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Sweetness Enhancers, Sweetness Enhanced Sweetener Compositions, Methods for Their Formulation, and Uses

a technology of sweetener composition and enhancer, which is applied in the field of sweetener compositions with enhanced sweetness, can solve the problems of prohibitively high cost of many non-caloric or low-caloric sweeteners, and achieve the effect of enhancing the sweetness of sweetener compositions and enhancing the sweetness of sweetened compositions

Inactive Publication Date: 2008-11-27
THE COCA-COLA CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0005]Generally, this invention addresses the above-described need by providing a sweetness enhancer comprising a sulfamate analogue for enhancing sweetness. In a particular embodiment, the sweetness enhancer comprises a sulfamate having the chemical formula:
[0008]Objects and advantages of the invention will be set forth in part in the following description, or may be obvious from the description, or may be learned through practice of the invention. Unless otherwise defined, all technical and scientific terms and abbreviations used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Although methods and compositions similar or equivalent to those described herein can be used in the practice of the present invention, suitable methods and compositions are described without intending that any such methods and compositions limit the invention herein.

Problems solved by technology

Many non-caloric or low-caloric sweeteners, however, are prohibitively expensive.

Method used

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  • Sweetness Enhancers, Sweetness Enhanced Sweetener Compositions, Methods for Their Formulation, and Uses
  • Sweetness Enhancers, Sweetness Enhanced Sweetener Compositions, Methods for Their Formulation, and Uses
  • Sweetness Enhancers, Sweetness Enhanced Sweetener Compositions, Methods for Their Formulation, and Uses

Examples

Experimental program
Comparison scheme
Effect test

example set a

Synthesis of Sulfamates

[0870]Synthesis of various sulfamates was carried out using the methods described in J Org Chem 1980, 45(26), 5371-73 and ARKIVOC 2003 7, 297-309.

example a1

SODIUM 1H 1,3,5-TRIAZOLYL SULFAMATE

[0871]In a round bottom flask, sulfur trioxide pyridine complex (22 mmol, 3.5 g) was dissolved in 22 mL of dry pyridine and cooled to 0° C. 4-Amino-4-H-]1,2,4-triazole (20.0 mmol, 1.68 g) was dissolved in a minimum amount of pyridine and was added dropwise to the sulfur trioxide pyridine complex under nitrogen. The mixture was removed from the cooling bath and stirred at room temperature overnight. The pH of the reaction mixture was adjusted to approximately 10 with a 2 M aqueous sodium hydroxide and the organic layer was extracted with diethyl ether (3×50 mL) to eliminate unreacted amine. The resultant aqueous layer was concentrated and the sulfamate obtained was crystallized using 90-95% ethanol to obtain an 11.2% yield of the sulfamate.

example a2

SODIUM 1H 1,3-BENZODIAZOL-2-YL SULFAMATE

[0872]Sulfur trioxide pyridine complex (22 mmol, 3.5 gm) was dissolved in dry pyridine (22 mL) and was cooled in an ice-bath to 0° C. 2-Aminobenzimidazole (20.0 mmol, 2.6 g) was dissolved in a minimum amount of pyridine, taken up in a dropping funnel, and slowly added to the sulfur trioxide pyridine complex under nitrogen. The mixture was brought to room temperature and stirred overnight. The reaction was quenched, pH adjusted, and organic layer extracted as described in Example A1. The resultant aqueous layer was concentrated and the sulfamate obtained was crystallized using 95% ethanol to obtain an 11.34% yield of the sulfamate product.

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Abstract

The present invention relates generally to sweetness enhancers capable of enhancing the sweet taste of sweetener compositions and the sweetener compositions produced therefrom. In particular, the present invention relates to sweetener compositions comprising sulfamates capable of enhancing the sweetness of the sweetener composition.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]The present application claims priority under 35 U.S.C. §119(c) to U.S. Provisional Application No. 60 / 939,554, filed on May 22, 2007, the disclosure of which is hereby incorporated by reference in its entirety.FIELD OF THE INVENTION[0002]The present invention relates to sweeteners having enhanced sweetness. In particular, the present invention relates to use of sulfamate analogues as sweetness enhancers and / or taste modulators.BACKGROUND OF THE INVENTION[0003]Although natural caloric sweetener compositions such as sucrose, fructose, and glucose taste good to most consumers, they are caloric. Therefore, alternative non-caloric or low-caloric sweeteners have been used widely as sugar or sucrose substitutes. Many non-caloric or low-caloric sweeteners, however, are prohibitively expensive. Thus, it may be desirable to identify compounds capable of enhancing or increasing the perception of sweetness of such sweeteners. By combining such compo...

Claims

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Application Information

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IPC IPC(8): A23L1/236A23L27/00A23L27/30
CPCA23L1/236A23L1/22091A23L27/88A23L27/30
Inventor PRAKASH, INDRADUBOIS, GRANT E.KING, GEORGE A.UPRETI, MANIKLUCIK, JOSEFSAN MIGUEL, RAFAEL I.
Owner THE COCA-COLA CO
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