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

• ChemBase ID: 129338
• Molecular Formular: C27H30O16
• Molecular Mass: 610.5175
• Monoisotopic Mass: 610.15338488
• SMILES: CC1C(C(C(C(O1)OCC1C(C(C(C(O1)Oc1c(oc2cc(cc(c2c1=O)O)O)c1cc(c(cc1)O)O)O)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)OC1OC(COC2OC(C)C(C(C2O)O)O)C(C(C1O)O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3
• InChIKey: IKGXIBQEEMLURG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one
• IUPAC Traditional name: rutin
• Synonyms: Rutoside; Phytomelin; Sophorin; Birutan; Eldrin; Birutan Forte; Rutin trihydrate; Globularicitrin; Violaquercitrin; Rutin; 3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; Ilixathin; Melin; Rutabion; Rutinic Acid; Rutosid; Vitamin P; NSC 9220

Database IDs

• CAS Number: 153-18-4
• PubChem SID: 162223632
• PubChem CID: 5293655; 5280805
• ATC CODE: C05CA01
• Chemspider ID: 4444362
• DrugBank ID: DB01698
• KEGG ID: C05625
• Unique Ingredient Identifier: 5G06TVY3R7
• Wikipedia Title: Rutin

CALCULATED PROPERTIES

• Acid pKa: 6.4339614
• H Acceptors: 16
• H Donor: 10
• LogD (pH = 5.5): -0.91626626
• LogD (pH = 7.4): -1.8846226
• Log P: -0.868761
• Molar Refractivity: 140.1451 cm^3
• Polarizability: 55.293434 Å^3
• Polar Surface Area: 265.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 12.5 g/100 mL in water; DMSO; Ethanol; Methanol; Water
• Apperance: Pale-Yellow Solid; Solid
• Melting Point: 184-187°C (dec.); 242°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: VM2975000
• NFPA704:
  

  0

  2

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DETAILS

Toronto Research Chemicals - R701800

Found in many plants, especially the buckwheat plant. Identity with Ilixanthin. Capillary protectant. Rutin is colored brown by tobacco enzyme under experimental conditions.

REFERENCES

• Harrison, et al.: J. Am. Pharm. Assoc., 39, 557 (1950)
• Humphreys, et al.: Econ. Bot., 18, 195 (1950)
• Khalifa, T.I., et al.: Anal. Profiles Drug Subs., 12, 623 (1983).