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