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

基本信息

化学结构

分子式

C₁₅H₁₀O₆

分子量

286.2363

精确质量

286.04773804

电荷

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

计算属性

JChem

Acid pKa

6.5745034

质子受体

质子供体

LogD (pH = 5.5)

2.3681753

LogD (pH = 7.4)

1.4610965

Log P

2.4031239

摩尔折射率

74.8948

极化性

27.752142

极化表面积

107.22

可自由旋转的化学键

里宾斯基五规则

true

数据来源

名称和标识

别名

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传统名

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

IUPAC标准名

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

名称和标识

数据登录号

EC号

Beilstein号

MDL号

CAS号

PubChem SID

2489652024882269162036326

默克索引号

145614

PubChem CID

5280445

数据登录号

化合物性质

药理学性质

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

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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).

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

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

IUPAC标准名

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

数据登录号

EC号

Beilstein号

MDL号

CAS号

PubChem SID

2489652024882269162036326

默克索引号

PubChem CID

描述信息

S2320

L9283

L475000

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

参考文献

PubChem文献

数据源提供

• 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).

生物活性

PubChem BioAssay

化合物性质

药理学性质

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

化合物信息

ID:70611