CAS 458-37-7|(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione|1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione|turmeric|Curcumin|Natural Yellow3|curcumin|(1E,6E)-1,7-Bi...

基本信息

化学结构

分子式

C₂₁H₂₀O₆

分子量

368.3799

精确质量

368.12598836

电荷

InChI

InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3

InChIKey

VFLDPWHFBUODDF-UHFFFAOYSA-N

Canonic Smiles

COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O

Isomeric Smiles

O=C(/C=C/c1ccc(c(c1)OC)O)CC(=O)/C=C/c1cc(c(cc1)O)OC

计算属性

JChem

Acid pKa

9.061334

质子受体

质子供体

LogD (pH = 5.5)

4.124406

LogD (pH = 7.4)

4.1151395

Log P

4.1245246

摩尔折射率

103.8106

极化性

38.873188

极化表面积

93.06

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

IUPAC标准名

(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione 1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

IUPAC传统名

turmeric curcumin (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

别名

CurcuminNatural Yellow3(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dioneDiferuloylmethane(E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dioneCurcuminDiferulylmethaneNatural Yellow 3(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dioneHaidrCurcumaC.I. 75300Curcumin IHaldarC Yellow 15CurcumineHaladC.I. Natural Yellow 3UkonCurcuminCurcuminoidCurcuma yellow1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione姜黄素

名称和标识

数据登录号

CAS号

458-37-7

Color Index Number

75300

E编码

E100

PubChem SID

2489240824892983162069027

MDL号

MFCD00008365

EC号

数据登录号

化合物性质

产品相关信息

~70% (HPLC)

≥95.0% (TLC)

≥98.0% (HPLC)

95% (total curcuminoid content), from Turmeric rhizome

from Curcuma longa (Turmeric)

Isol. from Curcuma zedoaria (turmeric), other Curcuma spp. and other spp.

药理学性质

human ... APP(351), CYP1A2(1544)

Inhibitor of eicosanoid biosynthesis

Acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage

Induce glutathione S-transferase and are potent inhibitors of cytochrome P450;

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

Tautomers

C1386

Biochem/physiol Actions
A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Curcumin has been cited as a potential chemopreventive agent, in addition to its chemotherapeutic activity.1 Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.

28260

08511

TRC

C838500

A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and antioxidant properties. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory

描述信息

参考文献

PubChem文献

数据源提供

• Tu, B., et al.: J .Cell Biol., 164, 341 (1953)

• Xu, G., et al.: Biochemistry, 44, 9817 (1953)

• Srinivasan, et al.: J. Pharm. Pharmacol., 5, 448 (1953)

• Johnson, J., et al.: Cancer Lett., 255, 170 (1953)

• Chem. and Eng. News 90(1953)

• 44 (2012)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 52C, (ir)

• Spicer, G.S. et al., Anal. Chim. Acta, 1958, 18, 231, (detn, B)

• Umland, F. et al., Fresenius' Z. Anal. Chem., 1963, 197, 151, (detn, Ni)

• Sastry, B.S., Res. Ind., 1970, 15, 258; CA, 75, 75063e, (isol)

• Quint, P. et al., Fresenius' Z. Anal. Chem., 1977, 285, 356; 1979, 295, 269, (detn, B)

• Roughley, P.J. et al., J.C.S. Perkin 1, 1973, 2379-2388, (biosynth)

• Kashina, C. et al., Heterocycles, 1977, 7, 241, (synth)

• Karig, F., Dtsch. Apoth. -Ztg., 1975, 115, 325; CA, 83, 65372f, (derivs)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 800B, (nmr)

• Kuroyagi, M. et al., Yakugaku Zasshi, 1970, 90, 1467; CA, 74, 61612a, (isol)

• Dyrssen, D.W. et al., Anal. Chim. Acta, 1972, 60, 139, (detn, B)

• Lampe, V., Ber., 1918, 51, 1347, (synth)

• Cheng, K.L. et al., Handbook of Organic Analytical Reagents, CRC Press, Boca Raton, 1982, 511, (use)

• Jentzsch, K. et al., Sci. Pharm., 1968, 36, 251; CA, 70, 90793h, (isol)

• Holder, G.M. et al., Xenobiotica, 1978, 8, 761, (metab)

• Ammon, H.P.T. et al., Planta Med., 1991, 57, 1-7, (rev, pharmacol)

• Jitoe, A. et al., J. Agric. Food Chem., 1992, 40, 1337-1340, (occur)

• Wahlstrom, B. et al., Acta Pharmacol. Toxicol., 1978, 43, 86, (metab)

• Srinivasan, K.R., J. Pharm. Pharmacol., 1953, 5, 448, (derivs)

• Tonnesen, H.H. et al., Acta Chem. Scand., Ser. B, 1982, 36, 475, (cryst struct, bibl)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione 1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

IUPAC传统名

turmeric curcumin (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

别名

描述信息

Tautomers

C1386

28260

08511

TRC

C838500

参考文献

PubChem文献

数据源提供

• Tu, B., et al.: J .Cell Biol., 164, 341 (1953)

• Xu, G., et al.: Biochemistry, 44, 9817 (1953)

• Srinivasan, et al.: J. Pharm. Pharmacol., 5, 448 (1953)

• Johnson, J., et al.: Cancer Lett., 255, 170 (1953)

• Chem. and Eng. News 90(1953)

• 44 (2012)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 52C, (ir)

• Spicer, G.S. et al., Anal. Chim. Acta, 1958, 18, 231, (detn, B)

• Umland, F. et al., Fresenius' Z. Anal. Chem., 1963, 197, 151, (detn, Ni)

• Sastry, B.S., Res. Ind., 1970, 15, 258; CA, 75, 75063e, (isol)

• Quint, P. et al., Fresenius' Z. Anal. Chem., 1977, 285, 356; 1979, 295, 269, (detn, B)

• Roughley, P.J. et al., J.C.S. Perkin 1, 1973, 2379-2388, (biosynth)

• Kashina, C. et al., Heterocycles, 1977, 7, 241, (synth)

• Karig, F., Dtsch. Apoth. -Ztg., 1975, 115, 325; CA, 83, 65372f, (derivs)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 800B, (nmr)

• Kuroyagi, M. et al., Yakugaku Zasshi, 1970, 90, 1467; CA, 74, 61612a, (isol)

• Dyrssen, D.W. et al., Anal. Chim. Acta, 1972, 60, 139, (detn, B)

• Lampe, V., Ber., 1918, 51, 1347, (synth)

• Cheng, K.L. et al., Handbook of Organic Analytical Reagents, CRC Press, Boca Raton, 1982, 511, (use)

• Jentzsch, K. et al., Sci. Pharm., 1968, 36, 251; CA, 70, 90793h, (isol)

• Holder, G.M. et al., Xenobiotica, 1978, 8, 761, (metab)

• Ammon, H.P.T. et al., Planta Med., 1991, 57, 1-7, (rev, pharmacol)

• Jitoe, A. et al., J. Agric. Food Chem., 1992, 40, 1337-1340, (occur)

• Wahlstrom, B. et al., Acta Pharmacol. Toxicol., 1978, 43, 86, (metab)

• Srinivasan, K.R., J. Pharm. Pharmacol., 1953, 5, 448, (derivs)

• Tonnesen, H.H. et al., Acta Chem. Scand., Ser. B, 1982, 36, 475, (cryst struct, bibl)

生物活性

PubChem BioAssay

数据登录号

CAS号

458-37-7

Color Index Number

75300

E编码

E100

PubChem SID

2489240824892983162069027

MDL号

MFCD00008365

EC号

化合物性质

产品相关信息

~70% (HPLC)

≥95.0% (TLC)

≥98.0% (HPLC)

95% (total curcuminoid content), from Turmeric rhizome

from Curcuma longa (Turmeric)

Isol. from Curcuma zedoaria (turmeric), other Curcuma spp. and other spp.

药理学性质

human ... APP(351), CYP1A2(1544)

Inhibitor of eicosanoid biosynthesis

Acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage

Induce glutathione S-transferase and are potent inhibitors of cytochrome P450;

分子相关蛋白质

化合物信息

ID:81908