(E,E)-Bisdemethoxycurcumin ((E,E)-Curcumin III) is a curcumin analogue with anti~inflammatory and anticancer activities.

Physicochemical Properties

Molecular Formula	C₁₉H₁₆O₄
Molecular Weight	308.33
Exact Mass	308.104
CAS #	33171-05-0
Related CAS #	Bisdemethoxycurcumin-d8;2470233-08-8
PubChem CID	5315472
Appearance	Yellow to orange solid
Density	1.3±0.1 g/cm3
Boiling Point	551.3±45.0 °C at 760 mmHg
Melting Point	221-223ºC
Flash Point	301.3±25.2 °C
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.680
LogP	3.39
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Heavy Atom Count	23
Complexity	408
Defined Atom Stereocenter Count	0
SMILES	OC1C=CC(=CC=1)/C=C/C(CC(/C=C/C1=CC=C(C=C1)O)=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)

Biological Activity

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).
ADME/Pharmacokinetics	Metabolism / Metabolites Bisdemethoxycurcumin has known human metabolites that include Bisdemethoxycurcumin, 4-O-glucuronide.
References	[1]. Mol Med Rep . 2011 Jul-Aug;4(4):675-9. [2]. Oncol Lett . 2015 Jan;9(1):270-274.
Additional Infomation	Bisdemethoxycurcumin is a beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups. It has a role as a metabolite and an EC 3.2.1.1 (alpha-amylase) inhibitor. It is a beta-diketone, a polyphenol, an enone and a diarylheptanoid. It is functionally related to a 4-coumaric acid. Bisdemethoxycurcumin has been reported in Curcuma xanthorrhiza, Curcuma kwangsiensis, and other organisms with data available.

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.