Comestible compositions comprising high potency savory flavorants, and processes for producing them

A composition and compound technology, applied in the preparation of food and beverages, the preparation of some umami tastant compounds disclosed in this paper, and the preparation of food seasoning concentrate compositions, which can solve the problem that the compound is not optimal

Inactive Publication Date: 2009-05-06
SENOMYX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] However, when a new chemical entity (chemical entity), such as a new highly potent savory compound, is discovered that is safe for human use, the original laboratory operations that first prepared the compound are critical for producing commercial quantities of the compound. may not be the best way to say
In the prior art, it has not been found that the high-efficiency umami flavor compound N-(2,4-dimethoxybenzyl)-N'-[2-(pyridin-2-yl)ethyl]oxamide and A synthetic procedure for 2-H-benzo[3,4-d]1,3-dioxolan-5-yl-N-(propylbutyl)-formamide has therefore been initiated to develop a suitable, large-capacity Method for large-scale production of the above-mentioned compounds

Method used

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  • Comestible compositions comprising high potency savory flavorants, and processes for producing them
  • Comestible compositions comprising high potency savory flavorants, and processes for producing them
  • Comestible compositions comprising high potency savory flavorants, and processes for producing them

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Experimental program
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preparation example Construction

[0320] The preparation of formula (I) amide compound

[0321] The starting materials for the preparation of various structural subclasses and specific substances of the compounds of the present invention, amide compounds of formula (I) and their synthetic precursors, and methods for preparing the above compounds are disclosed in U.S. Patent Publication Nos. US 2005 / 0084506 A1 and These two patent applications are incorporated herein by reference in US Patent Publication No. US 2006 / 0045953 Al, or as described below.

[0322] resolve resolution

[0323] The following schemes and examples are provided to guide the reader and represent various methods for preparing the amide compounds of this invention. The methods disclosed are for purposes of illustration only and are not limiting, and it will be apparent to those skilled in the art that other methods, many of which are well known, may be used to prepare the amide compounds in various embodiments of the invention. These met...

Embodiment 1

[0500] N-(hept-4-yl)benzo[d][1,3]dioxol-5-carboxamide

[0501]

[0502] To a solution of hept-4-amine (8.06 mL, 54 mmol) in triethylamine (15.3 mL, 108 mmol) and dichloromethane (135 mL) was added dropwise benzo[1,3]dioxole at 0 °C -5-Acyl chloride (10 g, 54 mmol) in dichloromethane (135 mL). The reaction mixture was stirred for 1 h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc (ethyl acetate). The organic layer was washed successively with 1N aqueous HCl, 1N aqueous NaOH, water, brine, dried (MgSO4), and concentrated. The residue was recrystallized from EtOAc and hexanes to afford 6.9 g of N-(hept-4-yl)benzo[d][1,3]dioxole-5-carboxamide (48.3% ). 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).

[0503] This compound activates the EC of hT1R1 / hT1R3 umami taste receptors expressed on HEK293 cell line 50 It is 0.2μM, and when...

Embodiment 1-1

[0505] Improvements in the preparation and purification of N-(hept-4-yl)benzo[d][1,3]dioxole-5-carboxamide:

[0506]

[0507] In a clean fume hood, place a 3-neck round bottom flask equipped with a mechanical stirring assembly, addition funnel, thermocouple with display, nitrogen gas inlet, and drying tube in a cooling bath. The flask was also blanketed with nitrogen. 674 g of 4-heptylamine (1 equivalent, 5.85 moles) was added to the flask under nitrogen protection. THF (tetrahydrofuran) (3.37 L) was then added to the flask and the reaction mixture was stirred. Then triethylamine (1184 g, 2 eq, 11.7 mol) was added to the reaction mixture under nitrogen protection, and the reaction mixture was cooled to an internal temperature of -5°C to 0°C.

[0508] Piperonyl chloride (1080 g, 5.85 mol) was dissolved in THF (3.37 L) in a polyethylene jar and stored under nitrogen. Transfer this solution to the addition funnel of the 3-neck flask. This solution was added portionwise to ...

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Abstract

The present invention relates to the use of certain high potency savory (''umami'') taste modifiers, as savory flavoring agents and / or enhancers of monosodium glutamate, for the preparation of foods, beverages, and other comestible compositions, and to processes for preparing food flavorant compositions for use in the preparation of comestible food and drink.

Description

[0001] related application [0002] This application claims the benefit of U.S. Provisional Patent Application Serial No. 60 / 793,844, filed April 21, 2006, and U.S. Provisional Patent Application Serial No. 60 / 847,632, filed September 27, 2006, which The entire disclosure is hereby incorporated by reference. technical field [0003] The invention disclosed herein relates to certain high potency savory ("umami" means "umami" in Japanese) taste modifiers as savory flavoring agents and / or sodium glutamate Use of an enhancer in the preparation of food, beverages and other edible compositions, and relates to a method for the preparation of a food flavor concentrate composition (food flavorant concentrate composition) for the preparation of food and drinks. The present invention also relates to methods of making certain savory tastant compounds disclosed herein. Background of the invention [0004] Various natural and non-natural compositions and / or compounds have been added to...

Claims

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Application Information

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IPC IPC(8): A23L1/22A23L27/00
Inventor 朗蒂·西格马拉陈情文森特·达莫休索多阿伦·R·迪安
Owner SENOMYX INC
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