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22608-11-3,MFCD03427310
Catalog No.:AA00BCHB

22608-11-3 | DEMETHOXYCURCUMIN

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1mg
≥98%
in stock  
$46.00   $32.00
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5mg
98% by HPLC
in stock  
$125.00   $88.00
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10mg
98% by HPLC
in stock  
$168.00   $117.00
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100mg
98%
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$226.00   $158.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BCHB
Chemical Name:
DEMETHOXYCURCUMIN
CAS Number:
22608-11-3
Molecular Formula:
C20H18O5
Molecular Weight:
338.3539
MDL Number:
MFCD03427310
SMILES:
COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
NSC Number:
687841
Properties
Computed Properties
 
Complexity:
502  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
7  
XLogP3:
3.3  

Upstream Synthesis Route

[1]JournalofNaturalProducts,1998,vol.61,#12,p.1531-1534

[1]JournalofNaturalProducts,1998,vol.61,#12,p.1531-1534

[1]JournalofNaturalProducts,1998,vol.61,#12,p.1531-1534

Literature

Title: Suppression effects of O-demethyldemethoxycurcumin on thapsigargin triggered on endoplasmic reticulum stress in SK-N-SH cells.

Journal: Neurotoxicology 20150901

Title: Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1.

Journal: Molecular nutrition & food research 20130901

Title: The cellular uptake and cytotoxic effect of curcuminoids on breast cancer cells.

Journal: Taiwanese journal of obstetrics & gynecology 20120901

Title: Isolation and identification of phase 1 metabolites of curcuminoids in rats.

Journal: Planta medica 20120801

Title: Effects of curcuminoids on frequency of acute myocardial infarction after coronary artery bypass grafting.

Journal: The American journal of cardiology 20120701

Title: Demethoxycurcumin inhibits cell proliferation, migration and invasion in prostate cancer cells.

Journal: Oncology reports 20120701

Title: Curcuminoids-loaded liposomes in combination with arteether protects against Plasmodium berghei infection in mice.

Journal: Experimental parasitology 20120701

Title: Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells.

Journal: Journal of natural medicines 20120401

Title: Metabolic and pharmacokinetic studies of curcumin, demethoxycurcumin and bisdemethoxycurcumin in mice tumor after intragastric administration of nanoparticle formulations by liquid chromatography coupled with tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110915

Title: Comparative absorption of a standardized curcuminoid mixture and its lecithin formulation.

Journal: Journal of natural products 20110425

Title: Reactions of reactive oxygen species (ROS) with curcumin analogues: Structure-activity relationship.

Journal: Free radical research 20110301

Title: Bisdemethoxycurcumin protects endothelial cells against t-BHP-induced cell damage by regulating the phosphorylation level of ERK1/2 and Akt.

Journal: International journal of molecular medicine 20110201

Title: Hypomethylation effects of curcumin, demethoxycurcumin and bisdemethoxycurcumin on WIF-1 promoter in non-small cell lung cancer cell lines.

Journal: Molecular medicine reports 20110101

Title: The inhibitory effects of different curcuminoids on β-amyloid protein, β-amyloid precursor protein and β-site amyloid precursor protein cleaving enzyme 1 in swAPP HEK293 cells.

Journal: Neuroscience letters 20101119

Title: Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity.

Journal: European journal of medicinal chemistry 20101001

Title: Anti-inflammatory mechanisms of compounds from Curcuma mangga rhizomes using RAW264.7 macrophage cells.

Journal: Natural product communications 20101001

Title: Curcuminoids enhance memory in an amyloid-infused rat model of Alzheimer's disease.

Journal: Neuroscience 20100901

Title: The inhibitory effect of turmeric curcuminoids on matrix metalloproteinase-3 secretion in human invasive breast carcinoma cells.

Journal: Archives of pharmacal research 20100701

Title: Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.

Journal: European journal of medicinal chemistry 20100301

Title: Demethoxycurcumin, a natural derivative of curcumin attenuates LPS-induced pro-inflammatory responses through down-regulation of intracellular ROS-related MAPK/NF-kappaB signaling pathways in N9 microglia induced by lipopolysaccharide.

Journal: International immunopharmacology 20100301

Title: Demethoxycurcumin suppresses migration and invasion of MDA-MB-231 human breast cancer cell line.

Journal: European journal of pharmacology 20100210

Title: Optimized turmeric extracts have potent anti-amyloidogenic effects.

Journal: Current Alzheimer research 20091201

Title: Metabolite analysis in Curcuma domestica using various GC-MS and LC-MS separation and detection techniques.

Journal: Biomedical chromatography : BMC 20090901

Title: Demethoxycurcumin induces Bcl-2 mediated G2/M arrest and apoptosis in human glioma U87 cells.

Journal: Biochemical and biophysical research communications 20090710

Title: Induction of antioxidant enzymes by curcumin and its analogues in human islets: implications in transplantation.

Journal: Pancreas 20090501

Title: A simple HPLC-fluorescence method for quantitation of curcuminoids and its application to turmeric products.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20090301

Title: Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA.

Journal: The Journal of nutritional biochemistry 20090201

Title: Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease.

Journal: Pharmacology, biochemistry, and behavior 20090201

Title: Direct analysis of curcumin in turmeric by DART-MS.

Journal: Phytochemical analysis : PCA 20090101

Title: Natural derivatives of curcumin attenuate the Wnt/beta-catenin pathway through down-regulation of the transcriptional coactivator p300.

Journal: Biochemical and biophysical research communications 20081226

Title: Comparison of inhibitory potency of three different curcuminoid pigments on nitric oxide and tumor necrosis factor production of rat primary microglia induced by lipopolysaccharide.

Journal: Neuroscience letters 20081205

Title: Demethoxycurcumin and its semisynthetic analogues as antitubercular agents.

Journal: Planta medica 20081201

Title: Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography.

Journal: Journal of pharmaceutical and biomedical analysis 20081104

Title: [Study on stability of curcumine, demethoxycurcumin and bisdemethoxycurcumin].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081101

Title: [Fingerprint of Curcuma phaeocaulis by LC-MS].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081001

Title: Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines.

Journal: Cancer chemotherapy and pharmacology 20080901

Title: Molecularly imprinted poly (methacrylamide-co-methacrylic acid) composite membranes for recognition of curcumin.

Journal: Analytica chimica acta 20080512

Title: Opposing effects of curcuminoids on serum stimulated and unstimulated angiogenic response.

Journal: Journal of cellular physiology 20080401

Title: Comparison of suppressive effects of demethoxycurcumin and bisdemethoxycurcumin on expressions of inflammatory mediators in vitro and in vivo.

Journal: Archives of pharmacal research 20080401

Title: [Study on effect of demethoxycurcumin in Curcuma long on stability of curcumin].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080401

Title: Regulation of heme oxygenase-1 expression by demethoxy curcuminoids through Nrf2 by a PI3-kinase/Akt-mediated pathway in mouse beta-cells.

Journal: American journal of physiology. Endocrinology and metabolism 20070901

Title: Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070901

Title: Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism.

Journal: Carcinogenesis 20070801

Title: Formulation and characterization of curcuminoids loaded solid lipid nanoparticles.

Journal: International journal of pharmaceutics 20070607

Title: Comparative study of copper(II)-curcumin complexes as superoxide dismutase mimics and free radical scavengers.

Journal: European journal of medicinal chemistry 20070401

Title: Curcuminoids, curcumin, and demethoxycurcumin reduce lead-induced memory deficits in male Wistar rats.

Journal: Journal of agricultural and food chemistry 20070207

Title: Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives.

Journal: Biological & pharmaceutical bulletin 20070101

Title: Comparative effects of curcuminoids on endothelial heme oxygenase-1 expression: ortho-methoxy groups are essential to enhance heme oxygenase activity and protection.

Journal: Experimental & molecular medicine 20060831

Title: [Effect of three different curcumin pigmens on the prdiferation of vascular smooth muscle cells by ox-LDL and the expression of LDL-R].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060301

Title: Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1).

Journal: Cancer chemotherapy and pharmacology 20060201

Title: Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.

Journal: Biochemical pharmacology 20050615

Title: Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice.

Journal: Journal of agricultural and food chemistry 20050223

Title: Detection and quantitation of curcumin in mouse lung cell cultures by matrix-assisted laser desorption ionization time of flight mass spectrometry.

Journal: Analytical biochemistry 20050201

Title: Antioxidative constituents of Etlingera elatior.

Journal: Journal of natural products 20050201

Title: Biochemical mechanism of modulation of human P-glycoprotein (ABCB1) by curcumin I, II, and III purified from Turmeric powder.

Journal: Biochemical pharmacology 20041115

Title: Modulation of human multidrug-resistance MDR-1 gene by natural curcuminoids.

Journal: BMC cancer 20040101

Title: Quantitative determination of curcuminoids in Curcuma rhizomes and rapid differentiation of Curcuma domestica Val. and Curcuma xanthorrhiza Roxb. by capillary electrophoresis.

Journal: Phytochemical analysis : PCA 20040101

Title: In vitro peroxynitrite scavenging activity of diarylheptanoids from Curcuma longa.

Journal: Phytotherapy research : PTR 20030501

Title: Microarray-based analysis of anti-angiogenic activity of demethoxycurcumin on human umbilical vein endothelial cells: crucial involvement of the down-regulation of matrix metalloproteinase.

Journal: Japanese journal of cancer research : Gann 20021201

Title: Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease.

Journal: Journal of natural products 20020901

Title: Curcuma longa extract supplementation reduces oxidative stress and attenuates aortic fatty streak development in rabbits.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20020701

Title: Improved HPLC method for the determination of curcumin, demethoxycurcumin, and bisdemethoxycurcumin.

Journal: Journal of agricultural and food chemistry 20020619

Title: Diarylheptanoids with free radical scavenging and hepatoprotective activity in vitro from Curcuma longa.

Journal: Planta medica 20011201

Title: Curcuminoids from Curcuma longa L. (Zingiberaceae) that protect PC12 rat pheochromocytoma and normal human umbilical vein endothelial cells from betaA(1-42) insult.

Journal: Neuroscience letters 20010427

Title: Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.

Journal: Journal of medicinal chemistry 19970912

Title: Somchit M, et al. Demethoxycurcumin from Curcuma longa rhizome suppresses iNOS induction in an in vitro inflamed human intestinal mucosa model. Asian Pac J Cancer Prev. 2014;15(4):1807-10.

Title: Wang X, et al. Effects of curcuminoids identified in rhizomes of Curcuma longa on BACE-1 inhibitory and behavioral activity and lifespan of Alzheimer's disease Drosophila models. BMC Complement Altern Med. 2014 Mar 5;14:88.

Title: Ko YC, et al. Demethoxycurcumin Alters Gene Expression Associated with DNA Damage, Cell Cycle and Apoptosis in Human Lung Cancer NCI-H460 Cells In Vitro. In Vivo. 2015 01-02;29(1):83-94.

Title: Katsidoni V, et al. Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit morphine's rewarding effect in rats. Psychopharmacology (Berl). 2014 Dec;231(23):4467-78.

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