2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-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 trihydrate

• ChemBase ID: 155100
• Molecular Formular: C27H36O19
• Molecular Mass: 664.56334
• Monoisotopic Mass: 664.18507893
• 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(c(c1)O)O)O)O)O)O)O)O)O)O.O.O.O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O[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)c1ccc(c(c1)O)O.O.O.O
• InChI: InChI=1S/C27H30O16.3H2O/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;3*1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;;;/m0.../s1
• InChIKey: NLLBWFFSGHKUSY-JPRRWYCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-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 trihydrate
• IUPAC Traditional name: troxerutin trihydrate
• Synonyms: Quercetin-3-rutinoside hydrate; Vitamin P hydrate; Rutin hydrate; Quercetin-3-rutinoside trihydrate; Vitamin P trihydrate; Rutin trihydrate; Quercetin-3-rutinoside 水合物; Vitamin P 水合物; 芦丁 水合物; 维生素 P 三水合物; 芸香甙 三水合物; 芦丁 三水合物

Database IDs

• CAS Number: 250249-75-3; 207671-50-9
• EC Number: 205-814-1
• MDL Number: MFCD00149490
• Beilstein Number: 75455
• PubChem SID: 24888176; 24887256; 162249238; 24899379
• PubChem CID: 16218542

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: aqueous base: soluble; DMSO: soluble; pyridine: soluble50 mg/mL
• Apperance: yellow to green powder
• Melting Point: 195 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +9±2°, c = 0.5% in absolute ethanol; [α]24/D +10.4°, c = 2 in ethanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥90% (HPLC); ≥94% (HPLC); ≥95.0% (HPLC); 95%
• Grade: analytical standard; primary reference standard
• Salt Data: 3 H2O
• Empirical Formula (Hill Notation): C27H30O16 · 3H2O; C27H30O16 · xH2O
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 84082

Other Notes
Review2
Biochem/physiol Actions
Rutin is the major mutagenic component of red wine; it is not itself mutagenic, but is activated to a mutagen by treatment both liver microsomal enzymes and fecal enzymes.1

Sigma Aldrich - R5143

Biochem/physiol Actions
A polyphenolic flavonoid that acts as an antioxidant and NO scavenger. It can attenuate peroxide production in glial cells by acting as a free radical scavenger and protect renal cells from oxidative injury. Inclusion of rutin in the diet of rats significantly reduced the appearance of single-strand breaks in nuclear DNA caused by hepatocarcinogens aflatoxin B1 and N-nitrosodimethylamine. This protection from DNA damage was found to be due to a reduction in the induction of repair enzymes polymerase, DNA polymerase β and DNA ligase. Since DNA damage and inefficient repair are thought to initiate the process of carcinogenesis, effects of rutin on these functions suggests a protective role of this flavonoid against carcinogenesis induced by chemical carcinogens.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 00300590

Application
Reference standard in the analysis of herbal medicinal products.
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate

Sigma Aldrich - R2303

Packaging
5, 500 g in glass bottle