1-(4-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-(2H3)methoxyphenyl]propan-1-one

• ChemBase ID: 175071
• Molecular Formular: C28H36O15
• Molecular Mass: 612.57644
• Monoisotopic Mass: 612.20542045
• SMILES: c1(cc(c(c(c1)O)C(=O)CCc1cc(c(cc1)OC)O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)C)O)O)O)O)O)CO
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cc(O)c(c(c2)O)C(=O)CCc2ccc(c(c2)O)OC)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChIKey: ITVGXXMINPYUHD-CUVHLRMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-(^2H₃)methoxyphenyl]propan-1-one
• IUPAC Traditional name: 1-(4-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-(^2H₃)methoxyphenyl]propan-1-one
• Synonyms: 1-[4-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-(methoxy-d3)-phenyl)-1-propanone; NHDC-d3; Neohesperidin DC-d3; Neohesperidin DHC-d3; Neohesperidine Dihydrochalcone-d3; Neohesperidin Dihydrochalcone-d3

Database IDs

• PubChem SID: 164230981
• PubChem CID: 71750989

CALCULATED PROPERTIES

• Acid pKa: 9.56446
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): 0.74583834
• LogD (pH = 7.4): 0.74292827
• Log P: 0.7458755
• Molar Refractivity: 143.1845 cm^3
• Polarizability: 57.31882 Å^3
• Polar Surface Area: 245.29 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: >155°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N389952

Preparation from Naringen, a flavanone glycoside occurring naturally in grapefruit. It is used as sweetening agent, especially in chewing gum and dentifrices.

REFERENCES

• Fisher, J.F., J. Agric. Food Chem., 25, 682 (1969)
• Pratter, P.J., Perfum. Flavor., 5, 12 (1969)
• Lina, B.A.R., et al.: Food Chem. Toxicol., 28, 507 (1969)
• Inglett, et al.: J. Food Sci., 34, 101 (1969)