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Compositions and methods for improving rebaudioside x solubility

a technology of rebaudioside and solubility, which is applied in the field of crystallized forms and amorphous rebaudiosides, can solve the problems of poor aqueous solubility and dissolution qualities of rebaudioside x obtained from stevia rebaudiana, and achieve the effect of improving solubility properties

Inactive Publication Date: 2014-06-19
THE COCA-COLA CO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes a new form of Rebaudioside X that has improved solubility in water compared to other forms. This new form has a higher aqueous solubility of 0.3% or greater. The patent also explains how to create Rebaudioside X complexes that have even better solubility. These complexes can be made by certain methods described in the patent. This information can be useful for creating products that contain Rebaudioside X, where the solubility of the ingredient is important.

Problems solved by technology

Rebaudioside X obtained from Stevia rebaudiana has poor aqueous solubility and dissolution qualities in beverage formulations.

Method used

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  • Compositions and methods for improving rebaudioside x solubility
  • Compositions and methods for improving rebaudioside x solubility
  • Compositions and methods for improving rebaudioside x solubility

Examples

Experimental program
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example 1

Purification of Reb X from Stevia rebaudiana Bertoni Plant Leaves

[0553]Two kg of Stevia rebaudiana Bertoni plant leaves were dried at 45° C. to an 8.0% moisture content and ground to 10-20 mm particles. The content of different glycosides in the leaves was as follows: Stevioside—2.55%, Reb A—7.78%, Reb B—0.01%, Reb C—1.04%, Reb D—0.21%, Reb F—0.14%, Reb X—0.10% Dulcoside A—0.05%, and Steviolbioside—0.05%. The dried material was loaded into a continuous extractor and the extraction was carried out with 40.0 L of water at a pH of 6.5 at 40° C. for 160 min. The filtrate was collected and subjected to chemical treatment. Calcium oxide in the amount of 400 g was added to the filtrate to adjust the pH within the range of 8.5-9.0, and the mixture was maintained for 15 min with slow agitation. Then, the pH was adjusted to around 3.0 by adding 600 g of FeCl3 and the mixture was maintained for 15 min with slow agitation. A small amount of calcium oxide was further added to adjust the pH to 8....

example 2

Structural Elucidation of Rebaudioside X

[0563]HRMS: HRMS (High Resolution Mass Spectrum) data was generated with a Waters Premier Quadrupole Time-of-Flight (Q-TOF) mass spectrometer equipped with an electrospray ionization source operated in the positive-ion mode. Samples were diluted and eluted with a gradient of 2:2:1 methanol:acetonitrile:water and introduced 50 μL via infusion using the onboard syringe pump

[0564]NMR: The sample was dissolved in deuterated pyridine (C5D5N) and NMR spectra were acquired on Varian Unity Plus 600 MHz instruments using standard pulse sequences. The chemical shifts are given in δ (ppm), and coupling constants are reported in Hz.

[0565]The complete 1H and 13C NMR spectral assignments for the diterpene glycoside rebaudioside X determined on the basis of 1D (1H and 13C) and 2D (COSY, HMQC and HMBC) NMR as well as high resolution mass spectroscopic data:

[0566]Discussion

[0567]The molecular formula was deduced as C56H90O33 on the basis of its positive high r...

example 3

Preparation and Characterization of Form A Rebaudioside X

[0573]X-ray amorphous Rebaudioside X was added to a 1:1 mixture of methanol and water to provide a slurry. The slurry was stirred at room temperature overnight. The X-ray diffraction pattern of the Rebaudioside X obtained is shown in FIG. 1. Form A was successfully indexed, indicating that the sample is composed primarily of a single crystalline phase. Prominent peaks are provided below:

TABLE 1Form A Rebaudioside X Prominent XPRD°2Θd space (Å)Intensity (%) 3.76 ± 0.2023.489 ± 1.319 67 6.50 ± 0.2013.594 ± 0.431 58 6.62 ± 0.2013.354 ± 0.416 89 6.79 ± 0.2013.025 ± 0.395 100 9.93 ± 0.208.909 ± 0.1833612.33 ± 0.207.176 ± 0.1184012.45 ± 0.207.109 ± 0.1164913.69 ± 0.206.469 ± 0.0954414.06 ± 0.206.301 ± 0.0905015.44 ± 0.205.738 ± 0.0753716.25 ± 0.205.456 ± 0.0684616.80 ± 0.205.278 ± 0.0636620.44 ± 0.204.345 ± 0.04248

[0574]Non-systematic peak shifts between the X-ray diffraction patterns of Form A are observed (FIG. 2) and are likely d...

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Abstract

Polymorphic and amorphous forms of Rebaudioside X and methods for preparing the same are provided herein. Also provided herein are Rebaudioside X complexes and methods for preparing the same. Sweetener compositions and sweetened compositions comprising Rebaudioside X forms and Rebaudioside X complexes are described, as well as and methods of their preparation. Methods of improving the flavor and / or temporal profile of sweetenable compositions, such as beverages, are also provided herein.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation of International Application No. PCT / US2012 / 070564, filed Dec. 19, 2012.FIELD OF THE INVENTION[0002]The present invention relates generally to crystalline forms and amorphous Rebaudioside X and methods of preparing the same. The present invention also relates to Rebaudioside X complexes and methods of preparing the same. Certain forms of Rebaudioside X and the Rebaudioside X complexes are advantageous compared to other forms of Rebaudioside X because of improved aqueous solubility. The present invention also encompasses sweetener compositions and sweetened compositions comprising amorphous Rebaudioside X and Rebaudioside X complexes in addition to methods for preparing the same.BACKGROUND OF THE INVENTION[0003]Stevia is the common name for Stevia rebaudiana (Bertoni), a perennial shrub of the Asteracae (Compositae) family native to Brazil and Paraguay. The plant's leaves, the aqueous extract of the leave...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07H15/24A61K47/36A23L1/236A23L27/30
CPCA23V2002/00A23L27/36C07H15/24C07H15/256A23V2250/262A23L27/33A61K8/602A61K47/26A61Q11/00C07C31/24C08B37/0009C08B37/0015
Inventor PRAKASH, INDRAMARKOSYAN, AVETIKCHATURVEDULA, VENKATA SAI PRAKASHMA, GIL
Owner THE COCA-COLA CO
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