Naringin dihydrochalcone

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Naringin dihydrochalcone
250px
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
18916-17-1 YesY
ChemSpider 23089598 N
Jmol 3D model Interactive image
PubChem 25245680
  • 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 582.55 g·mol−1
Appearance White powder
Melting point 169 to 170 °C (336 to 338 °F; 442 to 443 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

  1. Lua error in package.lua at line 80: module 'strict' not found.
  2. Lua error in package.lua at line 80: module 'strict' not found.