IP Library › Granted Patent US 8,409,649
Granted Patent B2
US 8,409,649 · App. 12/593,114 · Granted Apr 2, 2013

Off-note blocking sensory organic compounds

Inventors: Ioana Maria Ungureanu (Cincinnati, OH); Nicole Erna Irene Brune (San Diego, CA); Jay Patrick Slack (Loveland, OH); Kimberley Gray (Loveland, OH); Christopher Todd Simons (Wyoming, OH); Jenny Ellen Evans Pennimpede (Cincinnati, OH)
Assignee: Givaudan S.A.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,409,649
App. No.
12/593,114
Granted
Apr 2, 2013
Kind
B2
Abstract

Disclosed are compounds that block off-notes in consumables and methods of blocking off-notes in consumables including off-notes provided by artificial sweeteners including aspartame, saccharin, acesulfame K (Acesulfame potassium), sucralose and cyclamate; and including stevioside, swingle extract, glyccerhizin, perillartine, naringin dihydrochalcone, neohesperidine dihydrochalcone, mogroside V, rubusoside, rubus extract, and rebaudioside A.

Claims (14)

1. An off-note blocking compound, wherein the compound is 4-(2,2,3-trimethylcyclopentyl)butanoic acid.

2. A flavor composition comprising an off-note providing consumable ingredient and one or more off-note blocking compounds selected from 4-(2,2,3-trimethylcyclopentyl)butanoic acid, 4-(2,2,6-trimethylcyclohexyl)butanoic acid, 3-(2,2,6-trimethylcyclohexyl)propanoic acid, 2-(3,4-dimethylcyclohexyl)acetic acid, 2-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)butanoic acid, 1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropanecarboxylic acid; (E)-3-(1-(2,2,3-trimethylcyclopent-3-enyl)cyclopropyl)acrylic acid, (E)-4-(2,2,3-trimethylcyclohex-3-enyl)but-2-enoic acid, (E)-4-(2,2,3-trimethylcyclopentyl)but-3-enoic acid, (E)-4-(2,2,3-trimethylcyclopentyl)but-2-enoic acid, 1-methyl-2-(1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropanecarboxylic acid, 2,2-dimethyl-4-(2,2,3-trimethylcyclopentyl)butanoic acid, 2-((1,4-dimethylbicyclo[3.1.0]hexan-2-yl)methyl)-1-methylcyclopropanecarboxylic acid, 2-(1-((1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropyl)propanoic acid, 2-(1-((1-methylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)acetic acid, 3,3-dimethyl-4-(2,2,3-trimethylcyclopentyl)butanoic acid, and 4-(1-methylbicyclo[3.1.0]hexan-2-yl)butanoic acid, (E)-1-(2-(1-methylbicyclo[3.1.0]hexan-2-yl)vinyl)cyclopropanecarboxylic acid, (E)-1-(2-(7-methylspiro[2.4]heptan-4-yl)vinyl)cyclopropanecarboxylic acid, (E)-4-(1-methylbicyclo[3.1.0]hexan-2-yl)but-3-enoic acid, (E)-4-(7-methylspiro[2.4]hept-6-en-4-yl)but-2-enoic acid, (E)-4-(7-methylspiro[2.4]heptan-4-yl)but-3-enoic acid, (E)-4-(7-methylspiro[2.4]heptan-4-yl)but-2-enoic acid, (E)-4-(8-methylspiro[2.5]oct-7-en-4-yl)but-2-enoic acid, 1-(2-(7-methylspiro[2.4]heptan-4-yl)ethyl)cyclopropanecarboxylic acid, 2-((6,7-dimethylspiro[2.4]heptan-4-yl)methyl)-1-methylcyclopropanecarboxylic acid, 2-(1-((1,4-dimethylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)propanoic acid, 2-(1-((1-methylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)acetic acid, 2-(1-((7-methylspiro[2.4]heptan-4-yl)methyl)cyclopropyl)acetic acid, and 4-(7-methylspiro[2.4]heptan-4-yl)butanoic acid.

3. A consumable comprising

a) one or more ingredient in a concentration sufficient to provide an off-note, and

b) one or more off-note blocking compounds selected from 4-(2,2,3-trimethylcyclopentyl)butanoic acid, 4-(2,2,6-trimethylcyclohexyl)butanoic acid, 3-(2,2,6-trimethylcyclopentyl)butanoic acid, 2-(3,4-dimethylcyclohexyl)acetic acid, 2-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)butanoic acid, 1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropanecarboxylic acid, (E)-3-(1-(2,2,3-trimethylcyclopent-3-enyl)cyclopropyl)acrylic acid, (E)-4-(2,2,3-trimethylcyclohex-3-enyl)but-2-enoic acid, (E)-4-(2,2,3-trimethylcyclopentyl)but-3-enoic acid, (E)-4-(2,2,3-trimethylcyclopentyl)but-2-enoic acid, 1-methyl-2-(1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropanecarboxylic acid, 2,2-dimethyl-4-(2,2,3-trimethylcyclopentyl)butanoic acid, 2-((1,4-dimethylbicyclo[3.1.0]hexan-2-yl)methyl)-1-methylcyclopropanecarboxylic acid, 2-(1-((1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropyl)propanoic acid, 2-(1-((1-methylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)acetic acid, 3,3-dimethyl-4-(2,2,3-trimethylcyclopentyl)butanoic acid, and 4-(1-methylbicyclo[3.1.0]hexan-2-yl)butanoic acid, (E)-1-(2-(1-methylbicyclo[3.1.0]hexan-2-yl)vinyl)cyclopropanecarboxylic acid, (E)-1-(2-(7-methylspiro[2.4]heptan-4-yl)vinyl)cyclopropanecarboxylic acid, (E)-4-(1-methylbicyclo[3.1.0]hexan-2-1 but-3-enoic acid (E)-4-(7-methylspiro[2.4]hept-6-en-4-yl)but-2-enoic acid, (E)-4-(7-methylspiro[2.4]heptan-4-yl)but-3-enoic acid, (E)-4-(7-methylspiro[2.4]heptan-4-yl)but-2-enoic acid, (E)-4-(8-methylspiro[2.5]oct-7-en-4-yl)but-2-enoic acid, 1-(2-(7-methylspiro[2.4]heptan-4-yl)ethyl)cyclopropanecarboxylic acid, 2-((6,7-dimethylspiro[2.4]heptan-4-yl)methyl)-1-methylcyclopropanecarboxylic acid, 2-(1-((1,4-dimethylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)propanoic acid, 2-(1-((1-methylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)acetic acid, 2-(1-((7-methylspiro[2.4]heptan-4-yl)methyl)cyclopropyl)acetic acid, and 4-(7-methylspiro[2.4]heptan-4-yl)butanoic acid.

4. The consumable of claim 3 , wherein the one or more off-note providing ingredient is selected from the group consisting of sweetener, artificial sweetener, beverage, chewing gum, nutraceutical, and pharmaceutical.

5. The consumable of claim 3 , wherein the one or more off-note providing ingredient comprises an artificial sweetener selected from the group consisting of aspartame, Acesulfame K, saccharin, sucralose, sodium cyclamate and mixtures thereof.

6. The consumable of claim 3 , wherein the one or more off-note providing ingredient comprises a sweetener selected from the group consisting of stevioside, swingle extract, glycyrrhizin, perillartine, naringin dihydrochalcone, neohesperidine dihydrochalcone, mogroside V, rubusoside, rubus extract, rebaudioside A and mixtures thereof.

7. The consumable of claim 3 , wherein the one or more off-note providing ingredient comprises a consumable selected from the group consisting of cocoa; coffee; caffeine; theobromine; diketopiperazines; vitamins; amino acids; vitamin B; casein; soy protein; ibuprofen; salicylic acid; glucoronolactone; acetaminophen; dextromethorphan; naringin; taurine; macrolide; bioxin; erythromycin; paracetamol; acetylsalicylic acid; cimetidine; ranitidine; amoxicillin; cephalosporins; quassia; propylene glycol; triacetin; potassium; zinc; loperamide; limonin; flavonoids; isoflavones; genistein; diadzein; polyphenol; catechin; epicatechin; mint oil; D-menthol; hydrolysed vegetable protein; bitter peptides; preservatives; benzoic acid; potassium sorbate; polysorbate 80; sodium lactate; potassium lactate; sodium benzoate; citric acid; quinine; urea contained in chewing gums; essential oils; thyme; sage; basil; mint; Maillard reaction products; cyclic amines made from pyrrolidine/glucose, alanine/xylose, proline/sucrose or alanine/xylose; beer; hops; humulone; trans-isohumulone; lupulone; hulupone; and mixtures thereof.

8. A method of blocking off-notes in consumables comprising: admixing with the consumable (a) one or more off-note providing ingredient in a concentration sufficient to provide an off-note, and (b) one or more off-note blocking compound selected from of 4-(2,2,3-trimethylcyclopentyl)butanoic acid, 4-(2,2,6-trimethylcyclohexyl)butanoic acid, 3-(2,2,6-trimethylcyclohexyl)propanoic acid, 2-(3,4-dimethylcyclohexyl)acetic acid, 2-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)butanoic acid, 1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropanecarboxylic acid, (E)-3-(1-(2,2,3-trimethylcyclopent-3-enyl)cyclopropyl)acrylic acid, (E)-4-(2,2,3-trimethylcyclohex-3-enyl)but-2-enoic acid, (E)-4-(2,2,3-trimethylcyclopentyl)but-3-enoic acid, (E)-4-(2,2,3-trimethylcyclopentyl)but-2-enoic acid, 1-methyl-2-(1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropanecarboxylic acid, 2,2-dimethyl-4-(2,2,3-trimethylcyclopentyl)butanoic acid, 2-((1,4-dimethylbicyclo[3.1.0]hexan-2-yl)methyl-1-methylcyclopropanecarboxylic acid, 2-(1-((1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropyl)propanoic acid, 2-(1-((1-methylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)acetic acid, 3,3-dimethyl-4-(2,2,3-trimethylcyclopentyl)butanoic acid, and 4-(1-methylbicyclo[3.1.0]hexan-2-yl)butanoic acid, (E)-1-(2-(1-methylbicyclo[3.1.0]hexan-2-yl)vinyl)cyclopropanecarboxylic acid, (E)-1-(2-(7-methylspiro[2.4]heptan-4-yl)vinyl)cyclopropanecarboxylic acid, (E)-4-(1-methylbicyclo[3.1.0]hexan-2-1 but-3-enoic acid (E)-4-(7-methylspiro[2.4]hept-6-en-4-yl)but-2-enoic acid, (E)-4-(7-methylspiro[2.4]heptan-4-yl)but-3-enoic acid, (E)-4-(7-methylspiro[2.4]heptan-4-yl)but-2-enoic acid, (E)-4-(8-methylspiro[2.5]oct-7-en-4-yl)but-2-enoic acid, 1-(2-(7-methylspiro[2.4]heptan-4-yl)ethyl)cyclopropanecarboxylic acid, 2-((6,7-dimethylspiro[2.4]heptan-4-yl)methyl)-1-methylcyclopropanecarboxylic acid, 2-(1-((1,4-dimethylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)propanoic acid, 2-(1-((1-methylbicyclo[3.1.0]hexan-2-yl)methyl)cyclopropyl)acetic acid, 2-(1-((7-methylspiro[2.4]heptan-4-yl)methyl)cyclopropyl)acetic acid, and 4-(7-methylspiro[2.4]heptan-4-yl)butanoic acid.

9. The method of claim 8 , wherein the one or more off-note providing ingredient is selected from the group consisting of sweetener, artificial sweetener, beverage, chewing gum, nutraceutical, and pharmaceutical.

10. The method of claim 8 , wherein the one or more off-note providing ingredient comprises an artificial sweetener selected from the group consisting of aspartame, acesulfame K, saccharin, sucralose, sodium cyclamate and mixtures thererof.

11. The method of claim 8 , wherein the one or more off-note providing ingredient comprises a sweetener selected from the group consisting of including stevioside, swingle extract, glycyrrhizin, perillartine, naringin dihydrochalcone, neohesperidine dihydrochalcone, mogroside V, rubusoside, rubus extract, rebaudioside A and mixtures thereof.

12. The method of claim 8 , wherein the one or more off-note providing ingredient comprises a consumable selected from the group consisting of cocoa; coffee; caffeine; theobromine; diketopiperazines; vitamins; amino acids; vitamin B; casein; soy protein; ibuprofen; salicylic acid; glucoronolactone; acetaminophen; dextromethorphan; naringin; taurine; macrolide; bioxin; erythromycin; paracetamol; acetylsalicyclic acid; cimetidine; ranitidine; amoxicillin; cephalosporins; quassia; propylene glycol; triacetin; potassium; zinc; loperamide; limonin; flavonoids; isoflavones; genistein; diadzein; polyphenol; catechin; epicatechin; mint oil; D-menthol; hydrolysed vegetable protein; bitter peptides; preservatives; benzoic acid; potassium sorbate; polysorbate 80; sodium lactate; potassium lactate; sodium benzoate; citric acid; quinine; urea contained in chewing gums; essential oils; thyme; sage; basil; mint; Maillard reaction products; cyclic amines made from pyrrolidine/glucose, alanine/xylose, proline/sucrose or alanine/xylose; beer; hops; humulone; trans-isohumulone; lupulone; hulupone and mixtures thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2009
From: UNGUREANU, IOANA MARIA; IRENE BRUNE, NICOLE ERNA; SLACK, JAY PATRICK; GRAY, KIMBERLEY; SIMONS, CHRISTOPHER TODD; EVANS PENNIMPEDE, JENNY ELLEN
To: GIVAUDAN SA
Reel/Frame 023291/0216 →
Continuity (3)
Provisional Application 60909143 · Mar 30, 2007
Provisional Application 60962515 · Jul 30, 2007
Related Publication 20100284944A1 · Nov 11, 2010