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Compounds, compositions and methods for modulating sweet taste

A composition and compound technology, applied in organic chemistry, food science, etc., can solve problems such as slow sweetness and long-lasting sweetness

Active Publication Date: 2020-12-11
CHROMOCELL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Non-caloric artificial to reduce the level of sweeteners such as caloric and non-caloric sweeteners in foods due to time and / or flavor issues such as slow onset of sweetness, lingering sweetness, bitterness, metallic or licorice and use of natural high-potency sweeteners is limited

Method used

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  • Compounds, compositions and methods for modulating sweet taste
  • Compounds, compositions and methods for modulating sweet taste
  • Compounds, compositions and methods for modulating sweet taste

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0396] Preparation of Compounds of the Invention

[0397] In one embodiment, Compound 1 is prepared by the multi-step sequence described below. Those skilled in the art will readily be able to adapt the described conditions for the synthesis of any compound of formula (I).

[0398] 1: Preparation of 5-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methylchroman-2-one

[0399]

[0400] In a 250 mL flask at room temperature, orcinol A (12.4 g, 100.0 mmol) and ferulic acid B (19.4 g, 100.0 mmol) were suspended in 1,4-bis in alkane (100 mL). Concentrated sulfuric acid (98%, 5 mL) was added slowly for 15 minutes. The suspension was heated to 110°C overnight. The dark hot solution was poured into ice water and extracted twice with ethyl acetate / ether (2:1). The combined organic phases were dried over sodium sulfate and evaporated under vacuum to give a solid which was purified with a 330 g column with 0% to 40% ethyl acetate in hexanes to obtain 23.6 g of the two regioisomers Mi...

Embodiment 1

[0408] Example 1: 2 mandatory options for selection

[0409] Effect of Test Compounds on the Perception of Sweetness in High Fructose Corn Syrup (HFCS)

[0410] 2 alternative forced selection methods (2AFC)

[0411] Two alternative forced choice "sip and spit" methods (2AFC) were used to evaluate the effect of test compounds on the perception of sweetness of aqueous solutions of sweeteners in humans.

[0412] Preparation of samples for sensory taste test:

[0413] An aqueous sweetener solution was prepared by adding sucrose equivalent (SE) high fructose corn syrup (HFCS) (by weight) to water to achieve the desired concentration. The pH of the aqueous solution ranges from 2.5 to 7. Compounds were first prepared as 500-fold concentrated stock solutions in 100% ethanol. These concentrated stock solutions were then added to the aqueous sweetener solution to yield a final ethanol concentration of 0.2%. Control (positive and negative) samples were also normalized to 0.2% ...

Embodiment 2

[0421] Example 2: Intrinsic Sweetness

[0422] Intrinsic Sweetness Evaluation

[0423] Preparation of samples for taste testing

[0424] Aqueous sweetener solutions were prepared by adding HFCS (by weight) equivalent amounts of sucrose to water to achieve the desired concentration. The pH of the aqueous solution ranges from 2.5 to 7.

[0425] Compounds were first prepared as 500-fold concentrated stock solutions in 100% ethanol. These concentrated stock solutions were then added to the aqueous sweetener solution to yield a final ethanol concentration of 0.2%. Control (positive and negative) samples were also normalized to 0.2% ethanol. This level of ethanol was not found to contribute to any perceived sweetness.

[0426] Sensory method: Assessing intrinsic sweetness using the 2AFC method

[0427] The intrinsic effect of test compounds in aqueous solution on sweet taste perception in humans was evaluated using the 2AFC method. The test was a double-blind and randomiz...

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Abstract

The present disclosure provides edible compositions comprising a sweet taste modulator or bitter taste blocker of the present disclosure, food products comprising such edible compositions and methods of preparing such food products. The present disclosure also provides methods of reducing the amount of sugar in a food product, methods of reducing the caloric intake in a diet, and methods of enhancing sweet taste or blocking a bitter taste in a food product.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Application 62 / 102,790, filed January 13, 2015, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present disclosure relates to flavoring agents in edible compositions. Background technique [0004] Whether due to taste preferences, lifestyle reasons or for certain individuals for health-related purposes (diabetics), there is a growing demand in the world for a wider range of options available to reduce the sugar content of foods and beverages. Therefore, health benefits associated with reducing the sugar content of foods and beverages are desirable. Non-caloric artificial to reduce the level of sweeteners such as caloric and non-caloric sweeteners in foods due to time and / or flavor issues such as slow onset of sweetness, lingering sweetness, bitterness, metallic or licorice And the use of natural high-potenc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/58
CPCA23L27/2052A23L27/30A23L27/84A23L27/86A23L27/88A23L29/30A23L29/35C07D311/20
Inventor 罗志勇凯文·柯伦周昊斯图尔特·海登珀维·沙阿
Owner CHROMOCELL CORP