to 4 carbon atoms or a phenyl residue, an alkylphenyl residue or a phenylalkyl residue or an alkenylphenyl residue or a phenylalkenyl residue, R 4 being a hydrogen atom.

5. The method of claim 1 , wherein the one or more compounds of formula (I) are selected from:

6. The method of claim 1 , wherein the one or more compounds of formula (I) are selected from:

7. The method of claim 1 , wherein the one or more compounds of formula (I) includes:
1 ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17)

8. The method of claim 1 comprising adding 5 to 500 mg/kg of the one or more compounds of formula (I), or physiologically acceptable salt thereof.

9. A method for imparting a warm and/or pungent taste sensation to a preparation that comes into contact with an oral cavity, the method comprising adding 5 to 500 mg/kg of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) to the preparation:

10. A method for imparting a warm and/or pungent taste sensation to a preparation that comes into contact with an oral cavity, the method comprising:
(a) adding 5 to 1,000 mg/kg of ethyl-2-(4-hydroxy-3-methoxyphenyl) acetate (17) to the preparation:

 and
(b) adding at least one further compound selected from the group consisting of

11. The method of claim 1 , wherein the preparation is not a wine or a wine cocktail.

12. The method of claim 1 , wherein the preparation does not comprise ethanol.

Assignees

• Symrise Ag

Inventors

• Backes Michael
• Ley Jakob Peter
• Degenhardt Andreas
• Paetz Susanne
• Reichelt Katharina
• Riess Thomas
• Klose Bettina
• Hentschel Fabia

Classifications

• A23L27/204 Primary

  Aromatic compounds · CPC title

• C07C69/734 Primary

  Ethers · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• A23L27/2052

  having oxygen or sulfur as the only hetero atoms · CPC title

• A23B4/06

  Freezing; Subsequent thawing; Cooling · CPC title