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Heat-processed products having altered monomer profiles and processes for controlling the epimerization of (-)-epicatechin and (+)-catechin in the products

A technology of epimerization of epicatechin, applied in the field of new products, can solve the problems of not explaining the increase of pH or slowing down the rate of epimerization of epicatechin, and not explaining the effect of pH

Inactive Publication Date: 2008-07-09
MARS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Reports of epimerization of (-)-epicatechin and (+)-catechin at the C-2 position do not address the role of pH in the kinetics of this reaction, nor do they suggest that pH increases or slows Effect of epicatechin on the rate of epimerization of catechin

Method used

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  • Heat-processed products having altered monomer profiles and processes for controlling the epimerization of (-)-epicatechin and (+)-catechin in the products
  • Heat-processed products having altered monomer profiles and processes for controlling the epimerization of (-)-epicatechin and (+)-catechin in the products
  • Heat-processed products having altered monomer profiles and processes for controlling the epimerization of (-)-epicatechin and (+)-catechin in the products

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0062] The following procedure was used for the preparation and testing of the articles.

[0063] sample preparation

[0064] Normal Phase Chromatography—HPLC / MS Analysis (Adamson et al. method)

Embodiment 8

[0065] For Example 8, the published normal phase HPLC method of Adamson et al. (J. Agric. Food Chem. 1999, 47 pp. 4184-4186) was used.

[0066] The conditions are as follows:

[0067] a) column

[0068] Phenomenex Lichrosphere Silica

[0069] Size: 25cm×4.6mm

[0070] Particle size: 5 microns

[0071] Pore ​​diameter: 100 Angstroms

[0072] b) mobile phase

[0073] A. Dichloromethane

[0074] B. Methanol

[0075] C. Water: acetic acid (1:1)

[0076] Gradient condition:

[0077] Starting: 82%A / 14%B / 4%C

[0078] Time = 30 minutes 67.6%A / 28.4%B / 4%C

[0079] Time = 50 minutes 53.2%A / 42.8%B / 4%C

[0080] Time = 51 minutes 10%A / 86%B / 4%C

[0081] Time = 56 minutes 82%A / 14%B / 4%C

[0082] Rebalance - 7 minutes

[0083] c) Flow rate: 1.0ml / min

[0084] d) Column temperature: 37°C

[0085] e) Injection volume: 5.0ml

[0086] f) Detection: fluorescence; excitation wavelength 276nm; emission wavelength 316nm

[0087] Normal Phase Chromatography: Diol Method

[0088] For t...

Embodiment 1

[0099] Example 1 : Put a 1 mg / ml solution of (-)-epicatechin (purchased from Sigma Aldrich) in a buffer solution (sodium phosphate at pH 6 and 7, sodium citrate at pH 4) in a tubular reactor , the epimerization was carried out under a controlled atmosphere. Figure 1 shows a schematic diagram of the reactor used.

[0100] Epimerization was carried out under nitrogen atmosphere to avoid the loss of (-)-epicatechin by oxidation. Nitrogen was used to create pressure inside the feed tank to push the solution into the tubular reactor, which was immersed in an oil bath to heat to the desired temperature. The thin design of the tubular reactor facilitated rapid heat transfer, ensuring that (-)-epicatechin was heated to the desired temperature almost immediately. Aliquots of 5 ml were collected during the reaction, kept on ice and quenched with 10N HCl to prevent oxidation during component analysis.

[0101] The composition of the collected mixed (-)-epicatechin / (-)-catechin sample...

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Abstract

A method for controlling the isomerization of (-)-epicatechin to (-)-catechin in an epicatechin-containing product, preferably an edible product, which method comprises the step of heating the product at a temperature of up to about 190 DEG C. and at a pH of up to about 8. A method for controlling the isomerization of (+)-catechin to (+)-epicatechin in a catechin-containing product, preferably an edible product, which method comprises the step of heating the product, at a temperature of up to about 190 DEG C. and at a pH of up to about 8. Preferably, the temperature is from about 72 DEG C. to about 125 DEG C., the pH is from about 4 to about 7, and the time is at least about 15 seconds. Under either method, the isomerization may be carried out in an open food processor in a reduced oxygen atmosphere or in a closed food processor. The edible product may be pasteurized, boiled or sterilized during the isomerization. The isomerization is minimized by lowering the heating temperature, by lowering the pH, and / or by lowering the heating time. Conversely, the isomerization is maximized by increasing the heating temperature, by increasing the pH, and / or by increasing the heating time. The edible product may contain or be a fruit product, a vegetable product, a cereal product, a bean product, a nut product, or a spice product.

Description

[0001] Cross reference to related applications [0002] This PCT application is U.S. Patent Application Serial No. 11 / 170,593, "Controlling the Isomerization of (-)-Epicatechin and (+)-Catechin in Edible Food Products" filed on June 29, 2005 The method of " part of the continuation of the application. field of invention [0003] The present invention relates to novel preparations, in particular cocoa preparations, and the control of (-)-epicatechin versus (-)-catechin and (+)-catechin versus (+)-epicatechin in edible preparations Method of epimerization of acids. Background of the invention [0004] It is known that (+)-catechin and (-)-epicatechin epimerize at the 2-position in hot aqueous solution. The epimers produced are (+)-epicatechin and (-)-catechin. [0005] It is also known that the formation of epimers of tea catechins, which are essentially gallate monomers, is the result of heat treatment. Reports of epimerization of (-)-epicatechin and (+)-catechin at the C...

Claims

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Application Information

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IPC IPC(8): C07D311/00A23L1/28A23L5/10
CPCA23B7/005A23G1/30A23B9/02A23G1/0016C07D311/62A23L1/3002A23L33/105
Inventor J·F·小哈默斯通V·阿夸罗内
Owner MARS INC
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