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Curcumin

CAT: 0804-HY-N0005-04Size: 1 gDry Ice: NoHazardous: No
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CAT#:0804-HY-N0005-04Size:1 g
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Description
Curcumin (Diferuloylmethane), a natural phenolic compound, is a p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription. Curcumin is a photosensitizer against microorganisms. Curcumin shows inhibitory effects on NF-κB and MAPKs, and has diverse pharmacologic effects including anti-inflammatory, antioxidant, antiproliferative and antiangiogenic activities. Curcumin induces stabilization of Nrf2 protein through Keap1 cysteine modification.
CAS Number
458-37-7
Product Name Alternative
Diferuloylmethane; Natural Yellow 3; Turmeric yellow
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Autophagy; Epigenetic Reader Domain; Ferroptosis; Histone Acetyltransferase; Influenza Virus; Keap1-Nrf2; Mitophagy
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Autophagy; Epigenetics; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection; Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/Curcumin.html
Purity
98.84
Solubility
DMSO : 100 mg/mL (ultrasonic)
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
368.38
Precautions
H302, H315, H319, H335
References & Citations
[1]Gao S, et al. Curcumin attenuates arsenic-induced hepatic injuries and oxidative stress in experimental mice through activation of Nrf2 pathway, promotion of arsenic methylation and urinary excretion. Food Chem Toxicol. 2013 Jul 18. pii: S0278-6915 (13) 004|[2]Nasiri M, et al. Curcumin and Silibinin Inhibit Telomerase Expression in T47D Human Breast Cancer Cells. Asian Pac J Cancer Prev. 2013;14 (6) :3449-53.|[3]Cao A, et all. Curcumin induces apoptosis in human gastric carcinoma AGS cells and colon carcinoma HT-29 cells through mitochondrial dysfunction and endoplasmic reticulum stress. Apoptosis. 2013 Jul 24. [Epub ahead of print]|[4]Jiang H, et al. Antidepressant-like effects of curcumin in chronic mild stress of rats: Involvement of its anti-inflammatory action. Prog Neuropsychopharmacol Biol Psychiatry. 2013 Jul 20. pii: S0278-5846 (13) 00150-4.|[5]Guo H, et al. Curcumin induces cell cycle arrest and apoptosis of prostate cancer cells by regulating the expression of IkappaBalpha, c-Jun and androgen receptor. Pharmazie. 2013 Jun;68 (6) :431-4.|[6]Zhu X, et al. Curcumin alleviates neuropathic pain by inhibiting p300/CBP histone acetyltransferase activity-regulated expression of BDNF and cox-2 in a rat model. PLoS One. 2014 Mar 6;9 (3) :e91303.|[7]Balasubramanyam K, et al. Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription. J Biol Chem. 2004 Dec 3;279 (49) :51163-71.|[8]Jun Wan Shin, et al. Curcumin induces stabilization of Nrf2 protein through Keap1 cysteine modification. Biochem Pharmacol. 2020 Mar;173:113820.|[9]Lucas D. Dias, et al. Curcumin as a photosensitizer: From molecular structure to recent advances in antimicrobial photodynamic therapy. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. Volume 45, December 2020, 100384.|[10]Jiang E, et al. Curcumin Inhibits Oxidative Stress and Apoptosis Induced by H2O2 in Bovine Adipose-Derived Stem Cells (bADSCs) . Animals (Basel) . 2024 Nov 26;14 (23) :3421.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Phase 4
Isoform
CBP/p300

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...
View on PubChemRaw 3D data
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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