-3,4,5-Trimethoxycinnamic acid Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C12H14O5 |
| Molecular Weight | 238.2366 |
| Exact Mass | 238.084 |
| CAS # | 20329-98-0 |
| PubChem CID | 735755 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 396.4±37.0 °C at 760 mmHg |
| Melting Point | 125-127ºC(lit.) |
| Flash Point | 151.5±20.0 °C |
| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
| Index of Refraction | 1.560 |
| LogP | 2 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 17 |
| Complexity | 262 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)O |
| InChi Key | YTFVRYKNXDADBI-SNAWJCMRSA-N |
| InChi Code | InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+ |
| Chemical Name | (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid |
| 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 | In cerebellar granule cells, (E)-3,4,5-Trimethoxycinnamic Acid (10 μg/mL, 1 h) enhances the expression of GAD65 and GABAA receptor γ subunit [3]. Cl-influx significantly increased in response to (E)-3,4,5-Trimethoxycinnamic acid (0–10 μg/mL, 1 h) [3]. |
| ln Vivo | (E)-3,4,5-Trimethoxycinnamic acid (0–20 mg/kg IP once) exhibits antiepileptic properties [2]. (E)-3,4,5-Trimethoxycinnamic Acid (0–10 mg/kg, orally administered once) can increase the hypnotizing effect in mice administered pentobarbital [3]. |
| Cell Assay |
Western Blot analysis [3] Cell Types: primary cultured cerebellar granule cells Tested Concentrations: 10 μg/mL Incubation Duration: 1 h Experimental Results: The expression of GAD65 (glutamic acid decarboxylase) and GABAA receptor γ subunit increased, but not Affects the content of a and b subunits in GABAA receptors. Cell viability assay [3] Cell Types: Primary cultured cerebellar granule cells Tested Concentrations: 1, 3, 5, 10 μg/mL Incubation Duration: 1 hour Experimental Results: Cl- influx increased Dramatically. |
| Animal Protocol |
Animal/Disease Models: Adult male Kunming mice (18-20 g, maximum electroshock (MES) and pentylenetetrazole (PTZ) models) [2] Doses: 5, 10 and 20 mg/kg; 10 mL/kg Route of Administration: IP, primary Experimental Results: The incidence of MES-induced THE (tetanic hindlimb extension) was Dramatically diminished to 50% and 20% of vehicle control values at 10 and 20 mg/kg. At the 5 mg/kg dose, the incidence of MES-induced THE was only diminished by 80%. In a PTZ seizure model, the onset of myoclonic jerks (MJ) was Dramatically delayed and seizure severity and mortality were diminished compared with vehicle-treated animals. The incidence of generalized clonic convulsions (stage 4) disappeared at both 10 and 20 mg/kg doses. Animal/Disease Models: ICR male mice (25-28 g, 10-12 per group) [3] Doses: 2, 5 and 10 mg/kg Route of Administration: oral (po), once, 15 minutes and 1 before injection hour, results of pentobarbital injection: significant decrease in locomotor activity at 10 mg/kg. NREM and total sleep time increased, but wakefulness decreas |
| References |
[1]. Research progress in the biological activities of 3,4,5-trimethoxycinnamic acid (TMCA) derivatives. Eur J Med Chem. 2019 Jul 1;173:213-227. [2]. 3,4,5-Trimethoxycinnamic acid, one of the constituents of Polygalae Radix exerts anti-seizure effects by modulating GABAAergic systems in mice. J Pharmacol Sci. 2016 May;131(1):1-5. [3]. 3,4,5-Trimethoxycinnamic acid (TMCA), one of the constituents of Polygalae Radix enhances pentobarbital-induced sleeping behaviors via GABAAergic systems in mice. Arch Pharm Res. 2013 Oct;36(10):1244-51. |
| Additional Infomation |
3,4,5-trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate. 3,4,5-Trimethoxycinnamic acid has been reported in Polygala tenuifolia, Piper swartzianum, and Piper tuberculatum with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~419.74 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.49 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 (10.49 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (10.49 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1974 mL | 20.9872 mL | 41.9745 mL | |
| 5 mM | 0.8395 mL | 4.1974 mL | 8.3949 mL | |
| 10 mM | 0.4197 mL | 2.0987 mL | 4.1974 mL |