-Demethoxycurcumin Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C20H18O5 |
| Molecular Weight | 338.35392 |
| Exact Mass | 338.115 |
| CAS # | 24939-17-1 |
| Related CAS # | Demethoxycurcumin;22608-11-3 |
| PubChem CID | 5469424 |
| Appearance | Yellow to orange solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 571.4±50.0 °C at 760 mmHg |
| Melting Point | 168 °C |
| Flash Point | 205.5±23.6 °C |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
| Index of Refraction | 1.660 |
| LogP | 3.15 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 25 |
| Complexity | 502 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O |
| InChi Key | HJTVQHVGMGKONQ-LUZURFALSA-N |
| InChi Code | InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+ |
| Chemical Name | (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
(E/Z)-Demethoxycurcumin exhibited concentration-dependent anticoagulant activity in vitro. In human plasma, it prolonged the prothrombin time (PT) and activated partial thromboplastin time (APTT). At a concentration of 100 μg/mL, PT was extended by 32% and APTT by 41% compared to the control group. At 200 μg/mL, PT and APTT were prolonged by 58% and 65% respectively, showing significant dose-related anticoagulative effects [1] The compound inhibited thrombin-induced fibrin formation. In a fibrin clotting assay, (E/Z)-Demethoxycurcumin (50-200 μg/mL) suppressed fibrin clot formation in a concentration-dependent manner, with 50% inhibition at 125 μg/mL [1] |
| Enzyme Assay |
Prothrombin time (PT) assay: Human plasma was mixed with (E/Z)-Demethoxycurcumin (25-200 μg/mL) and incubated at 37°C for 3 minutes. Thromboplastin-calcium reagent was added, and the time required for clot formation was recorded using a coagulometer. The assay was repeated three times, and the mean PT values were calculated to assess extrinsic pathway inhibition [1] Activated partial thromboplastin time (APTT) assay: Human plasma was incubated with (E/Z)-Demethoxycurcumin (25-200 μg/mL) and APTT reagent at 37°C for 5 minutes. Calcium chloride solution was added, and the clotting time was measured. This assay evaluated the inhibition of the intrinsic coagulation pathway [1] Thrombin-induced fibrin clotting assay: Fibrinogen solution was mixed with (E/Z)-Demethoxycurcumin (50-200 μg/mL) and thrombin. The mixture was incubated at 37°C, and the time to form a visible fibrin clot was recorded. Inhibition rate was calculated by comparing with the clotting time of the vehicle control [1] |
| ADME/Pharmacokinetics |
Metabolism / Metabolites Demethoxycurcumin has known human metabolites that include Demethoxycurcumin O-glucuronide. |
| References |
[1]. Studies on active substances in the herbs used for Oketsu (“stagnant blood”) in Chinese medicine. III. On the anticoagulative principles in curcumae rhizoma. CHEMICAL & PHARMACEUTICAL BULLETIN, 1985;33(4):1499–1502. |
| Additional Infomation |
Demethoxycurcumin is a beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior. It has a role as a metabolite, an antineoplastic agent and an anti-inflammatory agent. It is a polyphenol, a beta-diketone, an enone and a diarylheptanoid. Demethoxycurcumin has been reported in Curcuma xanthorrhiza, Curcuma kwangsiensis, and other organisms with data available. (E/Z)-Demethoxycurcumin is a natural active component isolated from Curcumae Rhizoma (turmeric rhizome), a Chinese medicinal herb used for treating "stagnant blood" (Oketsu) [1] It is identified as one of the key anticoagulative principles in Curcumae Rhizoma, exerting its activity by targeting the coagulation cascade (both intrinsic and extrinsic pathways) and inhibiting thrombin-mediated fibrin formation [1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9555 mL | 14.7776 mL | 29.5552 mL | |
| 5 mM | 0.5911 mL | 2.9555 mL | 5.9110 mL | |
| 10 mM | 0.2956 mL | 1.4778 mL | 2.9555 mL |