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Bisdemethoxycurcumin

Alias: Bisdemethoxycurcumin; Curcumin III
Cat No.:V30880 Purity: ≥98%
(E,E)-Bisdemethoxycurcumin ((E,E)-Curcumin III) is a curcumin analogue with anti~inflammatory and anticancer activities.
Bisdemethoxycurcumin
Bisdemethoxycurcumin Chemical Structure CAS No.: 33171-05-0
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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Other Forms of Bisdemethoxycurcumin:

  • Bisdemethoxycurcumin-d8 (Curcumin III-d8; Didemethoxycurcumin-d8)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
(E,E)-Bisdemethoxycurcumin ((E,E)-Curcumin III) is a curcumin analogue with anti~inflammatory and anticancer activities.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Bisdemethoxycurcumin (BDMC) is a demethoxy derivative of curcumin, which is a natural substance found in the turmeric root. In a dose-dependent manner, BDMC slows the growth of the SGC 7901 gastric cancer cells. Since BDMC prevents cells from progressing to S phase and finishing the cycle, cell growth is stopped in G1 phase[2].
ln Vivo
Through modulating mitochondria, BDMC may encourage tumor apoptosis. In a xenograft model of gastric adenoadenocarcinoma, BDMC inhibits tumor growth and increases body weight[2].
Enzyme Assay
The cells are grown in a humid environment with 5% CO2 at 37°C. As a positive control, DAC is used to assess the hypomethylation effect of bisdemethoxycurcumin. Before use, stock solutions of curcumin, DMC, BDMC, and DAC (20 mM) in dimethyl sulfoxide (DMSO) are prepared and diluted in sterile-filtered media. In 6-well culture plates, 1×105 cells are seeded. Following a 24-hour culture period, the cells are given a 72-hour treatment with curcumin, DMC, BDMC (0-100 μM) or DAC (20 μM).
References

[1]. Mol Med Rep . 2011 Jul-Aug;4(4):675-9.

[2]. Oncol Lett . 2015 Jan;9(1):270-274.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₉H₁₆O₄
Molecular Weight
308.33
Exact Mass
308.10485899
CAS #
33171-05-0
Related CAS #
Bisdemethoxycurcumin-d8;2470233-08-8
Appearance
Solid
SMILES
C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
InChi Key
PREBVFJICNPEKM-YDWXAUTNSA-N
InChi Code
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+
Chemical Name
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Synonyms
Bisdemethoxycurcumin; Curcumin III
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~62 mg/mL (201.1 mM)
Ethanol: ~25 mg/mL (~81.1 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2433 mL 16.2164 mL 32.4328 mL
5 mM 0.6487 mL 3.2433 mL 6.4866 mL
10 mM 0.3243 mL 1.6216 mL 3.2433 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Tumor volumes of xenograft model on nude mice in control and BDMC groups. *P<0.05 and **P<0.01. BDMC, bisdemethoxycurcumin. Oncol Lett . 2015 Jan;9(1):270-274.
  • Cell viability detections in control and BDMC groups. *P<0.05 and **P<0.01. BDMC, bisdemethoxycurcumin; OD, optical density. Oncol Lett . 2015 Jan;9(1):270-274.
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