[CAS NO. 20329-98-0] (E)-3,4,5-Trimethoxycinnamic acid
PRODUCTS SPECIFICATIONS [20329-98-0]
DESCRIPTION [20329-98-0]
Overview
| MDL | MFCD00004388 |
|---|---|
| Molecular Weight | 238.24 |
| Molecular Formula | C12H14O5 |
| SMILES | O=C(O)/C=C/C1=CC(OC)=C(OC)C(OC)=C1.[(E)] |
Summary
(E)-3,4,5-Trimethoxycinnamic acid (TMCA) is a cinnamic acid substituted by multi-methoxy groups. (E)-3,4,5-Trimethoxycinnamic acid is an orally active and potent GABA A /BZ receptor agonist. (E)-3,4,5-Trimethoxycinnamic exhibits favourable binding affinity to 5-HT 2C and 5-HT 1A receptor, with IC 50 values of 2.5 and 7.6 μM, respectively. (E)-3,4,5-Trimethoxycinnamic acid shows anticonvulsant and sedative activity. (E)-3,4,5-Trimethoxycinnamic acid can be used for the research of insomnia, headache and epilepsy [1] [2] [3] .
In Vitro
(E)-3,4,5-Trimethoxycinnamic acid (10 μg/mL, 1 h) increases the expressions of GAD
65
and γ-subunit of GABA
A
receptors in the cerebellar granule cells
[3]
.
(E)-3,4,5-Trimethoxycinnamic acid (0-10 μg/mL, 1 h) shows a significant increase in Cl
-
influx
[3]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Western Blot Analysis [3]
| Cell Line: | Primary cultured cerebellar granule cells |
| Concentration: | 10 μg/mL |
| Incubation Time: | 1 h |
| Result: | Increased expression of GAD 65 (glutamic acid decarboxylase) and γ-subunit of GABAA receptors, but did not influence the amounts of a-, b-subunits in the GABAA receptors. |
Cell Viability Assay [3]
| Cell Line: | Primary cultured cerebellar granule cells |
| Concentration: | 1, 3, 5, 10 μg/mL |
| Incubation Time: | 1 h |
| Result: | Produced a significant increase in Cl - influx. |
In Vivo
(E)-3,4,5-Trimethoxycinnamic acid (0-20 mg/kg, IP, once) shows anti-seizure effects
[2]
.
(E)-3,4,5-Trimethoxycinnamic acid (0-10 mg/kg, Orally, once) enhances hypnotic effects in pentobarbital-treated mice
[3]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| Animal Model: | Ault male KunMing-strain mice (18-20 g, maximal electroshock (MES) and pentylenetetrazol (PTZ) models) [2] |
| Dosage: | 5, 10 and 20 mg/kg; 10 mL/kg |
| Administration: | IP, once |
| Result: | Significantly decreased the incidence of MES-induced THE (tonic hindlimb extension) to 50% and 20% of the value of the vehicle controls at 10 and 20 mg/kg. Decreased the incidence of MES-induced THE to only 80% at 5 mg/kg. Significantly delayed the onset of myoclonic jerks (MJ), and decreased the seizure severity and mortality compared with the vehicle-treated animals in PTZ seizure model. The incidence of generalized clonic convulsions (stage 4) disappeared at doses of both 10 and 20 mg/kg. |
| Animal Model: | ICR male mice (25-28 g, 10-12 in each group) [3] |
| Dosage: | 2, 5 and 10 mg/kg |
| Administration: | Orally (p.o.), once, 15 min and 1 h prior to pentobarbital injection |
| Result: | Significantly decreased locomotor activity at 10 mg/kg. Increased NREM and total sleep, but decreased wakefulness. |
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT03929913 | National Heart, Lung, and Blood Institute (NHLBI)|National Institutes of Health Clinical Center (CC) |
Functional Mitral Regurgitation
|
May 7, 2019 | Not Applicable |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : 100 mg/mL ( 419.74 mM ; Need ultrasonic)
Stock Solutions
| Concentration Solvent Mass | 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 |
References
- [1] Zhao Z, et al. 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] Chen CY, et al. 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] Lee CI, et al. 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.
Synonyms