3,4,5-Trimethoxycinnamic acidCAS# 90-50-6 |
- 3,4,5-Trimethoxy-trans-cinnamic acid
Catalog No.:BCN3423
CAS No.:20329-98-0
Quality Control & MSDS
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| Cas No. | 90-50-6 | SDF | Download SDF |
| PubChem ID | 7021 | Appearance | White cryst. |
| Formula | C12H14O5 | M.Wt | 238.24 |
| Type of Compound | Phenylpropanoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid | ||
| SMILES | COC1=CC(=CC(=C1OC)OC)C=CC(=O)O | ||
| Standard InChIKey | YTFVRYKNXDADBI-UHFFFAOYSA-N | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 3,4,5-Trimethoxycinnamic acid has anti-stress effect, prolonging the sleeping time in animals. 3,4,5-Trimethoxycinnamic acid may exert anti-seizure activity by acting at the GABAA/BZ receptor complex. It shows hypoxia inducible factor-2 (HIF-2) inhibitory activity with EC50 value of 60.6 uM. 3,4,5-Trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5-HT(1A) receptor agonist in mice. |
| Targets | 5-HT Receptor | ERK | GABA Receptor | HIF-2 |
| In vivo | Synthesis and evaluation of a series of 3,4,5-trimethoxycinnamic acid derivatives as potential antinarcotic agents.[Pubmed: 23121934]Chem Biol Drug Des. 2013 Mar;81(3):389-98.A series of 3,4,5-Trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. Anti-stress effects of 3,4,5-trimethoxycinnamic acid, an active constituent of roots of Polygala tenuifolia (Onji).[Pubmed: 15305046]Biol Pharm Bull. 2004 Aug;27(8):1317-9.3,4,5-Trimethoxycinnamic acid (TMCA) is one of the constituents in Onji (roots of Polygala tenuifolia WILLD), an herbal medicine used for sedative in Japanese traditional Kampo medicine. Our previous study revealed that oral administration of this compound prolongs sleeping time induced by hexobarbital in mice to exhibit sedative action. |
| Kinase Assay | 3,4,5-Trimethoxycinnamic acid (TMCA), one of the constituents of Polygalae Radix enhances pentobarbital-induced sleeping behaviors via GABAAergic systems in mice.[Pubmed: 23852644]Arch Pharm Res. 2013 Oct;36(10):1244-51.These experiments were performed to investigate whether 3,4,5-Trimethoxycinnamic acid (TMCA), one of the constituents derived from Polygalae Radix, enhances pentobarbital-induced sleeping behaviors, and to alter sleep architecture through the γ-aminobutyric acid (GABA)ergic systems in mice. |
| Structure Identification | Chem Pharm Bull (Tokyo). 2011;59(9):1178-9.A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of Piper sarmentosum.[Pubmed: 21881266 ]
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3,4,5-Trimethoxycinnamic acid Dilution Calculator
3,4,5-Trimethoxycinnamic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.1974 mL | 20.9872 mL | 41.9745 mL | 83.949 mL | 104.9362 mL |
| 5 mM | 0.8395 mL | 4.1974 mL | 8.3949 mL | 16.7898 mL | 20.9872 mL |
| 10 mM | 0.4197 mL | 2.0987 mL | 4.1974 mL | 8.3949 mL | 10.4936 mL |
| 50 mM | 0.0839 mL | 0.4197 mL | 0.8395 mL | 1.679 mL | 2.0987 mL |
| 100 mM | 0.042 mL | 0.2099 mL | 0.4197 mL | 0.8395 mL | 1.0494 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of Piper sarmentosum.[Pubmed:21881266]
Chem Pharm Bull (Tokyo). 2011;59(9):1178-9.
A new trimethoxycinnamoyl-2-pyrrolinone alkaloid, langkamide (1), along with the known compounds piplartine (2) and 3,4,5-Trimethoxycinnamic acid (3) were isolated from the roots and stems of the shrub Piper sarmentosum ROXB. The structures were established by spectroscopic analyses and comparison of their spectral data with values reported in the literature. The compounds were tested for their ability to modulate hypoxia inducible factor-2 (HIF-2) transcription activity and all three showed HIF-2 inhibitory activity with EC(5)(0) values of 14.0, 4.8, and 60.6 muM, respectively, for compounds 1, 2, and 3.
Synthesis and evaluation of a series of 3,4,5-trimethoxycinnamic acid derivatives as potential antinarcotic agents.[Pubmed:23121934]
Chem Biol Drug Des. 2013 Mar;81(3):389-98.
A series of 3,4,5-Trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6-7, esters 9-12 through condensation reaction, and amides 13-19 via coupling reaction using 1-hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone-induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5-Trimethoxycinnamic acid derivatives (20 mg/kg/day). Most of 3,4,5-Trimethoxycinnamic acid derivatives were found to have high affinity to 5-HT(1A) receptor. The naloxone-induced morphine withdrawal syndrome was attenuated by (+)8-OH-DPAT (0.1 mg/kg/day, i.p.), a 5-HT(1A) receptor agonist. In cortical neuronal cells, (+)8-OH-DPAT (1 muM) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5-HT(1A) receptor-specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5-Trimethoxycinnamic acid derivatives and the derivatives-mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5-Trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5-HT(1A) receptor agonist in mice.
3,4,5-Trimethoxycinnamic acid (TMCA), one of the constituents of Polygalae Radix enhances pentobarbital-induced sleeping behaviors via GABAAergic systems in mice.[Pubmed:23852644]
Arch Pharm Res. 2013 Oct;36(10):1244-51.
These experiments were performed to investigate whether 3,4,5-Trimethoxycinnamic acid (TMCA), one of the constituents derived from Polygalae Radix, enhances pentobarbital-induced sleeping behaviors, and to alter sleep architecture through the gamma-aminobutyric acid (GABA)ergic systems in mice. TMCA decreased the locomotor activity. TMCA prolonged total sleep time, and reduced sleep latency induced by pentobarbital, similar to muscimol, a GABAA agonist. From the electrocencephalogram recording for 6 h after TMCA administration, the number of sleep/wake cycles were reduced by TMCA. TMCA also increased the total sleep time and non-rapid eye movement (NREM) sleep. In addition, TMCA increased Cl(-) influx in primary cultured cerebellar granule cells of mice. TMCA increased the activation of glutamic acid decarboxylase (GAD) and the expressions of gamma-subunit of GABAA receptors in the cerebellar granule cells. However, alpha- and beta-subunits proteins of GABAA receptors were not increased. Therefore, TMCA would increase pentobarbital induced-sleep and NREM sleep in mice. These results indicate that TMCA may enhance sleep and alter sleep architecture through GABAAergic systyems.
Anti-stress effects of 3,4,5-trimethoxycinnamic acid, an active constituent of roots of Polygala tenuifolia (Onji).[Pubmed:15305046]
Biol Pharm Bull. 2004 Aug;27(8):1317-9.
3,4,5-Trimethoxycinnamic acid (TMCA) is one of the constituents in Onji (roots of Polygala tenuifolia WILLD), an herbal medicine used for sedative in Japanese traditional Kampo medicine. Our previous study revealed that oral administration of this compound prolongs sleeping time induced by hexobarbital in mice to exhibit sedative action. In the present study, we investigate the effects of TMCA on the stress induced with repeated cold exposure or intracerebroventricular injection of corticotrophin-releasing hormone (CRH). Both types of stress significantly reduced the sleeping time induced with pentobarbital in rat, which was significantly prolonged by intraperitoneal injection of TMCA. The intracerebroventricular injection of CRH significantly augmented the content of norepinephrine (NE) in locus coeruleus (LC) of rats, which was significantly suppressed by the intracerebroventricular injection of TMCA. These findings suggest that TMCA would exhibit sedative effects by suppressing NE content in LC.
