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

[0010]Amorphous Rebaudioside X has improved solubility properties compared to other forms of Rebaudioside X, including Form A Rebaudioside X. In one embodiment, amorphous Rebaudioside X has an aqueous solubility greater than about 0.3%.

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
Comparison scheme
Effect test

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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