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...

General Information

Structure

Molecular Formula

C₂₁H₂₀O₆

Molecular Mass

368.3799

Exact Mass

368.12598836

Charge

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

Calculated Properties

JChem

Acid pKa

9.061334

H Acceptors

H Donor

LogD (pH = 5.5)

4.124406

LogD (pH = 7.4)

4.1151395

Log P

4.1245246

Molar Refractivity

103.8106

Polarizability

38.873188

Polar Surface Area

93.06

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

(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 Traditional name

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

Synonyms

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

Names and Identifiers

Registration numbers

CAS Number

458-37-7

Color Index Number

75300

E Number

E100

PubChem SID

2489240824892983162069027

MDL Number

EC Number

Beilstein Number

CHEMBL

Wikipedia Title

Unique Ingredient Identifier

Merck Index

PubChem CID

CHEBI ID

Chemspider ID

Registration numbers

Properties

Pharmacology Properties

Gene Information

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

Mechanism of Action

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;

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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

Molecule Details

References

PubChem Literature

From Data Sources

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

• Chem. and Eng. News 90(1953)

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

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

• 44 (2012)

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

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

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

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

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

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

References

Bioactivity

PubChem BioAssay

Bioactivity