Mogroside Compound Structures for Sweetness Without Bitter Aftertaste
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Solution Overview
Problem
Existing natural sweeteners like mogrosides from Siraitia grosvenori (luo han guo) often impart a bitter aftertaste, limiting their broader adoption as sugar substitutes, despite being significantly sweeter than sucrose.
Innovation Solution
Development of mogroside compounds with specific sugar moieties and stereoisomers, such as 22-hydroxy-mogroside IVa, 22-hydroxy-mogroside III, and 22-hydroxy-isomogroside IVa, which enhance sweetness without the bitter aftertaste.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If natural sweeteners like mogrosides are used to replace sugar, then sweetness intensity is improved (100 times sweeter than sucrose), but bitter aftertaste is generated which limits broader adoption
Solution Approach 1:
The patent modifies the chemical structure of mogrosides by changing parameters such as the type of sugar moieties (glucose, galactose, mannose, etc.), their linkage positions, and stereochemical configurations (e.g., 22-hydroxy-mogroside IVa, 22-hydroxy-mogroside III). These structural parameter changes result in compounds that maintain high sweetness intensity while eliminating or reducing the bitter aftertaste associated with conventional mogrosides.
Solution Approach 2:
The invention creates composite sweetening compounds by combining mogrol/oxo-mogrol core structures with various sugar moiety units (monosaccharides and oligosaccharides). This composite approach allows the integration of different functional groups to achieve both high sweetness and reduced bitter aftertaste, as seen in compounds like 1-[(6-O-hexopyranosylhexopyranosyl)oxy]-11,22,25-trihydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholest-5-en-24-yl 6-O-hexopyranosylhexopyranoside.
2Loss of energy
If conventional mogrosides are used as sugar substitutes, then caloric content is reduced (close to zero calories), but taste quality deteriorates due to bitter aftertaste
Solution Approach 1:
The patent systematically varies chemical parameters of mogroside compounds, including the types of sugar moieties attached to the core structure, the position of hydroxyl groups, and stereochemical configurations. These parameter changes enable the creation of low-calorie sweeteners that avoid the bitter aftertaste problem while maintaining the zero-calorie benefit.
3Quantity of substance
If existing sweeteners like sucralose, aspartame, and acesulfame potassium are used, then sweetness intensity is achieved at very low doses, but natural preference is lost due to artificial taste profile
Solution Approach 1:
The patent creates natural sweetening compounds that copy the molecular structure and taste profile of natural sugars and fruits. By using naturally occurring sugar moieties (glucose, galactose, mannose, fructose, etc.) attached to the mogrol core, the compounds replicate the taste characteristics of natural sweeteners while achieving high intensity sweetness, thereby eliminating the artificial taste profile of conventional sweeteners like sucralose and aspartame.
Data Source
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AI summary
The various aspects presented herein relate to processes for preparing food ingredients, flavors and sweeteners from extracts of plants that contain mogrosides such as Siraitia grosvenorii. Further provided herein are formulations and uses of compositions made from the processes.