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Chemical Structure| 33171-05-0 Chemical Structure| 33171-05-0

Structure of (E,E)-Bisdemethoxycurcumin
CAS No.: 33171-05-0

Chemical Structure| 33171-05-0

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Bisdemethoxycurcumin is a naturally occuring curcuminoid found in turmeric with anti-inflammatory properties.

Synonyms: (E,E)-Curcumin III; (E,E)-Didemethoxycurcumin; BDMC

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Product Details of (E,E)-Bisdemethoxycurcumin

CAS No. :33171-05-0
Formula : C19H16O4
M.W : 308.33
SMILES Code : O=C(CC(/C=C/C1=CC=C(O)C=C1)=O)/C=C/C2=CC=C(O)C=C2
Synonyms :
(E,E)-Curcumin III; (E,E)-Didemethoxycurcumin; BDMC
MDL No. :MFCD03419284
InChI Key :PREBVFJICNPEKM-YDWXAUTNSA-N
Pubchem ID :5315472

Safety of (E,E)-Bisdemethoxycurcumin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
HepG2 cells 5-1000μM 24, 48, 72 h To evaluate the inhibitory effect of BDMC on HepG2 cell proliferation, results showed that BDMC inhibited HepG2 cell proliferation in a time- and dose-dependent manner. Drug Des Devel Ther. 2020 Mar 5;14:993-1001
Peripheral blood mononuclear cells (PBMCs) 0.1 µM Overnight Enhanced phagocytosis of Aβ, up-regulated transcription of MGAT3 and TLRs, and translation of TLR2–4 Proc Natl Acad Sci U S A. 2007 Jul 31;104(31):12849-54
95D cells 5 µM 48 h BDMC suppressed TGF‑β1-induced EMT, as evidenced by the absence of mesenchymal-like morphological changes, no decrease in epithelial marker E-cadherin expression, and no increase in mesenchymal markers vimentin, fibronectin, and Snail expression. Chin Med J (Engl). 2015 May 20;128(10):1376-83

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
APP/PS1 transgenic mice Alzheimer's disease model Intravenous injection 5 mg/kg eq-BDMC Every 2 days for 2 weeks Evaluated therapeutic effects of St-Cl-Pr-BDMC-ANG in APP/PS1 mice, showing significant reduction in neurotoxic β-amyloid aggregate levels and improvement in olfactory memory and object recognition Sci Adv. 2021 Mar 26;7(13):eabf9180
ICR mice DSS-induced colitis model Dietary administration 0.1% and 0.5% 7-day treatment followed by a 14-day interval BDMC and CUR alleviated DSS-induced IBD in mice by strengthening tight junction proteins, reducing inflammatory cytokine secretion, and attenuating intestinal inflammatory protein expression. Furthermore, gut microbiota and short-chain fatty acid analyses revealed that CUR and BDMC effectively regulated gut microbial imbalance and promoted the relative abundance of butyrate-producing bacteria. J Agric Food Chem. 2025 Feb 12;73(6):3494-3506
BALBL/c nude mice H460 cell xenograft model Oral 100 mg/kg Once daily for 21 days The combination of BDMC and icotinib significantly inhibited the growth of H460 cell xenograft tumors through dual induction of autophagy and apoptosis. Int J Biol Sci. 2020 Mar 5;16(9):1536-1550.

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT01982734 Pharmacokinetics of New Curcum... More >>in Formulations Safety of New Curcumin Formulations Less << Early Phase 1 Completed - Germany ... More >> University of Hohenheim Stuttgart, Baden-Württemberg, Germany, 70599 Less <<
NCT02645656 Oral Submucous Fibrosis Phase 2 Unknown February 2016 India ... More >> SVS Institute of Dental Sciences, Mahabubnagar Hyderabad, Andhra Pradesh, India, 509002 Less <<
NCT03621865 Healthy Not Applicable Completed - France ... More >> Biofortis Mérieux NutriSciences Saint-Herblain, France, 44800 Less <<
NCT03530436 Safety After Oral Intake ... More >> Pharmacokinetics After Oral Intake Less << Not Applicable Completed - Germany ... More >> University of Hohenheim Stuttgart, Baden-Württemberg, Germany, 70599 Less <<
NCT01330810 Comparative Multidose Pharmaco... More >>kinetics Less << Phase 1 Completed - United States, North Carolina ... More >> UNC Department of Family Medicine Chapel Hill, North Carolina, United States, 27599 Less <<
NCT01925287 Pharmacokinetics of Novel Curc... More >>umin Formulations Safety of Novel Curcumin Formulations Less << Early Phase 1 Completed - Germany ... More >> University of Hohenheim Stuttgart, Germany, 70599 Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.24mL

0.65mL

0.32mL

16.22mL

3.24mL

1.62mL

32.43mL

6.49mL

3.24mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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