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458-37-7 molecular structure
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1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

ChemBase ID: 81908
Molecular Formular: C21H20O6
Molecular Mass: 368.3799
Monoisotopic Mass: 368.12598836
SMILES and InChIs

SMILES:
O=C(/C=C/c1ccc(c(c1)OC)O)CC(=O)/C=C/c1cc(c(cc1)O)OC
Canonical SMILES:
COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O
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

Cite this record

CBID:81908 http://www.chembase.cn/molecule-81908.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
(1E,6E)-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
Curcumin
Natural Yellow3
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
(E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
Diferulylmethane
Curcumin
Diferuloylmethane
C.I. 75300
Natural Yellow 3
Curcumin
Curcuminoid
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
Curcuma yellow
(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
C Yellow 15
C.I. Natural Yellow 3
Curcuma
Curcumin I
Curcumine
Haidr
Halad
Haldar
Ukon
姜黄素
CAS Number
458-37-7
EC Number
207-280-5
MDL Number
MFCD00008365
Beilstein Number
2306965
Merck Index
142673
PubChem SID
24892983
162069027
24892408
PubChem CID
969516
CHEBI ID
3962
CHEMBL
116438
Chemspider ID
839564
Unique Ingredient Identifier
IT942ZTH98
Wikipedia Title
Curcumin
Curcuminoid
Color Index Number
75300
E Number
E100

CALCULATED PROPERTIES

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 cm3 Polarizability 38.873188 Å3
Polar Surface Area 93.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.5 M NaOH: soluble (then immediately dilute in PBS) expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
DMSO: >11 mg/mL expand Show data source
ethanol: soluble10 mg/mL expand Show data source
Apperance
Bright Orange Solid expand Show data source
Bright Yellow
to orange powder
expand Show data source
Bright yellow-orange powder expand Show data source
orange powder expand Show data source
Melting Point
162-163°C expand Show data source
170-175°C expand Show data source
175-180 °C expand Show data source
183°C expand Show data source
Vapor Density
13 (vs air) expand Show data source
Storage Condition
Refrigerator expand Show data source
Storage Warning
Irritant expand Show data source
RTECS
MI5230000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-36 expand Show data source
26-36/37 expand Show data source
26-36/37/39 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Gene Information
human ... APP(351), CYP1A2(1544) expand Show data source
Mechanism of Action
Acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage expand Show data source
Induce glutathione S-transferase and are potent inhibitors of cytochrome P450; expand Show data source
Inhibitor of eicosanoid biosynthesis expand Show data source
Purity
~70% (HPLC) expand Show data source
≥95.0% (TLC) expand Show data source
≥98.0% (HPLC) expand Show data source
95% (total curcuminoid content), from Turmeric rhizome expand Show data source
Grade
analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Description
Tautomers expand Show data source
Biological Source
from Curcuma longa (Turmeric) expand Show data source
Isol. from Curcuma zedoaria (turmeric), other Curcuma spp. and other spp. expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Application(s)
Antiamyloid expand Show data source
Antiarthritic expand Show data source
Antiinflammatory agent expand Show data source
Antitumor expand Show data source
Bile stimulant showing hepatoprotective props expand Show data source
Possesses bactericidal and fungicidal props. expand Show data source
Linear Formula
[HOC6H3(OCH3)CH=CHCO]2CH2 expand Show data source

DETAILS

DETAILS

InterBioScreen InterBioScreen Wikipedia Wikipedia TRC TRC Sigma Aldrich Sigma Aldrich
Toronto Research Chemicals - C838500 external link
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
Sigma Aldrich - C1386 external link
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.
Sigma Aldrich - 28260 external link
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.
Sigma Aldrich - 08511 external link
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.

REFERENCES

REFERENCES

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  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 800B, (nmr)
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  • • Srinivasan, K.R., J. Pharm. Pharmacol., 1953, 5, 448, (derivs)
  • • Spicer, G.S. et al., Anal. Chim. Acta, 1958, 18, 231, (detn, B)
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  • • Dyrssen, D.W. et al., Anal. Chim. Acta, 1972, 60, 139, (detn, B)
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PATENTS

PATENTS

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INTERNET

INTERNET

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