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Aromatic amides and ureas and their uses as sweet and/or delicate flavor modifiers, flavouring agents and taste enhancers

A flavoring and sweetening technology, applied in the fields of savory or sweet flavorings and savory or sweet flavor enhancers, can solve the problems of expensive, difficult separation and purification of natural sources

Inactive Publication Date: 2008-06-18
SENOMYX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the naturally occurring nucleotide compounds inosinic acid (IMP) or guanylic acid (GMP) are known to have a multiplier effect on the savory taste of MSG, but isolating and purifying IMP and GMP from natural sources or synthesizing IMP and GMP is very difficult. Difficult and expensive and therefore of very limited practical use for most commercial needs in food or pharmaceutical compositions

Method used

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  • Aromatic amides and ureas and their uses as sweet and/or delicate flavor modifiers, flavouring agents and taste enhancers
  • Aromatic amides and ureas and their uses as sweet and/or delicate flavor modifiers, flavouring agents and taste enhancers
  • Aromatic amides and ureas and their uses as sweet and/or delicate flavor modifiers, flavouring agents and taste enhancers

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0555] Reaction formula 1c. Preparation of oxalamide

[0556]

[0557] As a general procedure, react an amine with ethyloxalyl chloride in the presence of a tertiary amine in an organic solvent such as dioxane, acetonitrile, tetrahydrofuran, tetrahydropyran, and dimethylformamide at room temperature for 0.5 to 2 hours. The second amine was then added and the suspension was heated at 80°C overnight using an oil bath, or at 160°C for 5 minutes in a microwave reactor. The reaction mixture can be subjected to preparative HPLC, or subjected to aqueous work-up (aqueous work-up), and the crude product can usually be easily purified by recrystallization, flash column chromatography, or other methods well known to those of ordinary skill in the art to give pure ethyl diamide. The yields reported below were not optimized.

[0558] Reaction formula 1d. Preparation of urea

[0559]

[0560] x 1 、X 2 and x 3 Each is independently an alkyl or alkoxy group.

[0561]Scheme 2 des...

Embodiment 1

[0635] N-(hept-4-yl)benzo[d][1,3]dioxol-5-carboxamide

[0636]

[0637] To a solution of heptane-4-amine (8.06 mL, 54 mmol) in triethylamine (15.3 mL, 108 mmol) and dichloromethane (135 mL) was added dropwise dissolved in dichloromethane (135 mL) at 0°C. A solution of benzo[1,3]dioxol-5-carbonyl chloride (10 g, 54 mmol). The reaction mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed sequentially with 1N aqueous HCl, 1N aqueous NaOH, water, brine, and dried (MgSO 4 ) and concentrate. The residue was recrystallized from EtOAc and hexanes to afford 6.9 g of N-(heptyl-4-yl)benzo[d][1,3]dioxol-5-carboxamide (48.3%) as a white solid. 1 H NMR (500MHz, CDCl 3 ): δ0.92(t, 6H), 1.38(m, 6H), 1.53(m, 2H), 4.11(m, 1H), 5.63(m, 1H), 6.01(s, 2H), 7.98(d, 1H), 7.27 (s, d, 2H). MS (M+H, 264).

[0638] The compound activates the EC of hT1R1 / hT1R3 umami taste receptors expressed in HEK293...

Embodiment 2

[0640] N-(2-Methylhept-4-yl)benzo[d][1,3]dioxol-5-carboxamide

[0641]

[0642] Prepared in a similar manner to Example 1 using benzo[d][1,3]dioxol-5-carbonyl chloride and 2-methylheptan-4-amine (Example 2a). 1 H NMR (500MHz, CDCl 3 ): δ0.93(m, 9H), 1.38(m, 5H), 1.53(m, 1H), 1.66(m, 1H), 4.21(m, 1H), 5.61(d, 1H), 6.01(s, 2H), 6.82 (d, 1H), 7.26 (m, 2H). MS (278, M+H).

[0643] a. Preparation of 2-methylheptan-4-amine

[0644] To a solution of 2-methylheptan-4-one (4.24 g, 33.07 mmol) in methanol (60 mL) was added ammonium acetate (25.50 g, 330.71 mmol) and sodium cyanoborohydride (2.08 g, 33.07 mmol). The reaction mixture was stirred at room temperature for about 24 hours. The solvent was removed under reduced pressure, the residue was diluted with water and basified with 15% aqueous NaOH, and extracted with ether. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 3.3 g of 2-methylheptan-4-amine (77%). MS (M+H,...

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Abstract

The present invention relates to aromatic amides and ureas and their use as sweet and / or umami taste improvers, flavoring agents and flavor enhancers. The present disclosure relates to non-naturally occurring amide compounds capable of serving as a savory taste ( "Umami") or sweet taste improvers, savory or sweet flavoring agents and savory or sweet flavor enhancers, which compounds may be used in food, beverages and other edible or orally pharmaceutical preparations or compositions , this compound is optionally used simultaneously or mixed with traditional flavoring agents such as monosodium glutamate or known natural and artificial sweeteners.

Description

[0001] This application claims priority to US Utility Patent Application Serial No. 11 / 051,567, filed February 4, 2005, the entire disclosure of which is incorporated herein by reference. Contents of the invention [0002] The present invention relates to the discovery of flavor modifiers or taste modifiers, such as seasonings or seasonings and flavor enhancers or flavor enhancers, and more particularly, to the discovery of flavor enhancers or taste enhancers for use in foods, beverages and other edible or orally administered pharmaceuticals or compositions. Savory ("umami") improvers or sweet taste improvers, savory or sweet flavors and savory or sweet flavor enhancers. Background technique [0003] Over the centuries, various natural and non-natural compositions and / or compounds have been added to edible (edible) foods, beverages and / or oral pharmaceutical compositions to improve their taste. Although only a few basic types of "taste" have long been known, the biological o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A23L1/226A23L1/231A23L27/20A23L27/00A23L27/26A23L27/30A23L29/00
CPCA23L1/22685A23L1/22664A23L27/205A23L27/2056A23L27/20A23L27/26A23L27/30
Inventor 凯瑟琳·塔奇杜健安德鲁·P·佩特伦齐铭萨沙·阿达米斯基-沃纳唐小清陈情文森特·达尔莫胡索多马尔凯塔·列布尔-林诺娃查德·普利斯特
Owner SENOMYX INC
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