Megastigmane derivative compositions and methods for taste modulation

Patent metadata

Field	Value
Publication number	US-2024000119-A1
Application number	US-202118253630-A
Country	US
Kind code	A1
Filing date	Dec 15, 2021
Priority date	Nov 25, 2020
Publication date	Jan 4, 2024
Grant date	—

Abstract

The use of a megastigmane derivative to enhance the sweetness of a sweetness modifier and to decrease the amount of a sweetness modifier used in a consumable is provided.

First claim

What is claimed is:

1 . A method of enhancing the sweetness of a sweetness modifier comprising the step of adding to the sweetness modifier an olfactory effective amount of a megastigmane derivative of Formula I:

wherein one of R 1 and R 2 represents hydrogen and the other one thereof represents a sugar moiety;
R 3 , R 4 , R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen, a methyl group and a hydroxy group, or R 4 and R together form a group —O—; and
wherein a dashed line represents an optional carbon-carbon double bond, with the proviso that the dashed line between carbon atom 2 and carbon atom 3 and the dashed line between carbon atom 3 and carbon atom 4 do not simultaneously represent a carbon-carbon double bond; and
with the further proviso that when the dashed line between carbon atom 1 and oxygen represents a carbon-carbon double bond, R 1 is absent, when the dashed line between carbon atom 2 and carbon atom 3 represents a carbon-carbon double bond, R 4 is absent, and when the dashed line between carbon atom 3 and carbon atom 4 represents a carbon-carbon double bond, R 4 and R 5 are absent.

2 . The method of claim 1 , wherein the megastigmane derivative having Formula II:

wherein R 1′ represents hydrogen and R 2′ represents a sugar moiety;
R 3′ , R 4′ , R 5′ , R 5′ and R 7′ are independently selected from the group consisting of hydrogen, a methyl group and a hydroxy group; and
wherein a dashed line represents an optional carbon-carbon double bond, with the proviso that the dashed line between carbon atom 2 and carbon atom 3 and the dashed line between carbon atom 3 and carbon atom 4 do not simultaneously represent a carbon-carbon double bond; and
with the further proviso that when the dashed line between carbon atom 1 and oxygen represents a carbon-carbon double bond, R 1 is absent, when the dashed line between carbon atom 2 and carbon atom 3 represents a carbon-carbon double bond, R 4 is absent, and when the dashed line between carbon atom 3 and carbon atom 4 represents a carbon-carbon double bond, R 4 and R 5 are absent.

3 . The method of claim 2 , wherein the megastigmane derivative is selected from the group consisting of lauroside A, ampelopsisionoside, bridelionoside F, phlomisionoside, actinidioionoside, (3S,5R,6R,7E,9S)-megastigm-7-ene-3,5,6,9-tetrol 3-(β-D-glucopyranoside), stratioside II, 3-hydroxy-5,6-epoxy-β-ionyl-β-D-glucopyranoside, staphylionoside E, plucheoside B, alangionoside D, roseoside and a mixture thereof.

4 . The method of claim 1 , wherein the sweetness modifier is a natural sweetener selected from the group consisting of sucrose, fructose, glucose, high fructose corn syrup, rebaudioside A, stevioside, rebaudioside D, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.

5 . The method of claim 1 , wherein the sweetness modifier is an artificial sweetener selected from the group consisting of aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.

6 . The method of claim 1 , wherein the olfactory effective amount is from about 0.1 ppb to about 500 ppm of the sweetness modifier.

7 . The method of claim 1 , wherein the olfactory effective amount is from about 1 ppb to about 100 ppm of the sweetness modifier.

8 . The method of claim 1 , wherein the olfactory effective amount is from about 10 ppb to about 10 ppm of the sweetness modifier.

9 . The method of claim 1 , wherein the megastigmane derivative is provided as a botanical extract of a plant selected from the group consisting of Eriobotrya japonica, Antidesma bunius, Diospyros maritima, Passiflora incarnata Linn., Opuntia humifusa, Persea americana, Laurus nobilis, Garcinia mangostana, Syzygium samarangense, Antidesma pentandrum var. barbatum, Cirsium setosum, Cinnamomum wilsonii, Antidesma ghaesembilla, Vitis quinguangularis Rehd, Annona muricate and Phoenix dactylifera.

10 . The method of claim 1 , wherein the method further comprising the step of adding an olfactory effective amount of a flavoring.

11 . The method of claim 10 , wherein the flavoring is stevia composition.

12 . The method of claim 11 , wherein the olfactory effective amount is from about 1 ppm to about 5000 ppm of the sweetness modifier.

13 . The method of claim 11 , wherein the megastigmane and the stevia composition have a weight ratio of about 1:50-5000.

14 . A composition comprising a sweetness modifier and a sweetness enhancer containing a megastigmane derivative.

15 . The composition of claim 14 , wherein the sweetness enhancer further comprising a stevia composition.

16 . The composition of claim 14 , wherein the sweetness modifier is a natural sweetener selected from the group consisting of sucrose, fructose, glucose, high fructose corn syrup, rebaudioside A, stevioside, rebaudioside D, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, inositol and a combination thereof.

17 . The composition of claim 14 , wherein the sweetness modifier is an artificial sweetener selected from the group consisting of aspartame, sucralose, neotame, acesulfame potassium, saccharin and a combination thereof.

18 . The composition of claim 14 , wherein the megastigmane derivative is selected from the group consisting of lauroside A, ampelopsisionoside, bridelionoside F, phlomisionoside, actinidioionoside, (3S,5R,6R,7E,9S)-megastigm-7-ene-3,5,6,9-tetrol 3-(β-D-glucopyranoside), stratioside II, 3-hydroxy-5,6-epoxy-β-ionyl-β-D-glucopyranoside, staphylionoside E, plucheoside B, alangionoside D, roseoside and a mixture thereof.

19 . The composition of claim 15 , wherein the megastigmane and the stevia composition have a weight ratio of about 1:50-5000.

20 . A consumable comprising a sweetness modifier and a sweetness enhancer containing a megastigmane derivative and a stevia composition, wherein the megastigmane and the stevia composition have a weight ratio of about 1:50-5000.

Assignees

• Int Flavors & Fragrances Inc

Inventors

• Wu Hou
• Cheng Diana Klaser
• John Thumpalasseril V
• Huber Michelle Eve
• Ubaideen Hassan Mustaq
• Li Jing
• Tang Xiao-Qing
• Hou Yanpeng
• Singh Ajay Pratap

Classifications

• A23L27/34 Primary

  Sugar alcohols · CPC title

• A23L27/10

  Natural spices, flavouring agents or condiments; Extracts thereof · CPC title

• A23L27/88

  Taste or flavour enhancing agents · CPC title

• A23L27/33 Primary

  containing sugars or derivatives · CPC title