Art. -Nr.: HY-N0007A

Bisdemethoxycucurmin

(Synonyms: Curcumin III; Didemethoxycurcumin)

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Bisdemethoxycucurmin (Curcumin III) is a curcuminoid compound and an inhibitor of P-glycoprotein and ferroptosis. Bisdemethoxycucurmin exhibits multiple activities such as anti-oxidation, anti-inflammation and anti-tumor. Bisdemethoxycucurmin can be used for the research of tumors and inflammatory diseases.

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Reinheit: 98.77%
CAS. Nr.: 24939-16-0
Formel: C₁₉H₁₆O₄
Molecular Weight:308.33

Speicherung:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Bisdemethoxycucurmin Chemical Structure

CAS. Nr.: 24939-16-0

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

Biologische Aktivität

Beschreibung

Alle DNA/RNA Synthesis Isoform-spezifische Produkte anzeigen :

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]
Caco-2	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of differentiated human Caco2 cells measured after 72 hrs by SRB assay Growth inhibition of differentiated human Caco2 cells measured after 72 hrs by SRB assay	[PMID: 27521589]
Caco-2	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of undifferentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay Growth inhibition of undifferentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay	[PMID: 27521589]
Caco-2	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of undifferentiated human Caco2 cells measured after 72 hrs by SRB assay Growth inhibition of undifferentiated human Caco2 cells measured after 72 hrs by SRB 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	>25 μM Compound: 1b; BDMC	Growth inhibition of CHOK1 cells measured after 72 hrs by SRB assay Growth inhibition of CHOK1 cells measured after 72 hrs by SRB 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	>25 μM Compound: 1b; BDMC	Growth inhibition of human EAhy926 cells measured after 72 hrs by SRB assay Growth inhibition of human EAhy926 cells measured after 72 hrs by SRB 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]
HT-29	IC₅₀	>25 μM Compound: 1b; BDMC	Growth inhibition of human HT-29 cells measured after 72 hrs by SRB assay Growth inhibition of human HT-29 cells measured after 72 hrs by SRB 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

Bisdemethoxycucurmin (24 h) inhibits lipid peroxidation in primary rat nucleus pulposus cells treated with TNF-α^[1].
Bisdemethoxycucurmin (1-10 μg/mL; 4 h) is cytotoxic and inhibits DNA synthesis in human chronic myeloid leukemia cells^[2].

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

In Vivo

Bisdemethoxycucurmin (72.5 μg; topical application; 7 times) exhibits antitumor activity in a mouse skin papilloma model^[2].

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

Animal Model:

Swiss bald (hairless) female mice treated DMBA (HY-W011845)^[2]
Dosage:

72.5 μg
Administration:

Topical application; 7 times: applied 3 days before and twice weekly for 3 weeks after DMBA (HY-W011845) treatment
Result:

Significantly reduced the incidence of skin papillomas from 100% in the DMBA-only group to 75%.
Decreased the mean number of papillomas per mouse from 6.5 to 2.8.

Chemical Information

CAS. Nr. 24939-16-0
Appearance Solid
Molecular Weight 308.33
Formel C₁₉H₁₆O₄
Color Light 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

Curcumin III; Didemethoxycurcumin
Structure Classification
- Phenols
- Polyphenols
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 66.67 mg/mL (216.23 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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)}

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (269 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- 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]. Zhang P, et al. Cynarin alleviates intervertebral disc degeneration via protecting nucleus pulposus cells from ferroptosis. Biomed Pharmacother. 2023 Sep;165:115252. [Content Brief]

[2]. Nagabhushan, et al. Curcumin as an inhibitor of cancer. Journal of the American College of Nutrition 11.2. 1992. 192-198.

[3]. Chearwae W, et al. Biochemical mechanism of modulation of human P-glycoprotein (ABCB1) by curcumin I, II, and III purified from Turmeric powder. Biochem Pharmacol. 2004 Nov 15;68(10):2043-52. [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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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

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Bisdemethoxycucurmin

Ferroptosis Compound Library

Medicine Food Homology Compound Library

Phenols Library

Traditional Chinese Medicine Active Compound Library

Anti-Blood Cancer Compound Library

Food-Sourced Compound Library

Anti-Cancer Natural Product Library

Anti-inflammatory Traditional Chinese Medicine Active Compound Library

Plant-Sourced Natural Product Library

Human Metabolite Library

Cancer Stem Cells Compound Library

Cell Death Library

Anti-Hematopathy Compound Library

Anti-Ovarian Cancer Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Natural Product Library Plus

Bioactive Compound Library

PBCRBS Traditional Chinese Medicine Compound Library

RO5 Drug-like Natural Product Library

High-Throughput Bioactive Compound Library

High-Throughput Natural Product Library

Ancient Chinese Classical Formulas Traditional Chinese Medicine Active Compound Library

Mass Spectrometry Human Metabolite Library

Diarrhea-Related Traditional Chinese Medicine Active Compound Library

Mass Spectrometry Natural Product Library

Natural Product and Natural Product-Like Compound Library

Cell Cycle/DNA Damage Compound Library

Immunology/Inflammation Compound Library

Membrane Transporter/Ion Channel Compound Library

Natural Product Library

Anti-Cancer Compound Library

Anti-Aging Compound Library

Alle DNA/RNA Synthesis Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Bisdemethoxycucurmin Related Classifications

HY-N0007A Related Classifications