Introduction：Basic information about CAS 20329-98-0|3,4,5-Trimethoxy-trans-cinnamic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 3,4,5-Trimethoxy-trans-cinnamic acid |
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| CAS Number | 20329-98-0 | Molecular Weight | 238.237 |
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| Density | 1.2±0.1 g/cm3 | Boiling Point | 396.4±37.0 °C at 760 mmHg |
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| Molecular Formula | C12H14O5 | Melting Point | 125-127ºC(lit.) |
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| MSDS | / | Flash Point | 151.5±20.0 °C |
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Names
| Name | 3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid |
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| Synonym | More Synonyms |
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3,4,5-Trimethoxy-trans-cinnamic acid BiologicalActivity
| Description | (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 GABAA/BZ receptor agonist. (E)-3,4,5-Trimethoxycinnamic exhibits favourable binding affinity to 5-HT2C and 5-HT1A receptor, with IC50 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]. |
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| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>GABA ReceptorResearch Areas >>Neurological DiseaseSignaling Pathways >>Neuronal Signaling >>GABA ReceptorSignaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling Pathways >>Neuronal Signaling >>5-HT Receptor |
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| In Vitro | (E)-3,4,5-Trimethoxycinnamic acid (10 μg/mL, 1 h) increases the expressions of GAD65 and γ-subunit of GABAA 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]. Western Blot Analysis[3] Cell Line: Primary cultured cerebellar granule cells Concentration: 10 μg/mL Incubation Time: 1 h Result: Increased expression of GAD65 (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. |
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| 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]. 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. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
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| Boiling Point | 396.4±37.0 °C at 760 mmHg |
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| Melting Point | 125-127ºC(lit.) |
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| Molecular Formula | C12H14O5 |
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| Molecular Weight | 238.237 |
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| Flash Point | 151.5±20.0 °C |
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| Exact Mass | 238.084122 |
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| PSA | 64.99000 |
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| LogP | 2.00 |
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| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
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| Index of Refraction | 1.560 |
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| InChIKey | YTFVRYKNXDADBI-SNAWJCMRSA-N |
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| SMILES | COc1cc(C=CC(=O)O)cc(OC)c1OC |
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Safety Information
| Safety Phrases | 24/25 |
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| WGK Germany | 2 |
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| RTECS | GE0722000 |
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Synonyms
| O-Methylsinapic acid |
| 3,4,5-Trimethoxycinnamic_acid |
| (E)-6,7,8-trimethoxycinnamic acid |
| (2E)-3-(3,4,5-Trimethoxyphenyl)acrylic acid |
| 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (2E)- |
| 3,4,5-Trimethoxycinnamic acid |
