The following is an introduction to Neohesperidin dihydrochalcone in terms of its chemical structure, physicochemical properties, synthetic pathway, and functional applications:
Chemical Structure and Physicochemical Properties
Chemical structure: new hesperidin dihydrochalcone (NHDC) belongs to flavonoid derivatives, generated by new hesperidin hydrogenation reaction, containing dihydrochalcone skeleton and glycosidic groups, molecular formula C₂₈H₃₆O₁₅, molecular weight of 612.58. CAS number 20702 – 77 – 6.
Physical Properties: Appearance is white or slightly yellow crystalline powder, melting point 152 – 158°C. For solubility, the solubility is 0.2 g/L at 20°C and 653 g/L at 80°C.
Synthesis path
Raw material source: New Hesperidin can be extracted from natural citrus plants, also can be generated by naringin chemical conversion.
Hydrogenation reaction: New hesperidin is ring-opened under alkaline conditions to form chalcone, and then catalyzed hydrogenation by palladium carbon. The key to this reaction is to choose a suitable catalyst for the hydrogenation and reduction reaction, generally choose nickel and palladium catalyst.
Purification: High purity products are obtained through crystallization, washing and drying.
Functions and Applications
Sweetness characteristics: NHDC is a natural sweetener and flavor enhancer, both sweetness and special aroma, sweetness up to 1500 – 2000 times that of sucrose, fresh taste, long-lasting aftertaste, and no off-flavors after sugar alcohols, the sweetness of the time needed to produce than saccharin sodium longer, but can last longer. It can also shield the bitter taste, and saccharin sodium synergy can make the sweet effect than the theoretical maximum value of nearly 40%, compared with a single sweetener can greatly reduce production costs.
Food industry: It can be directly used in food industry to improve the taste of food and beverage, for the improvement, enhancement and overall improvement of the flavor of food and beverage.
Feed industry: It is widely used in feed production. The compounding of neohesperidin dihydrochalcone and sodium saccharin is a high-intensity sweetener product, whose carriers are vanilla and dextrose with flavoring effect, which can enhance the appetite of piglets, promote growth and reduce feed consumption.
Pharmaceutical field: It has various pharmacological effects, such as inhibiting the proliferation of gastric cancer cells (Caco-2 cell IC₅₀ 0.17mM), regulating blood glucose (activating PPAR – γ receptor to improve insulin sensitivity), anti-CCL₄ caused by hepatic fibrosis in mice, lowering the cholesterol and neutral lipid content, preventing arteriosclerosis and vascular circulatory system, and preventing atherosclerosis. It can prevent cardiovascular complications such as atherosclerosis and vascular circulatory diseases, lower blood sugar (it can inhibit mammalian α-amylase to varying degrees, reducing the body’s absorption of sugar), and so on.
Cosmetic field: It has the function of removing free radicals in the skin, promoting skin metabolism, reducing pigmentation, moisturizing the skin, etc. The in vitro experiment found that its IC₅₀ of tyrosinase is 82.02µm/L, which is about 2 times and 60 times of whitening agent VC and β-arbutin, respectively, and the human body patch experiment found that it is non-irritating to the human body. The human spot patch experiment found no irritation to human body, and the total effective rate of 2% NHDC gel on melasma treatment was 89.6%, which can be expected to be used as a new type of whitening agent cosmetics.