Neosperidin dihydrochalcone

Chemical Properties

Neohesperidin dihydrochalcone occurs as a white or yellowish white powder with an intensely sweet taste. The sweetness is about 1500-1800 times that of sucrose, and its sweetness time is slightly later than saccharin sodium and much faster than glycyrrhizin (5:7:23s). The sweetness retention time of the three is 42:57:133s, which is also between Between the two, it is closer to sodium saccharin. It is soluble in water, slightly soluble in ethanol, but insoluble in ether and benzene.

Uses

Neohesperidin dihydrochalcone hydrate, is a flavonoid sweetening agent with potent antioxidant activity. It is antioxidant agent. artificial sweetener, especially in chewing gum and dentifrices.

Uses

Preparation from Naringen, a flavanone glycoside occurring naturally in grapefruit. It is used as sweetening agent, especially in chewing gum and dentifrices.

Production Methods

Neohesperidin dihydrochalcone is synthesized commercially from either of the bitter-flavanones neohesperidin or naringin by catalytic hydrogenation under alkaline conditions in a process first described in the 1960s, in which neohesperidin is purified by recrystallization from water solutions.Neohesperidin dihydrochalcone is obtained by the alkaline hydrogenation of neohesperidin.

Definition

ChEBI: Neohesperidin dihydrochalcone is a member of the dihydrochalcones that is 3,2',4',6'-tetrahydroxy-4-methoxydihydrochalcone attached to a neohesperidosyl residue at position 4' via glycosidic linkage. It is found in sweet orange. It has a role as an environmental contaminant, a xenobiotic, a plant metabolite and a sweetening agent. It is a neohesperidoside, a disaccharide derivative and a member of dihydrochalcones.

Preparation

Neosperidin dihydrochalcone is produced from Neohespendin (an isomer of Hesperidin), derived from the peel of the Seville Orange.

General Description

Off-white crystals or powder. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Neosperidin dihydrochalcone is a ether-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Fire Hazard

The flash point of Neosperidin dihydrochalcone has not been determined, but Neosperidin dihydrochalcone is probably combustible.

Flammability and Explosibility

Not classified

Pharmaceutical Applications

Neohesperidin dihydrochalcone is a synthetic intense sweetening agent approximately 1500–1800 times sweeter than sucrose and 20 times sweeter than saccharin. Structurally it is an analogue of neohesperidin, a flavanone that occurs naturally in Seville oranges (Citrus aurantium). Neohesperidin dihydrochalcone is used in pharmaceutical and food applications as a sweetening agent and flavor enhancer. The sweetness profile is characterized by a lingering sweet/menthol-like aftertaste.The typical level used in foods is 1–5 ppm although much higher levels may be used in certain applications such as chewing gum. Synergistic effects occur with other intense and bulk sweeteners such as acesulfame K, aspartame, polyols, and saccharin.
In pharmaceutical applications, neohesperidin dihydrochalcone is useful in masking the unpleasant bitter taste of a number of drugs such as antacids, antibiotics, and vitamins. In antacid preparations, levels of 10–30 ppm result in improved palatability.

Safety

Neohesperidin dihydrochalcone is accepted for use in food products either as a sweetener or flavor modifier in a number of areas including Europe, USA, Australia, New Zealand, and several countries in Africa and Asia. It is also used in a number of oral pharmaceutical formulations.
Animal toxicity studies suggest that neohesperidin dihydrochalcone is a nontoxic, nonteratogenic, and noncarcinogenic material at the levels used in foods and pharmaceuticals.In Europe, an acceptable daily intake of 0–5 mg/kg body-weight has been established.

storage

Neohesperidin dihydrochalcone is stable for over three years when stored at room temperature.
Accelerated stability studies on aqueous solutions stored at 30–60°C and pH 1–7 for 140 days indicate that neohesperidin dihydrochalcone solutions are likely to be stable for 12 months at room temperature and pH 2–6.Solutions formulated with some or all of the water replaced by solvents with a lower dielectric constant are reported to have longer shelf-lives.
The bulk material should be stored in a cool, dry, place protected from light.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe.