(2R)-7-{[(2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 302180
• Molecular Formular: C27H32O14
• Molecular Mass: 580.53458
• Monoisotopic Mass: 580.1792057
• SMILES: CC1[C@@H](C(C([C@@H](O1)OC1[C@@H]([C@@H](C(O[C@H]1Oc1cc(c2c(c1)O[C@H](CC2=O)c1ccc(cc1)O)O)CO)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2cc(O)c3c(c2)O[C@H](CC3=O)c2ccc(cc2)O)C([C@@H]([C@@H]1O)O)O[C@@H]1OC(C)[C@@H](C(C1O)O)O
• InChI: InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10?,16-,18?,20+,21-,22?,23-,24?,25?,26+,27-/m1/s1
• InChIKey: DFPMSGMNTNDNHN-KYYWYGCGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-7-{[(2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2R)-7-{[(2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one
• Synonyms: Naringin hydrate; 柚皮苷水合物

Database IDs

• CAS Number: 10236-47-2
• EC Number: 233-566-4
• MDL Number: MFCD00149445
• Beilstein Number: 102012
• Merck Index: 146424

CALCULATED PROPERTIES

• Acid pKa: 8.579344
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -0.15724456
• LogD (pH = 7.4): -0.18468763
• Log P: -0.15688573
• Molar Refractivity: 134.3038 cm^3
• Polarizability: 54.11746 Å^3
• Polar Surface Area: 225.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: ca 166°C dec.
• Optical Rotation: -90 (c=1 in ethanol)

Safety Information

• RTECS: QN6340000
• TSCA Listed: 是

Product Information

• Purity: 98%

REFERENCES

• Bitter principle of grapefruit.