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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

• Acid pKa: 9.061334
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 4.124406
• LogD (pH = 7.4): 4.1151395
• Log P: 4.1245246
• Molar Refractivity: 103.8106 cm^3
• Polarizability: 38.873188 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.5 M NaOH: soluble (then immediately dilute in PBS); Chloroform; DMSO; DMSO: >11 mg/mL; ethanol: soluble10 mg/mL
• Apperance: Bright Orange Solid; Bright Yellow; to orange powder; Bright yellow-orange powder; orange powder
• Melting Point: 162-163°C; 170-175°C; 175-180 °C; 183°C
• Vapor Density: 13 (vs air)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Irritant
• RTECS: MI5230000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36; 26-36/37; 26-36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... APP(351), CYP1A2(1544)
• Mechanism of Action: 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;; Inhibitor of eicosanoid biosynthesis

Product Information

• Purity: ~70% (HPLC); ≥95.0% (TLC); ≥98.0% (HPLC); 95% (total curcuminoid content), from Turmeric rhizome
• Grade: analytical standard
• Description: Tautomers
• Biological Source: from Curcuma longa (Turmeric); Isol. from Curcuma zedoaria (turmeric), other Curcuma spp. and other spp.
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antiamyloid; Antiarthritic; Antiinflammatory agent; Antitumor; Bile stimulant showing hepatoprotective props; Possesses bactericidal and fungicidal props.
• Linear Formula: [HOC6H3(OCH3)CH=CHCO]2CH2

DETAILS

InterBioScreen - BB_NC-1422

Tautomers

Toronto Research Chemicals - 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

Sigma Aldrich - 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.

Sigma Aldrich - 28260

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

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.

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