Art. -Nr.: HY-N0007

(E,E)-Bisdemethoxycurcumin

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

4 Cited Publications

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Based on 4 publication(s) in Google Scholar

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

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Reinheit: 98.63%
CAS. Nr.: 33171-05-0
Formel: C₁₉H₁₆O₄
Molecular Weight:308.33

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

(E,E)-Bisdemethoxycurcumin Chemical Structure

CAS. Nr.: 33171-05-0

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (4)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

(E,E)-Bisdemethoxycurcumin ((E,E)-Curcumin III) is a curcumin derivative with anti-inflammatory and anticancer activities^[1]^[2]^[3]^[4]^[5]^[6].

Cellular Effect

Cell Line	Type	Value	Description	References
A-431	IC₅₀	>100 μM Compound: BDC	Cytotoxicity against human A431 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay Cytotoxicity against human A431 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	[PMID: 29605808]
A549	IC₅₀	38.1 μM Compound: Bisdemethoxycurcumin	Cytotoxicity against human A549 cells after 72 hrs by crystal violet staining based microplate reader analysis Cytotoxicity against human A549 cells after 72 hrs by crystal violet staining based microplate reader analysis	[PMID: 23153397]
Caco-2	IC₅₀	>100 μM Compound: 1b	Cytotoxicity against human Caco2 cells assessed as decrease in cell viability after 48 hrs by MTT assay Cytotoxicity against human Caco2 cells assessed as decrease in cell viability after 48 hrs by MTT assay	[PMID: 27843113]
Caco-2	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of differentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay Growth inhibition of differentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	[PMID: 27521589]
CHO-K1	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of CHOK1 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay Growth inhibition of CHOK1 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	[PMID: 27521589]
CHO-K1	IC₅₀	91.4 μM Compound: 1b	Cytotoxicity against CHOK1 cells assessed as decrease in cell viability after 48 hrs by MTT assay Cytotoxicity against CHOK1 cells assessed as decrease in cell viability after 48 hrs by MTT assay	[PMID: 27843113]
DLD-1	IC₅₀	>40 μM Compound: BDC	Cytotoxicity against human DLD1 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay Cytotoxicity against human DLD1 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	[PMID: 29605808]
DU-145	IC₅₀	30.1 μM Compound: bisdemethoxycurcumin	Cytotoxicity against human DU145 Cytotoxicity against human DU145	[PMID: 16038556]
EA.hy 926	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of human EAhy926 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay Growth inhibition of human EAhy926 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	[PMID: 27521589]
EA.hy 926	IC₅₀	54.3 μM Compound: 1b	Cytotoxicity against human EAhy926 cells assessed as decrease in cell viability after 48 hrs by MTT assay Cytotoxicity against human EAhy926 cells assessed as decrease in cell viability after 48 hrs by MTT assay	[PMID: 27843113]
EOL1	IC₅₀	22.3 μM Compound: 4	Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay	[PMID: 24689857]
HEK293	EC₅₀	200 μM Compound: 3	Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay	[PMID: 20004045]
HepG2	IC₅₀	>100 μM Compound: 1b	Cytotoxicity against human HepG2 cells assessed as decrease in cell viability after 48 hrs by MTT assay Cytotoxicity against human HepG2 cells assessed as decrease in cell viability after 48 hrs by MTT assay	[PMID: 27843113]
HepG2	IC₅₀	>50 μM Compound: bisdemethoxycurcumin	Cytotoxicity against human HepG2 Cytotoxicity against human HepG2	[PMID: 16038556]
HepG2	IC₅₀	62.9 μM Compound: Bisdemethoxycurcumin	Cytotoxicity against human HepG2 cells after 72 hrs by crystal violet staining based microplate reader analysis Cytotoxicity against human HepG2 cells after 72 hrs by crystal violet staining based microplate reader analysis	[PMID: 23153397]
HepG2	IC₅₀	75.5 μM Compound: 1c	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 26894841]
HL-60	IC₅₀	25.12 μM Compound: bisdemethoxycurcumin	Cytotoxicity against human HL60 Cytotoxicity against human HL60	[PMID: 16038556]
HT-1080	IC₅₀	7 μM Compound: BDMC	Decrease in UPA expression in human HT1080 cells Decrease in UPA expression in human HT1080 cells	[PMID: 31336310]
HT-29	IC₅₀	>100 μM Compound: 1b	Cytotoxicity against human HT-29 cells assessed as decrease in cell viability after 48 hrs by MTT assay Cytotoxicity against human HT-29 cells assessed as decrease in cell viability after 48 hrs by MTT assay	[PMID: 27843113]
HT-29	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of human HT-29 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay Growth inhibition of human HT-29 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	[PMID: 27521589]
KB	CC₅₀	8.5 μM Compound: 11c	Compound concentration required to reduce the exponential growth of KB cells by 50% Compound concentration required to reduce the exponential growth of KB cells by 50%	[PMID: 9767632]
KB	IC₅₀	21.44 μM Compound: 3	Cytotoxicity against human KB cells assessed as growth inhibition by resazurin microplate assay Cytotoxicity against human KB cells assessed as growth inhibition by resazurin microplate assay	[PMID: 24857542]
LNCaP	IC₅₀	19.7 μM Compound: 2	Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay	[PMID: 19249204]
MCF7	IC₅₀	24.3 μM Compound: 2	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	[PMID: 19249204]
MCF7	IC₅₀	33.78 μM Compound: bisdemethoxycurcumin	Cytotoxicity against human MCF7 Cytotoxicity against human MCF7	[PMID: 16038556]
MCF7	IC₅₀	48.9 μM Compound: BDC	Cytotoxicity against human MCF7 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay Cytotoxicity against human MCF7 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	[PMID: 29605808]
MDA-MB-231	IC₅₀	11 mM Compound: BDMC	Increase in MMP3 level in human MDA-MB-231 cells after 24 hrs by ELISA Increase in MMP3 level in human MDA-MB-231 cells after 24 hrs by ELISA	[PMID: 31336310]
MDA-MB-231	IC₅₀	21.9 μM Compound: 2	Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay	[PMID: 19249204]
MDA-MB-231	IC₅₀	24 μM Compound: bisdemethoxycurcumin	Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated 4 hrs before TGF-beta challenge measured after 24 hrs by radioimmunoassay Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated 4 hrs before TGF-beta challenge measured after 24 hrs by radioimmunoassay	[PMID: 23145932]
MDA-MB-231	IC₅₀	38.5 μM Compound: Bisdemethoxycurcumin	Cytotoxicity against human MDA-MB-231 cells after 72 hrs by crystal violet staining based microplate reader analysis Cytotoxicity against human MDA-MB-231 cells after 72 hrs by crystal violet staining based microplate reader analysis	[PMID: 23153397]
MT4	CC₅₀	13 μM Compound: 11c	Compound concentration required to reduce the exponential growth of MT-4 cells by 50% Compound concentration required to reduce the exponential growth of MT-4 cells by 50%	[PMID: 9767632]
NCI-H460	IC₅₀	88.1 μM Compound: bisdemethoxycurcumin	Cytotoxicity against human NCI-H460 Cytotoxicity against human NCI-H460	[PMID: 16038556]
PC-12	ED₅₀	2 μg/mL Compound: 5, bisdemethoxycurcumin	Protection against beta-amyloid (25 to 35) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay Protection against beta-amyloid (25 to 35) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay	[PMID: 12350137]
PC-12	ED₅₀	3.5 μg/mL Compound: 5, bisdemethoxycurcumin	Protection against beta-amyloid (1 to 42) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay Protection against beta-amyloid (1 to 42) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay	[PMID: 12350137]
PC-3	IC₅₀	27.3 μM Compound: 2	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	[PMID: 19249204]
WRL68	IC₅₀	45.4 μM Compound: BDC	Cytotoxicity against human WRL68 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay Cytotoxicity against human WRL68 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay	[PMID: 29605808]

In Vitro

Bisdemethoxycurcumin (1-10 μM; 5 h) significantly inhibits HT1080 cancer cell invasion, but does not affect cell migration^[5].
Bisdemethoxycurcumin (1-10 μM; 24 h) inhibits the secret of MMP-9 in HT1080 cells, and affects cancer cell invasion and metastasis^[5].
Bisdemethoxycurcumin (5-50 μM; 24 h) Bisdemethoxycurcumin (5-50 μM; 24 h) significantly inhibits collagenase, MMP-2 and MMP-9 activities in HT1080, but does not inhibit uPA activity^[5].
Bisdemethoxycurcumin (25 μM; 18 h, 24 h) arrests cell cycle at G1 phase, and (5-25 μM) inhibits the expression of C/EBPα and PPARγ in 3T3-L1 adipocyte 270 differentiation^[6].
Bisdemethoxycurcumin inhibits lipid accumulation in adipocytes, primarily by attenuating mitotic clonal expansion (MCE) to inhibit early lipogenesis^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Bisdemethoxycurcumin (0.5% in diet; 15 weeks) significantly reduces both final body weight and body weight gain in HFD-induced obese mice^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS. Nr. 33171-05-0
Appearance Solid
Molecular Weight 308.33
Formel C₁₉H₁₆O₄
Color Yellow to orange
SMILES

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
Structure Classification
- Phenols
- Polyphenols
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Publications (4)

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Journal Impact Factor

Vet Microbiol

Curcumin inhibits classical swine fever virus replication by interfering with lipid metabolism. [Abstract]

2021 Aug;259:109152. PMID: 34146894
Future Pharmacol

2024 Mar 8, 4(1), 256-278.
Research Square Preprint

2024 Oct 04.
Heliyon

Combined bisdemethoxycurcumin and potassium iodide-mediated antimicrobial photodynamic therapy. [Abstract]

2023 Jun 27;9(7):e17490. PMID: 37455953

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : ≥ 100 mg/mL (324.33 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

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

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (8.11 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (272 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
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- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Lee PJ, et al. Bisdemethoxycurcumin Induces Apoptosis in Activated Hepatic Stellate Cells via Cannabinoid Receptor 2. Molecules. 2015 Jan 14;20(1):1277-92. [Content Brief]

[2]. Chen J, et al. Natural borneol enhances bisdemethoxycurcumin-induced cell cycle arrest in the G2/M phase through up-regulation of intracellular ROS in HepG2 cells. Food Funct. 2014 Dec 24. [Content Brief]

[3]. Luo C, et al. Bisdemethoxycurcumin attenuates gastric adenocarcinoma growth by inducing mitochondrial dysfunction. Oncol Lett. 2015 Jan;9(1):270-274. [Content Brief]

[4]. Li YB, et al. Bisdemethoxycurcumin Increases Sirt1 to Antagonize t-BHP-Induced Premature Senescence in WI38 Fibroblast Cells. Evid Based Complement Alternat Med. 2013;2013:851714. [Content Brief]

[5]. Yodkeeree S, et al. Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA. J Nutr Biochem. 2009 Feb;20(2):87-95. [Content Brief]

[6]. Lai CS, et al. Bisdemethoxycurcumin Inhibits Adipogenesis in 3T3-L1 Preadipocytes and Suppresses Obesity in High-Fat Diet-Fed C57BL/6 Mice. J Agric Food Chem. 2016 Feb 3;64(4):821-30. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.2433 mL	16.2164 mL	32.4328 mL	81.0820 mL
	5 mM	0.6487 mL	3.2433 mL	6.4866 mL	16.2164 mL
	10 mM	0.3243 mL	1.6216 mL	3.2433 mL	8.1082 mL
	15 mM	0.2162 mL	1.0811 mL	2.1622 mL	5.4055 mL
	20 mM	0.1622 mL	0.8108 mL	1.6216 mL	4.0541 mL
	25 mM	0.1297 mL	0.6487 mL	1.2973 mL	3.2433 mL
	30 mM	0.1081 mL	0.5405 mL	1.0811 mL	2.7027 mL
	40 mM	0.0811 mL	0.4054 mL	0.8108 mL	2.0270 mL
	50 mM	0.0649 mL	0.3243 mL	0.6487 mL	1.6216 mL
	60 mM	0.0541 mL	0.2703 mL	0.5405 mL	1.3514 mL
	80 mM	0.0405 mL	0.2027 mL	0.4054 mL	1.0135 mL
	100 mM	0.0324 mL	0.1622 mL	0.3243 mL	0.8108 mL

Keywords

(E,E)-Bisdemethoxycurcumin

4 Cited Publications

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(E,E)-Bisdemethoxycurcumin

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Publications Citing Use of MedChemExpress (MCE) (E,E)-Bisdemethoxycurcumin

Biologische Aktivität

Chemical Information

Publications (4)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

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Complete Stock Solution Preparation Table

(E,E)-Bisdemethoxycurcumin

Apoptosis Compound Library

Immunology/Inflammation Compound Library

Natural Product Library

Anti-Cancer Compound Library

Autophagy Compound Library

Medicine Food Homology Compound Library

Phenols Library

Traditional Chinese Medicine Active Compound Library

Anti-Cancer Natural Product Library

Anti-inflammatory Traditional Chinese Medicine Active Compound Library

Plant-Sourced Natural Product Library

Cell Death Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Natural Product Library Plus

Natural Product and Natural Product-Like Compound Library

Bioactive Compound Library

Miao Ethnicity Medicine Compound Library

PBCRBS Traditional Chinese Medicine Compound Library

Non-Alcoholic Fatty Liver Disease (NAFLD) Compound Library

RO5 Drug-like Natural Product Library

High-Throughput Bioactive Compound Library

High-Throughput Natural Product Library

Diarrhea-Related Traditional Chinese Medicine Active Compound Library

Mongolian Medicine Compound Library

Mass Spectrometry Natural Product Library

Publications Citing Use of MedChemExpress (MCE) (E,E)-Bisdemethoxycurcumin

Biologische Aktivität

Chemical Information

Publications (4)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

(E,E)-Bisdemethoxycurcumin Related Classifications

HY-N0007 Related Classifications