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Merck

00280590

Curcumin

primary reference standard

Synonym(e):

(E,E)-1,7-Bis-(4-Hydroxy-3-methoxyphenyl)-1,6-heptadien-3,5-dion, Diferuloylmethan, Natural Yellow 3

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About This Item

Lineare Formel:
[HOC6H3(OCH3)CH=CHCO]2CH2
CAS-Nummer:
Molekulargewicht:
368.38
Farbindexnummer:
75300
Beilstein:
2306965
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
85151701
PubChem Substanz-ID:
NACRES:
NA.24

Qualität

primary reference standard

Dampfdichte

13 (vs air)

Form

powder or crystals

Haltbarkeit

limited shelf life, expiry date on the label

Hersteller/Markenname

HWI

Methode(n)

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+

InChIKey

VFLDPWHFBUODDF-FCXRPNKRSA-N

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

Eine natürliche Phenolverbindung. Wirksames Antitumor-Mittel mit entzündungshemmenden und antioxidativen Eigenschaften. Curcumin wurde, zusätzlich zu seiner chemotherapeutischen Wirkung, als potenzielles chemopräventives Mittel beschrieben. Leitet die Apoptose in Krebszellen ein und hemmt die Phorbolester-induzierte Proteinkinase C (PKC)-Aktivität. Hemmt Berichten zufolge die Produktion von inflammatorischen Zytokinen durch Monozyten des peripheren Blutes und alveoläre Makrophagen. Wirksamer Inhibitor der EGFR-Tyrosinkinase und IκB-Kinase. Hemmt die induzierbare Stickoxidsynthase (iNOS), Cycloxygenase und Lipoxygenase. Dringt leicht in das Zytoplasma von Zellen ein, sammelt sich in membranösen Strukturen wie Plasmamembran, endoplasmatisches Retikulum und Kernhülle an.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Demethoxycurcumin ≥98% (HPLC)

Sigma-Aldrich

D7696

Demethoxycurcumin

Demethoxycurcumin analytical standard

Supelco

90593

Demethoxycurcumin

≥98% (HPLC), solid

Sigma-Aldrich

B6938

Bisdemethoxycurcumin

Bisdemethoxycurcumin analytical standard

Supelco

90594

Bisdemethoxycurcumin

Bisdemethoxycurcumin phyproof® Reference Substance

PHL89582

Bisdemethoxycurcumin

Demethoxycurcumin phyproof® Reference Substance

PHL89628

Demethoxycurcumin

USP

USP

1075305

Bisdesmethoxycurcumin

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
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)
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
Marie-Hélène Teiten et al.
Molecular nutrition & food research, 57(9), 1619-1629 (2013-06-12)
Epigenetic alterations correspond to changes in DNA methylation, covalent modifications of histones, or altered miRNA expression patterns. These three mechanisms are interconnected and appear to be key players in tumor progression and failure of conventional chemotherapy. Dietary components emerged as
Wing-Hin Lee et al.
Expert opinion on drug delivery, 11(8), 1183-1201 (2014-05-27)
Natural compounds are emerging as effective agents for the treatment of malignant diseases. Curcumin (diferuloylmethane), the active constituent of turmeric extract, has gained significant interest as a plant-based compound with anti-cancer properties. Curcumin is physiologically very well tolerated, with negligible

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