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B6938

Sigma-Aldrich

Bisdemethoxycurcumin

≥98% (HPLC), solid

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Synonym(s):
(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

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

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)

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Brazilian Curcuma longa L. attenuates comorbidities by modulating adipose tissue dysfunction in obese rats
Lo ATC, et al.
Nutrire, 43(1), 25-25 (2018)
Lahcen Tamegart et al.
Comptes rendus biologies, 342(5-6), 192-198 (2019-09-03)
Exposure to lead is a threat factor for neurodegenerative disorders progress as it could trigger dopaminergic deficiency. We aimed herein to assess the effect of acute lead exposure (25mg/kg B.W i.p.) during three continuous days on the dopaminergic and noradrenergic
Changjiang Luo et al.
Oncology letters, 9(1), 270-274 (2014-12-02)
Bisdemethoxycurcumin (BDMC) is a demethoxy derivative of curcumin. In this study, a human gastric adenocarcinoma xenograft model was generated in vivo using nude mice and BDMC was observed to suppress the growth and activity of tumors, in addition to improving
Wojciech Ostrowski
European journal of mass spectrometry (Chichester, England), 21(1), 45-50 (2015-04-24)
Curcumin complexes with iron ions were investigated by electrospray ionization mass spectrometry. It was shown that in methanol solutions of curcumin and iron(III) ions, complexes are formed with a stoichiometry of 1 : 1, 2 : or 3 : 1.
Meyliana Wulandari et al.
Analytical and bioanalytical chemistry, 407(3), 803-812 (2014-07-25)
This paper describes the synthesis of novel molecularly imprinted polymers (MIPs), prepared by a noncovalent imprinting approach, for cleanup and preconcentration of curcumin (CUR) and bisdemethoxycurcumin (BDMC) from medicinal herbal extracts and further analysis by high-performance liquid chromatography with fluorescence
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