2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

• ChemBase ID: 70611
• Molecular Formular: C15H10O6
• Molecular Mass: 286.2363
• Monoisotopic Mass: 286.04773804
• SMILES: c1(cc(=O)c2c(cc(cc2o1)O)O)c1cc(c(cc1)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
• InChIKey: IQPNAANSBPBGFQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
• IUPAC Traditional name: luteolin; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
• Synonyms: 3′,4′,5,7-Tetrahydroxyflavone; Luteolin; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one; 3'; 4'; 5; 7-Tetrahydroxyflavone; Luteoline; Luteolol; Luteolin; 3',4',5,7-Tetrahydroxyflavone; Digitoflavone; Flacitran; Salifazide; Weld lake; Yama Kariyasu; Cyanidenon; Cyanidenon 1470; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one; Luteolin; 3',4',5,7-Tetrahydroxyflavone; Daphneflavonol; Flavopurpol; 3',4',5,7-四羟基黄酮

Database IDs

• CAS Number: 491-70-3
• EC Number: 207-741-0
• MDL Number: MFCD00017309
• Beilstein Number: 292084
• Merck Index: 145614
• PubChem SID: 162036326; 24896520; 24882269
• PubChem CID: 5280445

CALCULATED PROPERTIES

• Acid pKa: 6.5745034
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.3681753
• LogD (pH = 7.4): 1.4610965
• Log P: 2.4031239
• Molar Refractivity: 74.8948 cm^3
• Polarizability: 27.752142 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Ethanol
• Apperance: Yellow Needles; yellow powder; Yellow powder
• Melting Point: ~330 °C(lit.); >220°C (dec.); >300°C

Safety Information

• Storage Condition: -20°C; Amber Vial, Refrigerator, Under Inert Atmosphere
• Storage Warning: IRRITANT
• RTECS: LK9275210
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), GSK3A(2931)mouse ... Hexa(15211)rat ... Il4(287287), Tnf(24835)
• Mechanism of Action: Lipid peroxidation inhibitor in rat liver microsomes

Product Information

• Purity: ≥97.0% (HPLC); ≥98% (TLC); ≥99.0% (TLC); 95+%; 97%; 98%; 98.5
• Grade: analytical standard
• Salt Data: Free Base
• Biological Source: Occurs in many plants in Leguminosae, Resedaceae, Euphorbiaceae, Umbelliferae, Scrophulariaceae, Fabaceae, Asteraceae, Cistaceae, Passifloraceae, Yerbenaceae and Hepaticae. First isol. in 1832 from Reseda luteola
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antiinflammatory; Antispasmodic; Antitumourigenic activity in mice reported; Antitussive agent; Shows anti-HIV activity
• Empirical Formula (Hill Notation): C15H10O6

DETAILS

Selleck Chemicals - S2320

Research Area: Inflammation
Biological Activity:
Luteolin is a PDE4 inhibitor and a general phosphodiesterase inhibitor, and an Interleukin 6 inhibitor. It significantly reversed the xylazine/ketamine-induced anesthesia in mice. Luteolin is a flavonoid; more specifically, it is one of the more common flavones. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an agent in the prevention of inflammation, a promoter of carbohydrate metabolism, and an immune system modulator. These characteristics of luteolin are also believed to play an important part in the prevention of cancer. [1]References on Luteolin[1] http://en.wikipedia.org/wiki/Luteolin , ,

Sigma Aldrich - L9283

Biochem/physiol Actions
Hydroxylated flavone derivative, a strong antioxidant and radical scavenger. Suggested to play a role in prevention of cancer, possibly via the inhibition of fatty acid synthase activity.

Toronto Research Chemicals - L475000

Hydroxylated flavone derivative with strong anti-oxidant and radical scavenging properties. Suggested to play a role in cancer prevention.

REFERENCES

• http://en.wikipedia.org/wiki/Luteolin
• Shimoi, L., et al.: Carcinogenesis, 15, 2669 (1994)
• Bors, W., et al.: Meth. Enzymol., 234, 420 (1994)Merck Index 12th ed. 5641
• Perkin, A.G., J.C.S., 1900, 77, 1315, (isol)
• Diller, E., Ber., 1901, 34, 1452, (isol)
• Thieme, H., Tet. Lett., 1968, 2781, (derivs)
• Inouye, H. et al., Chem. Ber., 1969, 102, 3009, (synth)
• Bandyukova, V.A., Khim. Prir. Soedin., 1969, 5, 595
• 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)
• Markham, K.R. et al., J. Nat. Prod., 1987, 50, 660, (derivs)
• Cody, V. et al., Plant Flavonoids in Biology and Medicine II, (eds., Cody, V. et al), A.R. Liss, N.Y., 1988, (biol, prop)
• Ono, K., Eur. J. Biochem., 1990, 190, 469, (anti-HIV activity)
• Nagarathnam, D. et al., J.O.C., 1991, 56, 4884, (synth)
• El-Ansari, M.A. et al., Phytochemistry, 1991, 30, 1169, (derivs)
• 1994, 87, 107, (Luteolin, pharmacol)
• Litkei, G. et al., Annalen, 1995, 1711, (synth)
• Youssef, D. et al., Planta Med., 1995, 61, 570, (pmr, cmr)
• Anti-oxidant and radical scavenger in biological systems: Methods Enzymol., 234, 420 (1994).