C7727

Curcumin

≥94% (curcuminoid content), ≥80% (Curcumin)

• Synonym(s): (E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Diferuloylmethane, Diferulylmethane, Natural Yellow 3
• Linear Formula: [HOC₆H₃(OCH₃)CH=CHCO]₂CH₂
• CAS Number: 458-37-7
• Molecular Weight: 368.38
• Colour Index Number: 75300
• Beilstein/REAXYS Number: 2306965
• EC Number: 207-280-5
• MDL number: MFCD00008365
• UNSPSC Code: 12352205
• PubChem Substance ID: 24892983
• NACRES: NA.47

Properties

• vapor density: 13 (vs air)
• assay: ≥80% (Curcumin); ≥94% (curcuminoid content)
• form: powder
• mp: 175 °C
• solubility: ethanol: 1 mg/mL; DMSO: >11 mg/mL; 0.5 M NaOH: soluble (then immediately diluted in PBS)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: −20°C
• SMILES string: COc1cc(\C=C\C(=O)CC(=O)\C=C\c2ccc(O)c(OC)c2)ccc1O
• 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/b7-3+,8-4+
• InChI key: VFLDPWHFBUODDF-FCXRPNKRSA-N
• Gene Information: human ... APP(351) , CYP1A2(1544)

Description

General description

Curcumin is a yellow colored polyphenol obtained from the rhizome of Curcuma longa L. It is also known as diferuloyl methane, a symmetric molecule with a seven carbon linker connecting two o-methoxy phenolic groups containing aromatic rings. Curcumin is synthesized by Pabon′s reaction using vanillin and acetyl acetone in the presence of boric oxide. It constitutes an important part of various diets and herbal medicines, especially in the Asian continent for its various salubrious effects on human health.

Application

Curcumin has been used:

• to study its in vitro effect on the inflammation and expression of tumour factor in patients with chronic kidney diseases
• to determine its influence when used in combination with high frequency ultrasound on human cervical carcinoma cells
• to study the possibility of using magnetic purification of curcumin from Curcuma longa by surface active maghemite nanoparticles (SAMNs)
• to examine its effect on the amyloid-β peptide levels along with the maturation of amyloid-β precursor proteins in various cell lines and primary cortical neurons in mouse
• as a supplement to evaluate its anti-carcinogenic and anti-apoptotic effect on cancer cells and cardiomyocytes
• to test its anti-inflammatory effect in human promyelocytic leukemia cell line, the HL-60

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. 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.

Curcumin is postulated to have anti-depressant, anti-stress and neuroprotective effects on humans and other animals. Additionally, it also shows anti-fungal, antiviral, anti-microbial, chemosensitizing, radiosensitizing, and wound healing activities.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable