2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-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: 72993
• Molecular Formular: C33H42O19
• Molecular Mass: 742.67518
• Monoisotopic Mass: 742.23202912
• SMILES: c1c(cc2c(c1O)c(=O)c(c(o2)c1cc(c(cc1)OCCO)OCCO)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)OCCO
• Canonical SMILES: OCCOc1cc(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)OCCO)OCCO
• InChI: InChI=1S/C33H42O19/c1-14-23(38)26(41)28(43)32(49-14)48-13-21-24(39)27(42)29(44)33(51-21)52-31-25(40)22-17(37)11-16(45-7-4-34)12-20(22)50-30(31)15-2-3-18(46-8-5-35)19(10-15)47-9-6-36/h2-3,10-12,14,21,23-24,26-29,32-39,41-44H,4-9,13H2,1H3/t14-,21+,23-,24+,26+,27-,28+,29+,32+,33-/m0/s1
• InChIKey: IYVFNTXFRYQLRP-VVSTWUKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-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: THR; ruven
• Synonyms: Trihydroxyethylrutin; Troxerutin (INN); Troxerutin; 3′,4′,7-Tris[O-(2-hydroxyethyl)]rutin; Troxerutin; Trihydroxyethylrutin

Database IDs

• CAS Number: 7085-55-4
• EC Number: 230-389-4
• MDL Number: MFCD00893813
• Beilstein Number: 4778232
• PubChem SID: 24889589; 162037913
• PubChem CID: 5486699

CALCULATED PROPERTIES

• Acid pKa: 8.342624
• H Acceptors: 19
• H Donor: 10
• LogD (pH = 5.5): -2.5020032
• LogD (pH = 7.4): -2.5479064
• Log P: -2.5013847
• Molar Refractivity: 172.4689 cm^3
• Polarizability: 68.46069 Å^3
• Polar Surface Area: 293.21 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -48±1°, c = 1% in pyridine

Safety Information

• Storage Condition: -20°C
• RTECS: LK8331500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥80% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C33H42O19

DETAILS

Selleck Chemicals - S2369

Research Area: Cardiovascular Disease
Biological Activity:
Troxerutin(Trihydroxyethylrutin) is a flavonol, a type of flavonoid. It is more accurately a hydroxyethylrutoside. It can be isolated from Sophora japonica, the japanese pagoda tree.It is used as a vasoprotective. [1]

Sigma Aldrich - 91950

Biochem/physiol Actions
Shows widespread protective effects against oxidative DNA damage induced by D-galactose1,2 as well as other types of oxidative stress.3

REFERENCES

• http://en.wikipedia.org/wiki/Troxerutin