demethoxycurcumin
demethoxycurcumin structure
|
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 | Chinese USA | Flash Point | 205.5±23.6 °C | |
| Symbol |
GHS09 |
Signal Word | Warning | |
Use of demethoxycurcuminDemethoxycurcumin(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. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | demethoxycurcumin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| 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 |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| 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 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
|
~%
demethoxycurcumin CAS#:22608-11-3 |
| Literature: US2010/48957 A1, ; Page/Page column 4-5 ; |
|
~52%
demethoxycurcumin CAS#:22608-11-3 |
| Literature: Venkateswarlu, Somepalli; Ramachandra, Marellapudi S.; Subbaraju, Gottumukkala V. Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 23 p. 6374 - 6380 |
|
~%
Detail
Learn More
|
| Literature: Journal of Natural Products, , vol. 61, # 12 p. 1531 - 1534 |
|
~%
Detail
Learn More
|
| Literature: Journal of Natural Products, , vol. 61, # 12 p. 1531 - 1534 |
|
~%
Detail
Learn More
|
| Literature: Journal of Natural Products, , vol. 61, # 12 p. 1531 - 1534 |
|
~%
demethoxycurcumin CAS#:22608-11-3 |
| Literature: Molecules, , vol. 16, # 2 p. 1888 - 1900 |
|
~%
demethoxycurcumin CAS#:22608-11-3 |
| Literature: Molecules, , vol. 16, # 2 p. 1888 - 1900 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 3 | |
|---|---|
| DownStream 2 | |
CAS#:1135-24-6
CAS#:7400-08-0This table lists relevant public references with title, journal and publication metadata for this compound.
|
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... |
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| (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 |
| Demethoxy Curcumin |
| demethoxycurcumin |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What are the storage conditions for demethoxycurcumin? |
| A: Storage conditions for demethoxycurcumin: 2-8°C. |
| Q: What is the SMILES notation of demethoxycurcumin? |
| A: SMILES notation of demethoxycurcumin is COc1cc(C=CC(=O)CC(=O)C=Cc2ccc(O)cc2)ccc1O. |
| Q: What is the safety information for demethoxycurcumin? |
| A: Safety information for demethoxycurcumin: 61. |
| Q: What is the melting point of demethoxycurcumin? |
| A: Melting point of demethoxycurcumin is 168ºC. |
| Q: What are the downstream products of demethoxycurcumin? |
| A: Related downstream products(CAS) of demethoxycurcumin: 1135-24-6;7400-08-0. |
| Q: What English synonyms does demethoxycurcumin have? |
| A: English synonyms of demethoxycurcumin: (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, Demethoxy Curcumin, demethoxycurcumin. |
| Q: What is the polar surface area (PSA) of demethoxycurcumin? |
| A: Polar surface area (PSA) of demethoxycurcumin is 83.83000. |
| Q: What are the upstream materials of demethoxycurcumin? |
| A: Related upstream materials(CAS) of demethoxycurcumin: 123-08-0;121-33-5;123-54-6. |
| Q: What is the LogP of demethoxycurcumin? |
| A: LogP of demethoxycurcumin is 3.15. |
| Q: What is the physical appearance of demethoxycurcumin? |
| A: demethoxycurcumin appears as orange. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| naturewill |