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458-37-7 (Curcumin)

1

Identification

Curcumin Curcumin
Name Curcumin
Formula C21H20O6
MW 368.38
CAS No. 458-37-7
EINECS 207-280-5
Smiles OC1=C(OC)C=C(/C=C/C(CC(/C=C/C2=CC(OC)=C(O)C=C2)=O)=O)C=C1
Synonyms 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; C.I. 75300; C.I. Natural Yellow 3; Diferuloylmethane; (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
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+
2

Introduction

Curcumin is a natural phenolic compound with impressive antioxidant properties.

Background Information

Anti-cancer compound. Interferes with multiple cell signaling pathways, including cell cycle (cyclin D1 and cyclin E), apoptosis (activation of caspases and down-regulation of anti-apoptotic gene products), proliferation (HER-2, EGFR and AP-1), survival (PI3K/AKT pathway), invasion (MMP-9 and adhesion molecules), angiogenesis (VEGF), metastasis (CXCR-4) and inflammation (NF-κB, TNF, IL-6, IL-1, COX-2 and 5-LOX). Anti-angiogenic. Anti-metastatic. Anti-invasive. Chemopreventive. Sonic hedgehog (Shh) signaling pathway modulator. Downregulates Shh and Gli1. Antioxidant. Anti-inflammatory. Potent inhibitor of NF-κB, cyclooxygenase-2 (COX-2), lipooxygenase (LOX), and inducible nitric oxide synthase (iNOS; NOSII). Downregulates the expression of various proinflammatory cytokines including TNF, IL-1, IL-2, IL-6, IL-8, IL-12 and chemokines. Potent immunomodulator. Modulates several key transcription factors. Down-regulate transcription factors NF-κB, AP-1 and Egr-1. Down-regulates the expression of COX-2, LOX, NOS, MMP-9, uPA, TNF, chemokines, cell surface adhesion molecules and cyclin D1. Down-regulate growth factor receptors (such as EGFR and HER2) and inhibits the activity of c-Jun N-terminal kinase, protein tyrosine kinases and protein serine/threonine kinases. Neuroprotective. Anti-amyloid activity. Cardioprotective. p300/CBP-HAT inhibitor. Regulates lipid metabolism and downregulates obesity. Activates peroxisome proliferator-activated receptor-γ (PPARγ) and Nrf2 cell-signaling pathways. Antiviral, antibacterial, antifungal. Epigenetic agent. Interacts with histone deacetylases (HDACs), histone acetyltransferases (HATs), DNA methyltransferase I and microRNAs. Proteasome modulator/inhibitor. Inducer of autophagy in lung adenocarcinoma cells. ......by Adipogen Corporation
Curcumin is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family (Zingiberaceae). ......by BOC Sciences
Cell-permeable. An antioxidant and dual inhibitor of 5-lipoxygenase (IC₅₀ = 8 µM) and cyclooxygenase (COX) (IC₅₀ = 52 µM). Also inhibits glutathione S-transferase, induction of nitric oxide (NO) in activated macrophages and inhibits EGF-induced tyrosine phosphorylation of EGF receptors. Also shown to be a p300/CREB-binding protein-specific inhibitor of histone acetyltransferase, inhibiting the acetylation of histones H3 and H4 with an IC₅₀ of ~25 µM. Does not affect p300/CREB binding protein-associated factor (PCAF). ......by BioVision, Inc.,
Curcumin is a natural phenolic compound with impressive antioxidant properties, acts as a p300/CREB-binding protein inhibitor of histone acetyltransferase activity, and also activates nuclear factor (erythroid-2 related) factor 2 (Nrf2). ......by MedChemexpress Co., Ltd.
Curcumin is a diarylheptanoid. It is the principal curcuminoid of turmeric, which is a member of the ginger family (Zingiberaceae). Turmeric's other two curcuminoids are desmethoxycurcumin and bis-desmethoxycurcumin. Curcumin is a bright-yellow color and may be used as a food coloring. As a food additive, its E number is E100. A survey of the literature shows a number of potential effects under study and that daily doses over a 3-month period of up to 12 grams were safe. Clinical trials in humans are studying the effect of curcumin on various diseases, including multiple myeloma, pancreatic cancer, myelodysplastic syndromes, colon cancer, psoriasis, arthritis, major depressive disorder and Alzheimer's disease. ......by MedKoo Biosciences, Inc.
Curcumin is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family (Zingiberaceae). It is an inhibitor of p300 histone acetylatransferase(IC50~25 μM) and Histone deacetylase; activates Nrf2 pathway and supresses the activation of transcription factor NF-κB. ......by Selleck Chemicals LLC
A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes. ......by Target Molecule Corp.
Antitumor, anti-inflammatory and antioxidant agent. Downregulates expression of reactive-oxygen-generating enzymes (cyclooxygenase, lipoxygenase, iNOS), TNFα, IL-1, IL-6, PKC, EGFR, NF-κB, IκB kinase and more. Upregulates expression of PPARγ, p53, Nrf2. Also displays antimicrobial, antidiabetic neuro- and cardioprotective properties in vivo. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Cell lines murine melanoma cell subline(B16-R)
Conditions 0-100 μM; 24-48 h
Method 1×104 B16-R cells are cultivated as monolayer culture for 12 hr. They were then incubated in 200 μL of RPMI, 10% FBS containing curcumin at final concentrations from 1–100 μM in 96-multiwell plates for 24-48 hr. After these incubations, cells are washed twice in PBS and 500 μl of fresh culture medium containing MTT (0.3 mg/mL) are added for colorimetric assay.
Source Selleck Chemicals LLC

Animal Experiment

Animal Models Female B6D2F1 mice (6-8 weeks old)
Dosage 25 mg/kg
Formulation Dissolved in DMSO and diluted with 0.85% NaCl
Administration i.p.
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:Light yellow to yellow Solid EBNumber:EB000016976

Storage condition

Store at -20°C by Tocris Bioscience Inc.

Solubility

DMSO by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 74 mg/mL (200.87 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM); In vivo 10% DMSO+50% PEG 300+ddH2O40mg/mL by Selleck Chemicals LLC
Soluble to 10 mM in DMSO and to 5 mM in ethanol by Tocris Bioscience Inc.
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Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Curcumin Beersheva Mental Health Center Depression 2010/8/31 2011/6/30 Phase 4 Clinical
Curcumin Instituto Nacional de Cardiologia Ignacio Chavez End stage renal disease 2013/2/28 2013/11/30 Phase 3 Clinical
Curcumin Mahidol University Lebers hereditary optic atrophy 2005/5/31 2007/12/31 Phase 3 Clinical
Curcumin Tel Aviv Sourasky Medical Center Colon tumor 2006/3/31 2007/3/31 Phase 3 Clinical
Curcumin Tel Aviv Sourasky Medical Center Pancreas tumor 2005/6/30 Phase 3 Clinical
Curcumin - Phase 1 Clinical
Curcumin - Phase 4
7

Safety Data of Curcumin

Hazard Symbols : Xi
Risk Statements : R36/37/38
Safety Statements : S26;S36
HS Code : 29145000
RTECS : MI5230000
WGKGermany : 2
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Spectral Information

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Suppliers List

10

Related Products

Other Forms of 458-37-7

Name CAS No Formula MW

Recommended Compounds in Keap1-Nrf2 Autophagy

Name CAS No Formula MW
CDDO-EA 932730-51-3 C33H46N2O3 518.73
RTA-408 1474034-05-3 C33H44F2N2O3 554.7108664
Isoalantolactone 470-17-7 C15H20O2 232.32
Gypenoside XVII 80321-69-3 C48H82O18 947.15
Nordihydroguaiaretic acid 500-38-9 C18H22O4 302.36
Ezetimibe 163222-33-1 C24H21F2NO3 409.43
Dimethyl fumarate 624-49-7 C6H8O4 144.13
Bardoxolone 218600-44-3 C31H41NO4 491.66
Bardoxolone (methyl) 218600-53-4 C32H43NO4 505.69
Hinokitiol 499-44-5 C10H12O2 164.2
NK-252 1414963-82-8 C13H11N5O3 285.2581
Ezetimibe D4 1093659-90-5 C24H17D4F2NO3 413.45
Danshensu 76822-21-4 C9H10O5 198.17
ML385 846557-71-9 C31H29N3O2S 507.65
Cpd16 C24H22N2O6S2 498.57
Cpd16-AA C28H26N2O10S2 614.64
TBE-31 936475-62-6 C21H18N2O2 330.38
AEM1 1030123-90-0 C20H14FN3O2S 379.41
Lyngbyabellin A 273202-85-0 C29H40Cl2N4O7S2 691.69
Grassypeptolide A 1010433-25-6 C56H79N9O10S2 1102.41

Recommended Compounds in Same Indication

Name CAS No Formula MW
Iloperidone 133454-47-4 C24H27FN2O4 426.48
Tianeptine 72797-41-2 C21H25ClN2O4S 436.95
Cariprazine 839712-12-8 C21H32Cl2N4O 427.41
Asenapine 65576-45-6 C17H16ClNO 285.77
Asenapine (maleate) 85650-56-2 C21H20ClNO5 401.84
LY2603618 911222-45-2 C18H22BrN5O3 436.3
Bardoxolone 218600-44-3 C31H41NO4 491.66
Bardoxolone (methyl) 218600-53-4 C32H43NO4 505.69
Axitinib 319460-85-0 C22H18N4OS 386.47
Cinacalcet (hydrochloride) 364782-34-3 C22H23ClF3N 393.87
Aleglitazar (racemate) 475479-24-4 C24H23NO5S 437.5081
Vortioxetine 508233-74-7 C18H22N2S 298.45
RO4929097 847925-91-1 C22H20F5N3O3 469.4
5-Fluorouracil 51-21-8 C4H3FN2O2 130.08
Rolipram 61413-54-5 C16H21NO3 275.34
Oxaliplatin 61825-94-3 C8H14N2O4Pt 397.29
Cinacalcet 226256-56-0 C22H22F3N 357.41
Zolpidem 82626-48-0 C19H21N3O 307.39
Calcitriol 32222-06-3 C27H44O3 416.64
Calcifediol (monohydrate) 63283-36-3 C27H44O2 400.64
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Route of Synthesis

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References

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More Information

Curcumin

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