Naringin dihydrochalcone

Naringin dihydrochalcone
Names
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
Systematic IUPAC name
3,5-Dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-L-glucopyranoside
Other names
Naringin DC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.127.977 Edit this at Wikidata
UNII
  • InChI=1S/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m0/s1 ☒N
    Key: CWBZAESOUBENAP-IKACCGSXSA-N ☒N
  • InChI=1/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m0/s1
    Key: CWBZAESOUBENAP-IKACCGSXBG
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2Oc3cc(c(c(c3)O)C(=O)CCc4ccc(cc4)O)O)CO)O)O)O)O)O
Properties
C27H34O14
Molar mass 582.555 g·mol−1
Appearance White powder
Melting point 169 to 170 °C (336 to 338 °F; 442 to 443 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

[edit]
  1. ^ Ikan, R. (1991). "1-Flavonoides. E. Synthesis of Naringin Dihydrochalcone — A Sweetening Agent". Natural Products: A Laboratory Guide (2nd ed.). Academic Press. pp. 17–18. ISBN 0-12-370551-7.
  2. ^ Tomasik, P., ed. (2003). Chemical and Functional Properties of Food Saccharides. Boca Raton: CRC Press. p. 389. ISBN 978-0-84-931486-5.
[edit]
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