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EP-4159050-B1 - STEVIOL GLYCOSIDE COMPOSITIONS FOR ORAL INGESTION OR USE

EP4159050B1EP 4159050 B1EP4159050 B1EP 4159050B1EP-4159050-B1

Inventors

  • CARLSON, TING LIU
  • GASPARD, Dan S.
  • GUTHRIE, BRIAN D.
  • MORTENSON, MICHAEL ALAN

Dates

Publication Date
20260513
Application Date
20161130

Claims (9)

  1. A method of making a sweetener composition suitable for oral ingestion or oral use, comprising: adding a sensory modifying amount of one or more of compounds SG201, SG203, or SG204 according to the following structures: and an amount of one or more of Reb M, Reb D, Reb B or Reb A, wherein a sensory modifying amount of one or more of compounds SG201, SG203, or SG204 is in the range of 0.05 % to 10 % (wt) of a total amount of steviol glycosides in the composition.
  2. The method of claim 1, comprising adding a sensory modifying amount of two or more of compounds SG201, SG203, or SG204.
  3. The method of any one of claims 1-2, comprising adding an amount of two or more of Reb M, Reb D, Reb B or Reb A.
  4. The method of any one of claims 1-3, wherein the composition has Reb M, Reb D or a combination of Reb M and Reb D.
  5. The method of any one of claims 1-4, wherein the composition has Reb A.
  6. The method of any one of claims 1-5, wherein the sensory modifying amount of one or more of SG201, SG203, or SG204 enhances at least one of roundedness, temporal onset, tailing, sweetness, stringency, or a flavor note.
  7. The method of any one of claims 1-6, wherein at least one of compounds SG201, SG203, or SG204 is in an amount that has a sucrose equivalent value of less than about 1.5.
  8. The method of any one of claims 1-7, wherein Reb M or Reb D, or a combination thereof, is present in an amount greater than any one of compounds SG201, SG203, or SG204.
  9. The method of any one of claims 1-8, wherein the composition is a sweetener composition, a beverage, or a throw syrup.

Description

FIELD The present disclosure relates to compositions including a plurality of steviol glycosides. The present disclosure also relates to sweetener compositions and sweetened compositions including a combination of distinct steviol glycosides, and a method of making a sweetener composition suitable for oral ingestion or oral use, and uses of such sweetener compositions to prepare sweetened compositions including food, beverages, dental products, pharmaceuticals, nutraceuticals, and the like. The invention is restricted to the subject-matter of the claims. BACKGROUND Sugars, such as sucrose, fructose and glucose, are utilized to provide a pleasant taste to beverages, foods, pharmaceuticals, and oral hygienic/cosmetic products. Sucrose, in particular, imparts a taste preferred by consumers. Although sucrose provides superior sweetness characteristics, it is caloric. Non-caloric or lower caloric sweeteners have been introduced to satisfy consumer demand, and there is desire for these types of sweeteners that have favorable taste characteristics. Stevia is a genus of about 240 species of herbs and shrubs in the sunflower family (Asteraceae), native to subtropical and tropical regions from western North America to South America. The species Stevia rebaudiana, commonly known as sweetleaf, sweet leaf, sugarleaf, or simply stevia, is widely grown for its sweet leaves. Stevia-based sweeteners may be obtained by extracting one or more sweet compounds from the leaves. Many of these compounds are steviol glycosides, which are glycosides of steviol, a diterpene compound. These diterpene glycosides are about 150 to 450 times sweeter than sugar. Examples of steviol glycosides are described in published International application WO 2013/096420 (see, e.g., the listing in Fig. 1); and in Ohta et al., "Characterization of Novel Steviol Glycosides from Leaves of Stevia rebaudiana Morita," J. Appl. Glycosi., 57, 199-209 (2010) (See, e.g., Table 4 at p. 204). Structurally, the diterpene glycosides are characterized by a single base structure, steviol, and differ by the presence of carbohydrate residues at positions C13 and C19. See also PCT Patent Publication WO 2013/096420. Typically, on a dry weight basis, the four major steviol glycosides found in the leaves of Stevia are dulcoside A (0.3%), Reb C (0.6-1.0%), Reb A (3.8%) and stevioside (9.1%). Other glycosides identified in Stevia extract include one or more of Reb B, D, E, F, G, H, I, J, K, L, M, N, O, steviolbioside and rubusoside. While the major steviol glycoside Reb A is commonly used as sweetener in beverage applications it has off-taste issues. More recently, there has been focus on certain minor steviol glycosides which have better taste properties. For example, Reb M has higher sweetness intensity and is more potent than other steviol glycosides (e.g., see Prakash, I., et al. (2013) Nat. Prod. Commun., 8: 1523-1526, and WO 2013/096420). Reb D tastes about 200-220 times sweeter than sucrose and in a sensory evaluation it had a slow onset of sweetness and was very clean (e.g., see Prakash, I., et al. (2012) Int. J. Mol. Sci., 13:15126-15136). Some minor rebaudiosides can be challenging to use because they have less than desirable water solubility properties. For example, it has been reported that Reb D is difficult to use in food products because of its low solubility in water at room temperature. For instance, Reb D needs to be heated to near boiling water temperature for 2 hours in order to achieve complete dissolution at 0.8% concentration. At most only 300 to 450 ppm can be solubilized in water at 23° C (e.g., see US 2013/0251881). As another example, Reb M obtained from Stevia rebaudiana has poor aqueous solubility and dissolution qualities in beverage formulations (e.g., see US 2014/0171519). Certain methods to improve rebaudioside solubility are less than desirable because they are labor intensive, requiring high processing temperatures and the use of excipient compounds. For example, see WO 2013/148177. WO 2016/120486 A1 relates to recombinant microorganisms and methods for producing steviol glycosides, glycosylated ent-kaurenol, and glycosylated ent-kaurenoic acid. US 2014/342043 A1 discloses sweetener compositions suitable for use in beverage products and other food products. US 2013/309389 A1 discloses sweetener compositions comprising particular glycoside blends. WO 2014/086890 A1 discloses materials and methods for producing particular steviol glycosides, and high-purity compositions of particular steviol glycosides with improved sensory profiles. SUMMARY The present invention is defined in the appended claims. In particular, the invention provides a method of making a sweetener composition suitable for oral ingestion or oral use, comprising: adding a sensory modifying amount of one or more of compounds SG201, SG203, or SG204 according to the following structures: and an amount of one or more of Reb M, Reb D, Reb B or Reb A, wherein a sensory modifying