CAS 491-70-3|Luteolol|3'|5|luteolin|4'|Luteoline|Luteolin|2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one|7-Tetrahydroxyflavone|2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one|3′,4′,...

General Information

Structure

Molecular Formula

C₁₅H₁₀O₆

Molecular Mass

286.2363

Exact Mass

286.04773804

Charge

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

Canonic Smiles

Oc1cc(O)c2c(c1)oc(cc2=O)c1ccc(c(c1)O)O

Isomeric Smiles

c1(cc(=O)c2c(cc(cc2o1)O)O)c1cc(c(cc1)O)O

Calculated Properties

JChem

Acid pKa

6.5745034

H Acceptors

H Donor

LogD (pH = 5.5)

2.3681753

LogD (pH = 7.4)

1.4610965

Log P

2.4031239

Molar Refractivity

74.8948

Polarizability

27.752142

Polar Surface Area

107.22

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

53'LuteololLuteolineLuteolin7-Tetrahydroxyflavone4'2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one3′,4′,5,7-TetrahydroxyflavoneLuteolinDaphneflavonolLuteolin3',4',5,7-四羟基黄酮3',4',5,7-TetrahydroxyflavoneFlavopurpolDigitoflavone3',4',5,7-TetrahydroxyflavoneCyanidenon 1470Weld lakeCyanidenonSalifazide2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-oneYama Kariyasu2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneFlacitran

IUPAC Traditional name

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

IUPAC name

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

Names and Identifiers

Registration numbers

EC Number

Beilstein Number

MDL Number

CAS Number

PubChem SID

2489652024882269162036326

Merck Index

145614

PubChem CID

5280445

Registration numbers

Properties

Pharmacology Properties

human ... CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), GSK3A(2931)mouse ... Hexa(15211)rat ... Il4(287287), Tnf(24835)

Lipid peroxidation inhibitor in rat liver microsomes

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

TRC

L475000

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Nagarathnam, D. et al., J.O.C., 1991, 56, 4884, (synth)

• Chari, V.M. et al., Phytochemistry, 1977, 16, 1273, (nmr)

• Youssef, D. et al., Planta Med., 1995, 61, 570, (pmr, cmr)

• Voirin, B., Phytochemistry, 1983, 22, 2107, (uv)

• Nevskaya, E.M., Zh. Anal. Khim., 1972, 27, 1699, (use)

• Plant Flavonoids in Biology and Medicine, (eds. Cody, V. et al), A. R. Liss, N. Y., 1986, (biol, prop)

• Inouye, H. et al., Chem. Ber., 1969, 102, 3009, (synth)

• 1994, 87, 107, (Luteolin, pharmacol)

• Mansour, R.M.A. et al., Phytochemistry, 1983, 22, 2630, (derivs)

• Kingston, D.G.I., Tetrahedron, 1971, 27, 2691, (ms)

• Markham, K.R. et al., J. Nat. Prod., 1987, 50, 660, (derivs)

• Diller, E., Ber., 1901, 34, 1452, (isol)

• Ono, K., Eur. J. Biochem., 1990, 190, 469, (anti-HIV activity)

• Dhar, K.L. et al., Planta Med., 1970, 18, 337, (isol, deriv)

• Wagner, H. et al., Tet. Lett., 1976, 1799, (nmr)

• Thieme, H., Tet. Lett., 1968, 2781, (derivs)

• Bandyukova, V.A., Khim. Prir. Soedin., 1969, 5, 595

• El-Ansari, M.A. et al., Phytochemistry, 1991, 30, 1169, (derivs)

• Perkin, A.G., J.C.S., 1900, 77, 1315, (isol)

• Litkei, G. et al., Annalen, 1995, 1711, (synth)

• Tomas, F. et al., Z. Naturforsch., C, 1985, 40, 583

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1470; 1473, (occur)

• Cody, V. et al., Plant Flavonoids in Biology and Medicine II, (eds., Cody, V. et al), A.R. Liss, N.Y., 1988, (biol, prop)

• Anti-oxidant and radical scavenger in biological systems: Methods Enzymol., 234, 420 (1994).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

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

IUPAC name

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

Registration numbers

EC Number

Beilstein Number

MDL Number

CAS Number

PubChem SID

2489652024882269162036326

Merck Index

PubChem CID

Molecule Details

S2320

L9283

L475000

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

References

PubChem Literature

From Data Sources

• 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

• Nagarathnam, D. et al., J.O.C., 1991, 56, 4884, (synth)

• Chari, V.M. et al., Phytochemistry, 1977, 16, 1273, (nmr)

• Youssef, D. et al., Planta Med., 1995, 61, 570, (pmr, cmr)

• Voirin, B., Phytochemistry, 1983, 22, 2107, (uv)

• Nevskaya, E.M., Zh. Anal. Khim., 1972, 27, 1699, (use)

• Plant Flavonoids in Biology and Medicine, (eds. Cody, V. et al), A. R. Liss, N. Y., 1986, (biol, prop)

• Inouye, H. et al., Chem. Ber., 1969, 102, 3009, (synth)

• 1994, 87, 107, (Luteolin, pharmacol)

• Mansour, R.M.A. et al., Phytochemistry, 1983, 22, 2630, (derivs)

• Kingston, D.G.I., Tetrahedron, 1971, 27, 2691, (ms)

• Markham, K.R. et al., J. Nat. Prod., 1987, 50, 660, (derivs)

• Diller, E., Ber., 1901, 34, 1452, (isol)

• Ono, K., Eur. J. Biochem., 1990, 190, 469, (anti-HIV activity)

• Dhar, K.L. et al., Planta Med., 1970, 18, 337, (isol, deriv)

• Wagner, H. et al., Tet. Lett., 1976, 1799, (nmr)

• Thieme, H., Tet. Lett., 1968, 2781, (derivs)

• Bandyukova, V.A., Khim. Prir. Soedin., 1969, 5, 595

• El-Ansari, M.A. et al., Phytochemistry, 1991, 30, 1169, (derivs)

• Perkin, A.G., J.C.S., 1900, 77, 1315, (isol)

• Litkei, G. et al., Annalen, 1995, 1711, (synth)

• Tomas, F. et al., Z. Naturforsch., C, 1985, 40, 583

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1470; 1473, (occur)

• Cody, V. et al., Plant Flavonoids in Biology and Medicine II, (eds., Cody, V. et al), A.R. Liss, N.Y., 1988, (biol, prop)

• Anti-oxidant and radical scavenger in biological systems: Methods Enzymol., 234, 420 (1994).

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

human ... CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), GSK3A(2931)mouse ... Hexa(15211)rat ... Il4(287287), Tnf(24835)

Lipid peroxidation inhibitor in rat liver microsomes

Molecule

ID:70611