CAS 22608-11-3|demethoxycurcumin

Introduction：Basic information about CAS 22608-11-3|demethoxycurcumin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. demethoxycurcumin BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles29
6. Synonyms

Common Name	demethoxycurcumin
CAS Number	22608-11-3	Molecular Weight	338.354
Density	1.3±0.1 g/cm3	Boiling Point	571.4±50.0 °C at 760 mmHg
Molecular Formula	C₂₀H₁₈O₅	Melting Point	168ºC
MSDS	ChineseUSA	Flash Point	205.5±23.6 °C
Symbol	GHS09	Signal Word	Warning

Names

Name	demethoxycurcumin
Synonym	More Synonyms

demethoxycurcumin BiologicalActivity

Description	Demethoxycurcumin(Curcumin II) is a major active curcuminoid; possess anti-inflammatory properties; also exert cytotoxic effects in human cancer cells via induction of apoptosis.IC50 value: Target:in vitro: DMC significantly decreased NO secretion by 35-41% in our inflamed cell model. Decrease in NO production by DMC was concomitant with down-regulation of iNOS at mRNA and protein levels compared to proinflammatory cytokine cocktail and LPS-treated controls. Mechanism of action of DMC may be partly due to its potent inhibition of the iNOS pathway [1]. BDMCCN has the strongest inhibitory activity toward BACE-1 with 17 μM IC50, which was 20 and 13 times lower than those of CCN and DMCCN respectively [2]. Genes associated with DNA damage and repair, cell-cycle check point and apoptosis could be altered by DMC; in particular, 144 genes were found up-regulated and 179 genes down-regulated in NCI-H460 cells after exposure to DMC [3]. in vivo: At low doses, both the curcuminoid mixture and curcumin I did not affect brain stimulation reward, whereas, higher doses increased ICSS thresholds. Curcumin II and curcumin III did not affect brain stimulation reward at any doses. Subthreshold doses of the curcuminoid mixture and curcumin I inhibited the reward-facilitating effect of morphine.
Related Catalog	Signaling Pathways >>Apoptosis >>ApoptosisSignaling Pathways >>Autophagy >>AutophagyNatural Products >>PhenolsResearch Areas >>Inflammation/Immunology
References	[1]. Somchit M, et al. Demethoxycurcumin from Curcuma longa rhizome suppresses iNOS induction in an in vitro inflamed human intestinal mucosa model. Asian Pac J Cancer Prev. 2014;15(4):1807-10. [2]. Wang X, et al. Effects of curcuminoids identified in rhizomes of Curcuma longa on BACE-1 inhibitory and behavioral activity and lifespan of Alzheimer's disease Drosophila models. BMC Complement Altern Med. 2014 Mar 5;14:88. [3]. Ko YC, et al. Demethoxycurcumin Alters Gene Expression Associated with DNA Damage, Cell Cycle and Apoptosis in Human Lung Cancer NCI-H460 Cells In Vitro. In Vivo. 2015 01-02;29(1):83-94. [4]. Katsidoni V, et al. Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit morphine's rewarding effect in rats. Psychopharmacology (Berl). 2014 Dec;231(23):4467-78.

Description

Demethoxycurcumin(Curcumin II) is a major active curcuminoid; possess anti-inflammatory properties; also exert cytotoxic effects in human cancer cells via induction of apoptosis.IC50 value: Target:in vitro: DMC significantly decreased NO secretion by 35-41% in our inflamed cell model. Decrease in NO production by DMC was concomitant with down-regulation of iNOS at mRNA and protein levels compared to proinflammatory cytokine cocktail and LPS-treated controls. Mechanism of action of DMC may be partly due to its potent inhibition of the iNOS pathway [1]. BDMCCN has the strongest inhibitory activity toward BACE-1 with 17 μM IC50, which was 20 and 13 times lower than those of CCN and DMCCN respectively [2]. Genes associated with DNA damage and repair, cell-cycle check point and apoptosis could be altered by DMC; in particular, 144 genes were found up-regulated and 179 genes down-regulated in NCI-H460 cells after exposure to DMC [3]. in vivo: At low doses, both the curcuminoid mixture and curcumin I did not affect brain stimulation reward, whereas, higher doses increased ICSS thresholds. Curcumin II and curcumin III did not affect brain stimulation reward at any doses. Subthreshold doses of the curcuminoid mixture and curcumin I inhibited the reward-facilitating effect of morphine.

Related Catalog

Signaling Pathways >>Apoptosis >>ApoptosisSignaling Pathways >>Autophagy >>AutophagyNatural Products >>PhenolsResearch Areas >>Inflammation/Immunology

References

[1]. Somchit M, et al. Demethoxycurcumin from Curcuma longa rhizome suppresses iNOS induction in an in vitro inflamed human intestinal mucosa model. Asian Pac J Cancer Prev. 2014;15(4):1807-10.

[2]. Wang X, et al. Effects of curcuminoids identified in rhizomes of Curcuma longa on BACE-1 inhibitory and behavioral activity and lifespan of Alzheimer's disease Drosophila models. BMC Complement Altern Med. 2014 Mar 5;14:88.

[3]. Ko YC, et al. Demethoxycurcumin Alters Gene Expression Associated with DNA Damage, Cell Cycle and Apoptosis in Human Lung Cancer NCI-H460 Cells In Vitro. In Vivo. 2015 01-02;29(1):83-94.

[4]. Katsidoni V, et al. Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit morphine's rewarding effect in rats. Psychopharmacology (Berl). 2014 Dec;231(23):4467-78.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	571.4±50.0 °C at 760 mmHg
Melting Point	168ºC
Molecular Formula	C₂₀H₁₈O₅
Molecular Weight	338.354
Flash Point	205.5±23.6 °C
Exact Mass	338.115417
PSA	83.83000
LogP	3.15
Appearance of Characters	orange
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.660
InChIKey	HJTVQHVGMGKONQ-LUZURFALSA-N
SMILES	COc1cc(C=CC(=O)CC(=O)C=Cc2ccc(O)cc2)ccc1O
Storage condition	2-8°C
Water Solubility	DMSO: ≥10mg/mL

Safety Information

Symbol	GHS09
Signal Word	Warning
Hazard Statements	H400
Precautionary Statements	P273
Hazard Codes	N
Risk Phrases	50
Safety Phrases	61
RIDADR	UN 3077 9 / PGIII
HS Code	29145090

Articles29

Therapeutic potential of turmeric in Alzheimer's disease: curcumin or curcuminoids?

Phytother Res. 28(4) , 517-25, (2014)

Alzheimer's disease (AD) is the most common form of dementia. There is limited choice in modern therapeutics, and drugs available have limited success with multiple side effects in addition to high co...

Differential cellular uptake and metabolism of curcuminoids in monocytes/macrophages: regulatory effects on lipid accumulation.

Br. J. Nutr. 112(1) , 8-14, (2014)

We have previously shown that curcumin (CUR) may increase lipid accumulation in cultured human acute monocytic leukaemia cell line THP-1 monocytes/macrophages, but that tetrahydrocurcumin (THC), an in...

Demethoxycurcumin-induced DNA Damage Decreases DNA Repair-associated Protein Expression Levels in NCI-H460 Human Lung Cancer Cells.

Anticancer Res. 35 , 2691-8, (2015)

Demethoxycurcumin (DMC) is a key component of Chinese medicine (Turmeric) and has been proven effective in killing various cancer cells. Its role in inducing cytotoxic effects in many cancer cells has...

Synonyms

(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione

(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione

1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-

Demethoxy Curcumin

1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-, (1E,6E)-

demethoxycurcumin

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