78246
Curcumin
suitable for matrix substance for MALDI-MS, ≥99.5% (HPLC)
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
EC Number:
207-280-5
UNSPSC Code:
41115710
NACRES:
NA.21
PubChem Substance ID:
MDL number:
Colour Index Number:
75300
Beilstein/REAXYS Number:
2306965
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
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
suitability
suitable for matrix substance for MALDI-MS
storage temp.
2-8°C
Quality Level
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Related Categories
Application
- Hybrid Ethylcellulose Polymeric Films: Ag(I)-Based Components and Curcumin as Reinforcing Ingredients for Enhanced Food Packaging Properties: This research discusses the development of hybrid ethylcellulose films integrating curcumin to improve food packaging, emphasizing the analytical chemistry aspects like ingredient compatibility and performance evaluation (Crispini A et al., 2024).
- Intelligent double-layer film based on gellan gum/modified anthocyanin/curcumin/sodium alginate/zinc oxide for monitoring shrimp freshness: This article describes the creation of an intelligent film incorporating curcumin for real-time monitoring of shrimp freshness, showcasing a practical application of curcumin in food safety and shelf-life extension (Li C et al., 2024).
- Cyclodextrin-grafted redox-responsive hydrogel mediated by disulfide bridges for regulated drug delivery: This study examines a curcumin-incorporated cyclodextrin hydrogel, highlighting the use of curcumin in developing advanced drug delivery systems with potential applications in targeted therapy (Xu X et al., 2024).
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
Issac Abraham Sybiya Vasantha Packiavathy et al.
Food chemistry, 148, 453-460 (2013-11-23)
Urinary tract infection is caused primarily by the quorum sensing (QS)-dependent biofilm forming ability of uropathogens. In the present investigation, an anti-quorum sensing (anti-QS) agent curcumin from Curcuma longa (turmeric) was shown to inhibit the biofilm formation of uropathogens, such
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
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
Shahar Lev-Ari et al.
The Journal of nutritional biochemistry, 25(8), 843-850 (2014-05-20)
Non-small cell lung cancer (NSCLC) is the leading cause of cancer-related mortality. Curcumin is involved in various biological pathways leading to inhibition of NSCLC growth. The purpose of this study was to evaluate the effect of curcumin on expression of
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