1-(4-{[(2R,3S,4R,6S)-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-(4-hydroxyphenyl)propan-1-one

• ChemBase ID: 120138
• Molecular Formular: C27H34O14
• Molecular Mass: 582.55046
• Monoisotopic Mass: 582.19485577
• SMILES: [C@H]1([C@H](O[C@H](C([C@H]1O)O)CO)Oc1cc(c(c(c1)O)C(=O)CCc1ccc(cc1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2cc(O)c(c(c2)O)C(=O)CCc2ccc(cc2)O)[C@H]([C@@H](C1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: 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
• InChIKey: CWBZAESOUBENAP-UECFNAJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-{[(2R,3S,4R,6S)-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-(4-hydroxyphenyl)propan-1-one
• IUPAC Traditional name: 1-(4-{[(2R,3S,4R,6S)-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-(4-hydroxyphenyl)propan-1-one
• Synonyms: Naringin DC; Naringin dihydrochalcone; 1-(4-(((2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl )propan-1-one

Database IDs

• CAS Number: 18916-17-1
• PubChem SID: 162214491
• PubChem CID: 66523441

CALCULATED PROPERTIES

• Acid pKa: 9.337157
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): 0.903484
• LogD (pH = 7.4): 0.89857626
• Log P: 0.90354675
• Molar Refractivity: 136.7213 cm^3
• Polarizability: 54.758804 Å^3
• Polar Surface Area: 236.06 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Product Information

• Application(s): Artificial sweetener

REFERENCES

• 1. Raphael Ikan. Natural products: a laboratory guide. Publie' par Academic Press, 1991. 360 pages. ISBN 0123705517. Chapitre 1-Flavonoides, E. Synthesis of Naringin Dihydrochalcone?A Sweetening Agen
• t. pages 17-18.
• 2. P Tomasik, Chemical and Functional Properties of Food Saccharides, CRC Press, 2003, 440 p. (ISBN 9780849314865), p. 389