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33171-05-0,MFCD03419284
Catalog No.:AA003BCO

33171-05-0 | Bisdemethoxycurcumin

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1mg
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10mg
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25mg
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50mg
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250mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003BCO
Chemical Name:
Bisdemethoxycurcumin
CAS Number:
33171-05-0
Molecular Formula:
C19H16O4
Molecular Weight:
308.3279
MDL Number:
MFCD03419284
SMILES:
O=C(CC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O
NSC Number:
687839
Properties
Properties
 
BP:
551.3°C at 760 mmHg  
Form:
Solid  
MP:
221-223 °C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
408  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
6  
XLogP3:
3.3  

Literature

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

Journal: Molecular nutrition & food research 20130901

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Curcumin is an inhibitor of calcium/calmodulin dependent protein kinase II.

Journal: Bioorganic & medicinal chemistry 20121015

Title: Evaluation in vitro of synthetic curcumins as agents promoting monocytic gene expression related to β-amyloid clearance.

Journal: Chemical research in toxicology 20120113

Title: Structural investigation into the inhibitory mechanisms of indomethacin and its analogues towards human glyoxalase I.

Journal: Bioorganic & medicinal chemistry letters 20110715

Title: Significant enhancement in radical-scavenging activity of curcuminoids conferred by acetoxy substituent at the central methylene carbon.

Journal: Bioorganic & medicinal chemistry 20110615

Title: Identification of curcumin derivatives as human glyoxalase I inhibitors: A combination of biological evaluation, molecular docking, 3D-QSAR and molecular dynamics simulation studies.

Journal: Bioorganic & medicinal chemistry 20110201

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

Journal: European journal of medicinal chemistry 20101001

Title: An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.

Journal: Journal of natural products 20100723

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

Journal: European journal of medicinal chemistry 20100301

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

Journal: Current Alzheimer research 20091201

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

Journal: Pancreas 20090501

Title: Comparative antiulcer effect of bisdemethoxycurcumin and curcumin in a gastric ulcer model system.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20090401

Title: Structure-activity relationship studies of curcumin analogues.

Journal: Bioorganic & medicinal chemistry letters 20090401

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: Curcumin is a potent DNA hypomethylation agent.

Journal: Bioorganic & medicinal chemistry letters 20090201

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

Journal: Cancer chemotherapy and pharmacology 20080901

Title: Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS.

Journal: Molecular nutrition & food research 20080901

Title: Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors.

Journal: Bioorganic & medicinal chemistry 20080901

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: Immune defects in Alzheimer's disease: new medications development.

Journal: BMC neuroscience 20080101

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

Journal: Cancer chemotherapy and pharmacology 20060201

Title: Efficiency of foam fractionation for the enrichment of nonpolar compounds from aqueous extracts of plant materials.

Journal: Journal of natural products 20050901

Title: A labdane diterpene glucoside from the rhizomes of Curcuma mangga.

Journal: Journal of natural products 20050701

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

Journal: Biochemical pharmacology 20050615

Title: Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents.

Journal: Bioorganic & medicinal chemistry letters 20050401

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

Journal: Biochemical pharmacology 20041115

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

Journal: Phytotherapy research : PTR 20030501

Title: Studies on the role of some synthetic curcuminoid derivatives in the inhibition of tumour specific angiogenesis.

Journal: Journal of experimental & clinical cancer research : CR 20030301

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: CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site.

Journal: Journal of medicinal chemistry 20020214

Title: Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.

Journal: Journal of medicinal chemistry 19981008

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: Lee PJ, et al. Bisdemethoxycurcumin Induces Apoptosis in Activated Hepatic Stellate Cells via Cannabinoid Receptor 2. Molecules. 2015 Jan 14;20(1):1277-92.

Title: Chen J, et al. Natural borneol enhances bisdemethoxycurcumin-induced cell cycle arrest in the G2/M phase through up-regulation of intracellular ROS in HepG2 cells. Food Funct. 2014 Dec 24.

Title: Luo C, et al. Bisdemethoxycurcumin attenuates gastric adenocarcinoma growth by inducing mitochondrial dysfunction. Oncol Lett. 2015 Jan;9(1):270-274.

Title: Li YB, et al. Bisdemethoxycurcumin Increases Sirt1 to Antagonize t-BHP-Induced Premature Senescence in WI38 Fibroblast Cells. Evid Based Complement Alternat Med. 2013;2013:851714.

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