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B6938 Sigma-Aldrich

Bisdemethoxycurcumin

≥98% (HPLC), solid

Synonym: (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

  • Empirical Formula (Hill Notation) C19H16O4

  • Molecular Weight 308.33

  •  MDL number MFCD03419284

  •  PubChem Substance ID 329773290

  •  NACRES NA.77

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Properties

Related Categories B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology
Quality Level   100
assay   ≥98% (HPLC)
form   solid
solubility   DMSO: ≥20 mg/mL
storage temp.   2-8°C
SMILES string   Oc1ccc(cc1)\C=C\C(=O)CC(=O)\C=C\c2ccc(O)cc2
InChI   1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
InChI key   PREBVFJICNPEKM-YDWXAUTNSA-N

Description

Application

Bisdemethoxycurcumin has been used:
• to test its inhibitory effect on cell cycle and mitochondrial function in gastric adenocarcinoma cells
• to test it neuroprotective role against lead (Pb) induced toxicity in dopaminergic and noradrenergic systems of Meriones shawi
• as a standard for calibration curve generation to quantify plasma curcuminoids using high-performance liquid chromatography-diode array detection (HPLC-DAD) and ultraviolet (UV)

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Bisdemethoxycurcumin (BDMC) is a derivative or curcumin, and represents one of the major active components of curcumin products isolated from Curcumae sp. BDMC shares similar anti-inflammatory properties with demethoxycurcumin. It inhibits LPS-induced nitric oxide (NO) production and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. BDMC also displays unique properties in that it enhances Abeta clearance by upregulating expression MGAT3 and TLR genes. BDMC potently inhibits AKR1B10.

Bisdemethoxycurcumin (BMDC) is a stable dimethoxy derivative of curcumin and is useful as a supplement in cell culture medium. It also possesses antimicrobial, antioxidative and neuroprotective functionality.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Central Nervous System, Diseases, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions

Peer-Reviewed Papers
15

References

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