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Curcumin

CAT: 0013-GTR19161956-01Size: 1 gDry Ice: NoHazardous: No
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Description
Curcumin is a natural phenolic compound with impressive antioxidant properties. Curcumin is recently proved to exert its chemopreventive effects partly through the activation of nuclear factor (erythroid-2 related) factor 2 (Nrf2) . (In Vitro) :Curcumin exerts its chemopreventive effects partly through the activation of nuclear factor (erythroid-2 related) factor 2 (Nrf2) and its antioxidant and phase II detoxifying enzymes. Curcumin inhibits T47D cells growth, with IC50s of 25, 19 and 17.5 μM for 24, 48 and 72 h MTT assays respectively. IC50s of curcumin and silibinin mixture against T47D cells, are 17.5, 15, and 12 μM for 24, 48, and 72 h exposure times, respectively. Curcumin (2.5-80 μM) induces apoptotic cell death in AGS and HT-29 cell lines, and the IC50 is 21.9±0.1, 40.7±0.5 μM, respectively, in both AGS and HT-29 cell lines. Curcumin-induced apoptosis requires caspase activities in AGS and HT-29 cells. Curcumin induces ER Ca2+ decline and mitochondrial Ca2+ overloading. Curcumin induces the G2/M cell cycle arrest of LNCaP and PC-3 cells in a dose dependent manner. Curcumin upregulates the protein level of NF-kappaB inhibitor IkappaBalpha and downregulates protein levels of c-Jun and AR. (In Vivo) :Curcumin (10 mg/kg, p.o.) significantly prevents decrease in the percentage of sucrose consumption, as compared to the CMS-exposed rats. Curcumin treatment results in significant prevention of increase in TNF-α and IL-6 levels in stressed rats. Curcumin decreases binding of p300/CREB-binding protein (CBP) at the brain-derived neurotrophic factor (BDNF) promoter at 20 mg/kg (i.p.), reduces binding of P300/CBP at the BDNF promoter at 40 mg/kg, and decreases binding all the four proteins of p300/CBP and H3K9ac/H4K5ac at the BDNF promoter at 60 mg/kg in chronic constriction injury (CCI) rats.
CAS Number
458-37-7
Product Name Alternative
Indian Saffron | Turmeric yellow
Purity
>98% (HPLC)
Solubility
DMSO: 73mg/ml (198.16 mM) ; Water: <1mg/ml; Ethanol: <1mg/ml
Smiles
O=C (CC (/C=C/C1=CC=C (O) C (OC) =C1) =O) /C=C/C2=CC=C (O) C (OC) =C2
Molecular Formula
C21H20O6
Molecular Weight
368.39
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(1E,6E) -1,7-bis (4-hydroxy-3-methoxyphenyl) hepta-1,6-diene-3,5-dione

Chemical Information

Curcumin

Curcumin is a beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa. It has a role as a geroprotector, a metabolite, a biological pigment, an antineoplastic agent, a flavouring agent, an antifungal agent, a lipoxygenase inhibitor, a dye, an iron chelator, an EC 1.1.1.21 (aldehyde reductase) inhibitor, a radical scavenger, a contraceptive drug, an EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor, a nutraceutical, an immunomodulator, a ligand, an EC 1.1.1.205 (IMP dehydrogenase) inhibitor, an EC 3.5.1.98 (histone deacetylase) inhibitor, a hepatoprotective agent, a neuroprotective agent, an EC 1.8.1.9 (thioredoxin reductase) inhibitor, an anti-inflammatory agent, an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, a food colouring and an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor. It is a polyphenol, an aromatic ether, an enone, a beta-diketone and a diarylheptanoid. It is functionally related to a trans-ferulic acid.

CAS Number458-37-7
PubChem CID969516
IUPAC Name(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Molecular FormulaC21H20O6
Molecular Weight368.4
XLogP3.2
Topological Polar Surface Area93.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Heavy Atom Count27
Formal Charge0
Complexity507
SMILES
COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O
InChI
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
Chemical Structure
2D Structure
2D structure of Curcumin
CAS: 458-37-7
CID: 969516
Formula: C21H20O6
MW: 368.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight368.4
XLogP33.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass368.12598835
Monoisotopic Mass368.12598835
Topological Polar Surface Area93.1 Ų
Heavy Atom Count27
Formal Charge0
Complexity507
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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