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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

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About This Item

Linear Formula:
[HOC6H3(OCH3)CH=CHCO]2CH2
CAS Number:
Molecular Weight:
368.38
Colour Index Number:
75300
Beilstein:
2306965
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

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

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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.
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.
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.

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Rapid quantitation of curcumin in turmeric via NMR and LC?tandem mass spectrometry.
Goren, Ahmet C., et al.
Food Chemistry, 113.4, 1239-1242 (2009)
B Antony et al.
Indian journal of pharmaceutical sciences, 70(4), 445-449 (2008-07-01)
Curcumin, the bioactive component of turmeric, Curcuma longa has an exceptionally wide spectrum of activities including antioxidant, anti-inflammatory and anti-cancer properties, and is currently under different phases of clinical trials for various types of soft tissue cancers. However, although in
Jingjing Zhu et al.
Biochimica et biophysica acta, 1833(8), 1924-1935 (2013-04-16)
Proprotein convertases (PCs) form a group of serine endoproteases that are essential for the activation of proproteins into their active form. Some PCs have been proposed to be potential therapeutic targets for cancer intervention because elevated PC activity has been
Bharat B Aggarwal et al.
Molecular nutrition & food research, 57(9), 1529-1542 (2013-07-13)
Turmeric, a dried powder derived from the rhizome of Curcuma longa, has been used for centuries in certain parts of the world and has been linked to numerous biological activities including antioxidant, anti-inflammatory, anticancer, antigrowth, anti-arthritic, anti-atherosclerotic, antidepressant, anti-aging, antidiabetic
Yoshikane Yamauchi et al.
Phytotherapy research : PTR, 28(5), 728-735 (2013-08-15)
Resistance to erlotinib in lung cancer cases includes T790M mutant epidermal growth factor receptor and c-Met gene amplification, but other unknown mechanisms account for about 30% of the resistance. Activation of the nuclear factor kappa B (NFkappaB)-related pathways in association

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