Naringin dihydrochalcone

Naringin dihydrochalcone
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 Image 1
Properties
Molecular formula C27H34O14
Molar mass 582.55 g/mol
Exact mass 582.194856 u
Appearance White powder
Melting point

169-170°C
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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, a compound roughly 300-1800 times sweeter than sugar at threshold concentrations[2].

References

  1. ^ (English) Raphael Ikan. Natural products: a laboratory guide. Publié par Academic Press, 1991. 360 pages. ISBN 0123705517. Chapitre 1-Flavonoides, E. Synthesis of Naringin Dihydrochalcone— A Sweetening Agent. pages 17-18.
  2. ^ (English) P Tomasik, Chemical and Functional Properties of Food Saccharides, CRC Press, 2003, 440 p. (ISBN 9780849314865), p. 389
v · 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
Stub icon This article about a natural phenol is a stub. You can help Wikipedia by expanding it.