3,4,5-TRIMETHOXYCINNAMIC ACID

Product Name3,4,5-TRIMETHOXYCINNAMIC ACID
CAS20329-98-0
MFC12H14O5
MW238.24
EINECS201-999-8
MOL File20329-98-0.mol

Chemical Properties

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
pka	4.48±0.10(Predicted)
form	powder to crystal
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

Safety Information

Safety Statements	24/25
WGK Germany	2
RTECS	GE0722000
HS Code	2918.99.4700

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

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-HT_1A Receptor: 7.6 μM (IC₅₀); 5-HT_2C Receptor: 2.5 μM (IC₅₀); 5-HT_2A 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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