5,7,4'-Trimethoxyflavone is a naturally occuring flavnoid extracted from Kaempferia parviflora (KP) that is a famous medicinal plant from Thailand. Increases in the sub-G1 phase, DNA fragmentation, annexin-V/PI staining, the Bax/Bcl-xL ratio, proteolytic activation of caspase-3, and the degradation of poly (ADP-ribose) polymerase (PARP) protein are all signs that 5,7,4'-trimethoxyflavone causes apoptosis. In a concentration-dependent manner, 5,7,4'-trimethoxyflavone significantly inhibits the growth of SNU-16 human gastric cancer cells.
Physicochemical Properties
| Molecular Formula | C18H16O5 |
| Molecular Weight | 312.3166 |
| Exact Mass | 312.1 |
| CAS # | 5631-70-9 |
| Related CAS # | 5631-70-9 |
| PubChem CID | 79730 |
| Appearance | Light yellow to yellow solid |
| Density | 1.242g/cm3 |
| Boiling Point | 506.5ºC at 760mmHg |
| Melting Point | 158-160ºC (dec.) |
| Flash Point | 225.5ºC |
| Index of Refraction | 1.585 |
| LogP | 3.485 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 23 |
| Complexity | 452 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O1C(=C([H])C(C2C(=C([H])C(=C([H])C1=2)OC([H])([H])[H])OC([H])([H])[H])=O)C1C([H])=C([H])C(=C([H])C=1[H])OC([H])([H])[H] |
| InChi Key | ZXJJBDHPUHUUHD-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3 |
| Chemical Name | 5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one |
| Synonyms | 5,7,4'-Trimethoxyflavone |
| 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
| Targets | Caspase-3; PARP |
| ln Vitro | In vitro, 5,7,4'-Trimethoxyflavone (12.5, 25, 50, 100, 200 μM, 24, 48 h) suppresses SUN-16 cell division [1]. 11, 25, 5,7,4'-Trimethoxyflavone endoplasmic reticulum and associated regulatory proteins to 5,7,4'-trimethoxyflavone (6.25, 12.5 μM, 24 h) in SUN-16 cells yields cytostatic effects[1]. The activity of ROS and pro-inflammatory regulatory factors caused by TNF-α in HDFs cells can be inhibited by 5,7,4'-Trimethoxyflavone (6.25, 12.5 μM, 24 h). |
| Cell Assay |
Cell Viability Assay[1] Cell Types: AGS, SNU-1, SNU-16 Tested Concentrations: 12.5 ,25, 50, 100, 200 μM Incubation Duration: 24 and 48 hrs (hours) Experimental Results: demonstrated the highest results in SNU-16 cells toxicity. Apoptosis analysis [1] Cell Types: SNU-16 Tested Concentrations: 12.5, 25, 37.5, 50 μM Incubation Duration: 24 h Experimental Results: The percentage of annexin V-positive SNU-16 cells increased from 7.2% to 58.0%, and GRP78, IRE1a , ATF-4 and CHOP. Western Blot Analysis[2] Cell Types: HDF Tested Concentrations: 6.25, 12.5 μM Incubation Duration: 24 hrs (hours) Experimental Results: Inhibits matrix metalloproteinase-1 (MMP-1) expression and stimulates collagen, type I and alpha 1 (COLIA1) expression. |
| References |
[1]. Induction of ER Stress-Mediated Apoptosis by the Major Component 5,7,4'-TrimethoxyflavoneIsolated from Kaempferia parviflora Tea Infusion. Nutr Cancer. 2018 Aug-Sep;70(6):984-996. [2]. Protective Effect of Polymethoxyflavones Isolated from Kaempferia parviflora against TNF-α-Induced Human Dermal Fibroblast Damage. Antioxidants (Basel). 2021 Oct 13;10(10):1609. [3]. Activation of the CFTR Cl- channel by trimethoxyflavone in vitro and in vivo. Cell Physiol Biochem. 2008;22(5-6):685-92. |
| Additional Infomation |
4',5,7-Trimethoxyflavone is an ether and a member of flavonoids. 4',5,7-Trimethoxyflavone has been reported in Boesenbergia rotunda, Citrus myrtifolia, and other organisms with data available. See also: Tangerine peel (part of). |
Solubility Data
| Solubility (In Vitro) |
DMSO: 62~100 mg/mL (198.5~320.2 mM) Ethanol: ~15 mg/mL (~48.0 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2018 mL | 16.0092 mL | 32.0184 mL | |
| 5 mM | 0.6404 mL | 3.2018 mL | 6.4037 mL | |
| 10 mM | 0.3202 mL | 1.6009 mL | 3.2018 mL |