Basic information Safety Supplier Related

3,4,5-TRIMETHOXYCINNAMIC ACID

Basic information Safety Supplier Related

3,4,5-TRIMETHOXYCINNAMIC ACID Basic information

Product Name:
3,4,5-TRIMETHOXYCINNAMIC ACID
Synonyms:
  • (E)-3-(3,4,5-TRIMETHOXY-PHENYL)-ACRYLIC ACID
  • AKOS BBS-00000775
  • 3-(3,4,5-TRIMETHOXYPHENYL)ACRYLIC ACID
  • (E)-3-(3,4,5-Trimethoxyphenyl)propenoic acid
  • 3,4,5-Trimethoxycinnamic acid
  • OTAVA-BB BB7119152925
  • RARECHEM BK HC T328
  • trans-3,4,5-TriMethoxycinnaMic acid
CAS:
20329-98-0
MF:
C12H14O5
MW:
238.24
EINECS:
201-999-8
Mol File:
20329-98-0.mol
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3,4,5-TRIMETHOXYCINNAMIC ACID 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
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
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Safety Information

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

MSDS

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3,4,5-TRIMETHOXYCINNAMIC ACID 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-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

3,4,5-TRIMETHOXYCINNAMIC ACIDSupplier

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