Neohesperidin Dihydrochalcone

Category

Sweetening agent

Molecular Formula

C28H36O15

Molecular Weight

612.58

Description

Neohesperidin dihydrochalcone occurs as a white or yellowish white powder with an intensely sweet taste.

UNII

NA

Chemical Name

1-[4-[[2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl] oxy]-2, 6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one

CAS Number

20702-77-6

Synonyms

Citrosa; 3, 5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)- phenyl-2-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside; 3, 5-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propionyl]phenyl- 2-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside; E959; neohesperidin DC; neohesperidin DHC; neohesperidin dihydrochalconum; neohesperidine dihydrochalcone; NHDC; 1- propanone; 1-[4-[[2-O-6-deoxy-a-L-mannopyranosyl)-b-D-glycopyranosyl] oxy]-2, 6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl); Sukor.

Stability and Storage Conditions

Neohesperidin dihydrochalcone is stable for over three years when stored at room temperature.Accelerated stability studies on aqueous solutions stored at 30-60℃ 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.

Source and Preparation

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.

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.

Incompatibilities

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