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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:
12352205
NACRES:
NA.47
PubChem Substance ID:
MDL number:
Colour Index Number:
75300
Beilstein/REAXYS Number:
2306965
vapor density
13 (vs air)
Quality Level
assay
≥80% (Curcumin), ≥94% (curcuminoid content)
form
powder
mp
175 °C
solubility
ethanol: 1 mg/mL, DMSO: >11 mg/mL, 0.5 M NaOH: soluble (then immediately diluted in PBS)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
−20°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
Gene Information
human ... APP(351), CYP1A2(1544)
General description
Curcumin is a yellow colored polyphenol obtained from the rhizome of Curcuma longa L. It is also known as diferuloyl methane, a symmetric molecule with a seven carbon linker connecting two o-methoxy phenolic groups containing aromatic rings. Curcumin is synthesized by Pabon′s reaction using vanillin and acetyl acetone in the presence of boric oxide. It constitutes an important part of various diets and herbal medicines, especially in the Asian continent for its various salubrious effects on human health.
Application
Curcumin has been used:
- to study its in vitro effect on the inflammation and expression of tumour factor in patients with chronic kidney diseases
- to determine its influence when used in combination with high frequency ultrasound on human cervical carcinoma cells
- to study the possibility of using magnetic purification of curcumin from Curcuma longa by surface active maghemite nanoparticles (SAMNs)
- to examine its effect on the amyloid-β peptide levels along with the maturation of amyloid-β precursor proteins in various cell lines and primary cortical neurons in mouse
- as a supplement to evaluate its anti-carcinogenic and anti-apoptotic effect on cancer cells and cardiomyocytes
- to test its anti-inflammatory effect in human promyelocytic leukemia cell line, the HL-60
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.
Curcumin is postulated to have anti-depressant, anti-stress and neuroprotective effects on humans and other animals. Additionally, it also shows anti-fungal, antiviral, anti-microbial, chemosensitizing, radiosensitizing, and wound healing activities.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Assessment of herb-drug synergy to combat doxorubicin induced cardiotoxicity
Jain A and Rani V
Life Sciences, 205(3), 97-106 (2018)
The effect of turmeric extracts on inflammatory mediator production
Lantz RC, et al.
Phytomedicine, 12(6-7), 445-452 (2005)
The chemistry of curcumin: from extraction to therapeutic agent
Priyadarsini K
Molecules (Basel), 19(12), 20091-20112 (2014)