Naringin dihydrochalcone

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Naringin dihydrochalcone

IUPAC name 1-[4-[(3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2, 6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Other names Naringin DC
Identifiers
CAS number	18916-17-1
PubChem	25245680
	Jmol-3D images	{{#if:C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H]([C@@H](OC2OC3=CC (=C(C(=C3)O)C(=O)CCC4=CC=C(C=C4)O)O)CO)O)O)O)O)O\|Image 1
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H]([C@@H](OC2OC3=CC (=C(C(=C3)O)C(=O)CCC4=CC=C(C=C4)O)O)CO)O)O)O)O)O
Properties
Molecular formula	C₂₇H₃₄O₁₄
Molar mass	582.55 g mol⁻¹
Appearance	White powder
Melting point	169-170 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Naringin dihydrochalcone, sometimes abbreviated to naringin DC, is an artificial sweetener derived from naringin, a bitter compound found in citrus.^[1]

Naringin dihydrochalcone is a phloretin glycoside discovered at the same time as neohesperidin dihydrochalcone during the 1960s as part of a United States Department of Agriculture research program to find methods for minimizing the taste of bitter flavorants in citrus juices.

When naringin is treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes a dihydrochalcone that is roughly 300-1800 times sweeter than sugar at threshold concentrations.^[2]

References

↑ Raphael Ikan (1991). "1-Flavonoides, E. Synthesis of Naringin Dihydrochalcone— A Sweetening Agent". Natural products: a laboratory guide. Academic Press. pp. 17–18. ISBN 0-12-370551-7.
↑ P Tomasik (2003). Chemical and Functional Properties of Food Saccharides. CRC Press. p. 389. ISBN 9780849314865.

v t e Dihydrochalcones and their glycosides

Dihydrochalcones:	3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol) 2′-hydroxy-3′,4′,5′,6′-tetramethoxychalcone (kanakugiol) 5-hydroxy-6,7,8-trimethoxyflavone (alnetin) methyl linderone 2′,3′,4′,5′,6′-pentamethoxychalcone (pedicellin) Phloretin Pinocembrin chalcone

Dihydrochalcone glycosides:	Aspalathin Naringin dihydrochalcone Neohesperidin dihydrochalcone Nothofagin Phlorizin

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