| Identification | Back Directory | [Name]
3,4,5-TRIMETHOXYCINNAMIC ACID | [CAS]
20329-98-0 | [Synonyms]
AKOS BBS-00000775
RARECHEM BK HC T328
OTAVA-BB BB7119152925
Cinepazide Impurities4
Cinepazide Impurities1390
(E)-3,4,5-Trimethoxycinnamic
3,4,5-Trimethoxycinnamic acid
(E)-3,4,5-Trimethoxycinnamic Acid
trans-3,4,5-TriMethoxycinnaMic acid
3,4,5-Trimethoxy-trans-cinnamic acid
3-(3,4,5-TRIMETHOXYPHENYL)ACRYLIC ACID
3,4,5-TRIMETHOXYCINNAMIC ACID USP/EP/BP
trans-3,4,5-TriMethoxycinnaMic acid
(E)-3-(3,4,5-Trimethoxyphenyl)propenoic acid
(E)-3-(3,4,5-TRIMETHOXY-PHENYL)-ACRYLIC ACID
2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (2E)- | [EINECS(EC#)]
201-999-8 | [Molecular Formula]
C12H14O5 | [MDL Number]
MFCD00004388 | [MOL File]
20329-98-0.mol | [Molecular Weight]
238.24 |
| Chemical Properties | Back Directory | [Melting point ]
125-127 °C(lit.)
| [Boiling point ]
396.4±37.0 °C(Predicted) | [density ]
1.209±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
4.48±0.10(Predicted) | [color ]
White to Light yellow | [InChI]
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+ | [InChIKey]
YTFVRYKNXDADBI-SNAWJCMRSA-N | [SMILES]
C(O)(=O)/C=C/C1=CC(OC)=C(OC)C(OC)=C1 |
| Hazard Information | Back Directory | [Uses]
(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]. | [Definition]
ChEBI: 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. | [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. |
| [IC 50]
5-HT1A Receptor: 7.6 μM (IC50); 5-HT2C Receptor: 2.5 μM (IC50); 5-HT2A Receptor: >10 μM (IC50); 5-HT6 Receptor: >10 μM (IC50); 5-HT7 Receptor: >10 μM (IC50) | [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. DOI:10.1016/j.ejmech.2019.04.009
[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. DOI:10.1016/j.jphs.2015.07.021
[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. DOI:10.1007/s12272-013-0167-6 |
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