5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 154731
• Molecular Formular: C27H30O15
• Molecular Mass: 594.5181
• Monoisotopic Mass: 594.15847026
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)O)O)O)O)O)O
• Canonical SMILES: Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
• InChIKey: RTATXGUCZHCSNG-QHWHWDPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one
• Synonyms: 3,4′,5,7-Tetrahydroxyflavone 3-rhamnoglucoside; Nicotiflorin; Kaempferol 3-O-β -rutinoside; Kaempferol 3-rutinoside; Nicotiflorin

Database IDs

• CAS Number: 17650-84-9
• MDL Number: MFCD03427292
• PubChem SID: 162248869
• PubChem CID: 5318767

CALCULATED PROPERTIES

• Acid pKa: 6.372348
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -0.619655
• LogD (pH = 7.4): -1.72132
• Log P: -0.5651957
• Molar Refractivity: 138.1642 cm^3
• Polarizability: 54.612293 Å^3
• Polar Surface Area: 245.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC); 98.0
• Empirical Formula (Hill Notation): C27H30O15

DETAILS

Sigma Aldrich - 90242

General description
Kaempferol 3-O-β -rutinoside is a bitter tasting flavonol glycoside that was isolated from flowers of a Clematis cultivar. 1