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22608-11-3

22608-11-3 structure
22608-11-3 structure
  • Name: demethoxycurcumin
  • Chemical Name: demethoxycurcumin
  • CAS Number: 22608-11-3
  • Molecular Formula: C20H18O5
  • Molecular Weight: 338.354
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-02-17 08:00:00
  • Modify Date: 2024-01-02 19:36:55
  • 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.

Name demethoxycurcumin
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
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
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.

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 orange
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.660
Storage condition 2-8°C
Water Solubility DMSO: ≥10mg/mL
Symbol GHS09
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