2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 154727
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: c1cc(c(cc1c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
• InChIKey: PEFNSGRTCBGNAN-QNDFHXLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: luteolin 7-O-glucoside; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• Synonyms: Luteolin 7-O-β-D-glucoside; Luteolin 7-O-β-D-glucoside; Luteolin 7-glucoside; Luteolin 7-O-glucoside; Luteolin 7-glucoside; Glucoluteolin; Cinaroside; Cynaroside; Daphneflavonoloside; Flavopurposide; Luteoloside; Cynaroside

Database IDs

• CAS Number: 5373-11-5
• EC Number: 226-365-8
• MDL Number: MFCD06799436
• PubChem SID: 162248865
• PubChem CID: 5280637

CALCULATED PROPERTIES

• Acid pKa: 7.2968016
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 0.12822835
• LogD (pH = 7.4): -0.22765297
• Log P: 0.13505572
• Molar Refractivity: 107.0392 cm^3
• Polarizability: 41.507587 Å^3
• Polar Surface Area: 186.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

Safety Information

• RTECS: DJ3009400
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: eNOS mRNA expression inducer; eNOS promoter

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC); 98.0
• Grade: analytical standard
• Biological Source: Widespread in plants. The commonest of all flavone glycosides
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antiischaemic agent
• Empirical Formula (Hill Notation): C21H20O11

DETAILS

Sigma Aldrich - 74284

Biochem/physiol Actions
Luteolin 7-O-β-D-glucoside is a plant flavonoid which possesses antioxidant, antiviral, and antibacterial properties.
General description
Luteolin 7-O-β-D-glucoside is a flavonoid recently isolated from the Bidens parviflora Wild plant. 1

REFERENCES

• Perkin, A.G., J.C.S., 1900, 77, 1315, (isol)
• Diller, E., Ber., 1901, 34, 1452, (isol)
• Lovecy, A. et al., J.C.S., 1930, 817
• Hattori, S. et al., J.A.C.S., 1954, 76, 5792, (Glucoluteolin)
• Thieme, H., Tet. Lett., 1968, 2781, (derivs)
• Inouye, H. et al., Chem. Ber., 1969, 102, 3009, (synth)
• Dhar, K.L. et al., Planta Med., 1970, 18, 337, (isol, deriv)
• Kingston, D.G.I., Tetrahedron, 1971, 27, 2691, (ms)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1470; 1473, (occur)
• Nevskaya, E.M., Zh. Anal. Khim., 1972, 27, 1699, (use)
• Wagner, H. et al., Tet. Lett., 1976, 1799, (nmr)
• Chari, V.M. et al., Phytochemistry, 1977, 16, 1273, (nmr)
• Voirin, B., Phytochemistry, 1983, 22, 2107, (uv)
• Mansour, R.M.A. et al., Phytochemistry, 1983, 22, 2630, (derivs)
• Tomas, F. et al., Z. Naturforsch., C, 1985, 40, 583
• Plant Flavonoids in Biology and Medicine, (eds. Cody, V. et al), A. R. Liss, N. Y., 1986, (biol, prop)
• Medicine II, (eds., Cody, V. et al), A.R. Liss, N.Y., 1988, (biol, prop)