00280590

Curcumin

primary reference standard

• 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
• EC Number: 207-280-5
• UNSPSC Code: 85151701
• NACRES: NA.24
• PubChem Substance ID: 329747028
• MDL number: MFCD00008365
• Colour Index Number: 75300
• Beilstein/REAXYS Number: 2306965

Properties

• InChI key: VFLDPWHFBUODDF-FCXRPNKRSA-N
• 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+
• SMILES string: COc1cc(\C=C\C(=O)CC(=O)\C=C\c2ccc(O)c(OC)c2)ccc1O
• grade: primary reference standard
• vapor density: 13 (vs air)
• form: powder or crystals
• shelf life: limited shelf life, expiry date on the label
• manufacturer/tradename: HWI
• technique(s): HPLC: suitable, gas chromatography (GC): suitable

Description

General description

Curcumin is a bioactive component of turmeric, Curcuma longa. It has a broad spectrum of activities including antioxidant, anti-inflammatory and being anti-cancerous in nature. It has been shown to be a very powerful antioxidant, and has been found to enhance the effects of common anti-cancer drugs. It can also modulate several molecular targets such as cytokines and chemokines, a multitude of enzymes, receptors, transcription factors, cell cycle proteins and cell surface adhesion molecules.[1]

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Application

It has been used as reference standard in 1H NMR and LC–MS/MS analysis for the quantification of curcumin in turmeric.[2]

Reference Standard in the analysis of herbal medicinal products

Biochem/physiol Actions

A natural phenolic compound responsible for the yellow color of turmeric. Potent anti-tumor agent that acts against highly diverse tumor-specific pathways. Anti-inflammatory and anti-oxidant. 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), cyclooxygenase (COX-2) and 5-lipoxygenase (5-LOX).

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.

Other Notes

This compound is commonly found in plants of the genus: curcuma

Safety Information

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