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Curcumin

Name: Curcumin
Brand: SIAL

matrix substance for MALDI-MS, ≥99.5% (HPLC)

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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:

2306965

EC Number:

207-280-5

MDL number:

MFCD00008365

PubChem Substance ID:

329768129

NACRES:

NA.21

grade

matrix substance for MALDI-MS

Quality Level

100

vapor density

13 (vs air)

Assay

≥99.5% (HPLC)

form

powder

technique(s)

MALDI-MS: suitable

mp

183-188 °C

cation traces

Na: ≤50 mg/kg

storage temp.

2-8°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

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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.

related product

Product No.

Description

Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Recent advances in curcumin nanoformulation for cancer therapy.

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

SAR studies on curcumin's pro-inflammatory targets: discovery of prenylated pyrazolocurcuminoids as potent and selective novel inhibitors of 5-lipoxygenase.

Andreas Koeberle et al.

Journal of medicinal chemistry, 57(13), 5638-5648 (2014-06-13)

The anticarcinogenic and anti-inflammatory properties of curcumin have been extensively investigated, identifying prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), key enzymes linking inflammation with cancer, as high affinity targets. A comparative structure-activity study revealed three modifications dissecting mPGES-1/5-LO inhibition, namely

Curcumin-free turmeric exhibits anti-inflammatory and anticancer activities: Identification of novel components of turmeric.

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

Coadministration of erlotinib and curcumin augmentatively reduces cell viability in lung cancer cells.

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

Molecular understanding of curcumin in diabetic nephropathy.

Vivian Soetikno et al.

Drug discovery today, 18(15-16), 756-763 (2013-05-09)

Diabetic nephropathy is characterized by a plethora of signaling abnormalities. Recent trials have suggested that intensive glucose-lowering treatment leads to hypoglycemic events, which can be dangerous. Curcumin is the active ingredient of turmeric, which has been widely used in many

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