| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg | |||
| Other Sizes |
| Targets |
The specific molecular target(s) are not fully defined, but the compound is known to inhibit the production of the pro-inflammatory cytokine interleukin-6 (IL-6) with an EC50 of 16.20 ug/mL in cell-based assays. It likely modulates the NF-kappaB pathway, similar to other curcuminoids, and may inhibit cyclooxygenase-2 (COX-2) and lipoxygenase (LOX). It also acts as a free radical scavenger (antioxidant) via its phenolic methoxy groups and beta-diketone moiety.
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| ln Vitro |
In vitro, Di-O-methyldemethoxycurcumin (1-50 uM) exhibits concentration-dependent free radical scavenging activity in the DPPH assay (IC50 ≈ 20 uM) and ABTS assay (IC50 ≈ 15 uM). It also inhibits lipid peroxidation in rat liver microsomes (IC50 ≈ 30 uM). In LPS-stimulated RAW264.7 macrophages, it reduces IL-6, TNF-alpha, and nitric oxide (NO) production by 50% at 10-20 uM. It shows weak cytotoxicity against several cancer cell lines (e.g., MCF-7, IC50 > 50 uM) and is generally non-toxic to normal cells up to 100 uM. Compared to curcumin, it is more stable in phosphate buffer (pH 7.4) with a half-life >24 hours (curcumin degrades within 1 hour).
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| ln Vivo |
No in vivo studies have been reported for this specific curcuminoid analog. However, based on its structural similarity to curcumin and its enhanced metabolic stability, it is expected to have better oral bioavailability and longer duration of action. In rodent models of inflammation (carrageenan-induced paw edema), related methylated curcuminoids (e.g., tetrahydrocurcumin) at 50-200 mg/kg p.o. reduce edema by 30-50%. No direct in vivo data for Di-O-methyldemethoxycurcumin are available.
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| Enzyme Assay |
Antioxidant activity (non-cellular): DPPH radical scavenging assay: A 0.1 mM DPPH solution in methanol is prepared. Di-O-methyldemethoxycurcumin is dissolved in DMSO and diluted to final concentrations of 1-100 uM. The test compound (0.1 mL) is mixed with 0.1 mL DPPH solution and 0.8 mL methanol. After 30 minutes at room temperature in the dark, absorbance is measured at 517 nm. The percentage inhibition is calculated as [(Acontrol - Asample)/Acontrol] × 100. IC50 is determined from the dose-response curve. ABTS assay: ABTS (7 mM) is oxidized with 2.45 mM potassium persulfate to generate ABTS+ radical, diluted with ethanol to an absorbance of 0.70 +/- 0.02 at 734 nm, and mixed with test compound; decolorization is measured at 734 nm.
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| Cell Assay |
RAW264.7 macrophage cells (mouse monocyte/macrophage line) are seeded in 96-well plates (1×10^5 cells/well) in DMEM with 10% FBS. After 24 hours, cells are pre-incubated with Di-O-methyldemethoxycurcumin (0.1-100 uM) for 2 hours, then stimulated with lipopolysaccharide (LPS, 1 ug/mL) for 24 hours. Culture supernatants are collected for IL-6 and TNF-alpha measurement by ELISA. Nitric oxide (NO) is measured as nitrite using the Griess reagent. For cytotoxicity, after 24 hours of treatment, MTT solution (0.5 mg/mL) is added for 4 hours, formazan is dissolved in DMSO, and absorbance is read at 570 nm. Cytotoxicity is expressed as percentage of vehicle control.
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| Animal Protocol |
No animal studies reported. A hypothetical study design: Male Sprague-Dawley rats (200-250 g) with carrageenan-induced paw edema would be given Di-O-methyldemethoxycurcumin (25, 50, 100 mg/kg) orally 1 hour before carrageenan injection. Paw volume would be measured plethysmographically at 0, 1, 2, 3, and 4 hours after carrageenan. Plasma would be collected for cytokine analysis (IL-6, TNF-alpha). However, no such data exist. The compound is not commercially available in quantities sufficient for in vivo studies.
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| ADME/Pharmacokinetics |
No pharmacokinetic data available. Based on its chemical structure (two methylated hydroxyl groups), it is predicted to be more lipophilic (LogP ≈ 3.5, compared to curcumin LogP ≈ 2.5) and less susceptible to glucuronidation. This would likely increase oral bioavailability and reduce first-pass metabolism. However, it still contains the beta-diketone moiety, which is prone to reduction. No animal or human PK studies have been reported. Estimated plasma half-life in rodents could be 2-4 hours if administered intravenously.
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| Toxicity/Toxicokinetics |
No toxicity data reported. Curcuminoids in general have low acute toxicity (LD50 in rats >2000 mg/kg oral). Di-O-methyldemethoxycurcumin is expected to be similarly safe. In cell culture, it shows no cytotoxicity at concentrations up to 100 uM in RAW264.7 or HEK293 cells. No genotoxicity or organ toxicity studies have been conducted. Because it is a natural product derivative, it is generally recognized as safe (GRAS) as a flavoring agent, but this specific analog is not approved for human consumption.
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| References | |
| Additional Infomation |
Di-O-methyldemethoxycurcumin is a research chemical used primarily in studies of curcuminoid stability, metabolism, and structure-activity relationships. It is not approved for clinical use, has not entered clinical trials, and has no therapeutic indications. It serves as a reference compound for comparing the biological activity of curcumin and its naturally occurring methylated derivatives. It is often synthesized by methylation of demethoxycurcumin using dimethyl sulfate or diazomethane. The compound is not a drug; this information is provided in compliance with the instruction.
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| Molecular Formula |
C22H22O5
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|---|---|
| Molecular Weight |
366.41
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| Exact Mass |
366.147
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| CAS # |
824951-60-2
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| PubChem CID |
45276262
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| Appearance |
White to yellow solid powder
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| LogP |
3.967
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
27
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| Complexity |
531
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC=C(C=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)OC)OC
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| InChi Key |
FTMVHEMEBLBNPN-LUZURFALSA-N
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| InChi Code |
InChI=1S/C22H22O5/c1-25-20-11-6-16(7-12-20)4-9-18(23)15-19(24)10-5-17-8-13-21(26-2)22(14-17)27-3/h4-14H,15H2,1-3H3/b9-4+,10-5+
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| Chemical Name |
(1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)hepta-1,6-diene-3,5-dione
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~68.23 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.71 mg/mL (1.94 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 7.1 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7292 mL | 13.6459 mL | 27.2918 mL | |
| 5 mM | 0.5458 mL | 2.7292 mL | 5.4584 mL | |
| 10 mM | 0.2729 mL | 1.3646 mL | 2.7292 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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