Dihydrochalcones from Balanophora harlandii

Patent metadata

Field	Value
Publication number	US-12495818-B2
Application number	US-201917287345-A
Country	US
Kind code	B2
Filing date	Oct 22, 2019
Priority date	Oct 24, 2018
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

Methods of isolating dihydrochalcone compounds of Formula (I) from Balanophora harlandii are provided herein. Compositions and consumables comprising at least one sweetener and at least one dihydrochalcone compound described herein are also provided. Methods of enhancing the sweetness of a consumable, methods of making a consumable taste more like a sucrose-sweetened consumable and methods of preparing consumables are also detailed herein.

First claim

The invention claimed is:

1 . A beverage comprising rebaudioside M and at least one dihydrochalcone compound of Formula I:

wherein R 1 is OR 6 ;
R 6 is a saccharide substituted by one or more oxygens in the hydroxyl positions by galloyl, vanillyl, feruloyl, a monohydroxybenzoyl, dihydroxybenzoyl, trihydroxybenzoyl, or methoxybenzoyl;
R 2 is independently selected from OH and is OR 6 ;
R 3 is selected from hydrogen and CH 2 COOH; R 4 is selected from hydrogen and CH 3 ; and
wherein the rebaudioside M is present in a sweetening amount.

2 . The beverage of claim 1 , wherein the at least one dihydrochalcone compound of Formula I is selected from the group consisting of compounds of Formula Ia:

and combinations thereof.

3 . The beverage of claim 1 , wherein the beverage has up to about 40 calories per 8 ounce serving.

4 . The beverage of claim 1 , wherein the beverage is selected from the group consisting of a frozen carbonated beverage, enhanced sparkling beverage, cola, fruit-flavored sparkling beverage, ginger-ale, soft drink, root beer, fruit juice, fruit-flavored juice, juice drink, nectar, vegetable juice, vegetable-flavored juice, sports drink, energy drink, enhanced water drink, enhanced water with vitamins, near water drink, coconut water, black tea, green tea, red tea, oolong tea, coffee, cocoa drink, beverage containing milk components, beverage containing cereal extracts and a smoothie.

5 . The beverage of claim 3 , wherein the beverage is a fruit-flavored sparkling beverage.

6 . The beverage of claim 4 , wherein the beverage is an enhanced water drink.

7 . The beverage of claim 1 , wherein the beverage further comprises natural cola flavor, a colorant comprising caramel, an acidulant and caffeine.

8 . The beverage of claim 1 , wherein the at least one dihydrochalcone compound of Formula I is selected from the group consisting of compounds of Formula Ib:

and combinations thereof; wherein R 4′ is galloyl and R 5 is H.

9 . The beverage of claim 1 , the at least one dihydrochalcone compound of Formula I is 3-hydroxyphloretin-4′-O-[6″-O-galloyl]-β-D-glucoside.

10 . The beverage of claim 1 , the at least one dihydrochalcone compound of Formula I is 3-hydroxyphloretin-4′-O-[4″-O-galloyl]-β-D-glucoside.

11 . The beverage of claim 1 , wherein the at least one dihydrochalcone compound of Formula I is present in the beverage in a concentration from about 1 ppm to about 50 ppm.

12 . The beverage of claim 1 , wherein the rebaudioside M is present in the beverage in a concentration from about 50 ppm to about 600 ppm.

13 . The beverage of claim 1 , wherein the beverage has less than about 5 calories per 8 ounce serving.

14 . The beverage of claim 13 , wherein the beverage is a fruit-flavored sparkling beverage.

15 . The beverage of claim 1 , wherein the at least one dihydrochalcone compound of Formula I is selected from the group consisting of compounds of Formula Ib:

and combinations thereof, wherein R 4′ is H and R 5 is galloyl.

Assignees

• Coca Cola Co

Inventors

• Wang Bin
• Ma Gil
• Prakash Indra

Classifications

• A23L27/33

  containing sugars or derivatives · CPC title

• A23L27/36

  Terpene glycosides · CPC title

• C07H15/207

  Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins · CPC title

• C07H1/08

  from natural products · CPC title

• B01D15/426

  Specific type of solvent · CPC title