3,4,5-Trimethoxycinnamic acid

Names

[ CAS No. ]:
90-50-6

[ Name ]:
3,4,5-Trimethoxycinnamic acid

[Synonym ]:
3,4,5-Trimethoxycinnamic
o-methylsinapicacid
3,4,5-Trimethoxy cinnamic acid
(2E)-3-(3,4,5-Trimethoxyphenyl)acrylic acid
2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (2E)-
3,4,5-Trimethoxycinnamic acid
2-propenoic acid, 3-(3,4,5-trimethoxyphenyl)-
TRIMETHOXYCINNAMICACID
3,4,5-trimethoxy-cinnamicaci
5-TriMethoxycinnaMic acid
3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
EINECS 201-999-8
3,4,5-Trimethoxyzimtsure
RARECHEM BK HC T328
MFCD00004388

Biological Activity

[Description]:

3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifoliaWILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Natural Products >> Phenylpropanoids

Research Areas >> Neurological Disease

[Target]

γ-subunit of GABAA receptor[2]

[In Vitro]

3,4,5-Trimethoxycinnamic acid (10 μg/ml) increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].

[In Vivo]

3,4,5-Trimethoxycinnamic acid (25-100 mg/kg, i.p.) exhibits sedative effect, and prolongs the sleeping time in rats[1]. 3,4,5-Trimethoxycinnamic acid (10 mg/kg, p.o.) significantly decreases locomotor activity in mice[2].

[References]

[1]. Kawashima K, et al. Anti-stress effects of 3,4,5-trimethoxycinnamic acid, an active constituent of roots of Polygala tenuifolia (Onji). Biol Pharm Bull. 2004 Aug;27(8):1317-9.

[2]. 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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
396.4±37.0 °C at 760 mmHg

[ Melting Point ]:
125-127 °C(lit.)

[ Molecular Formula ]:
C₁₂H₁₄O₅

[ Molecular Weight ]:
238.237

[ Flash Point ]:
151.5±20.0 °C

[ Exact Mass ]:
238.084122

[ PSA ]:
64.99000

[ LogP ]:
2.00

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.560

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GE0722000

CHEMICAL NAME :: Cinnamic acid, 3,4,5-trimethoxy-

CAS REGISTRY NUMBER :: 90-50-6

BEILSTEIN REFERENCE NO. :: 1537834

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H14-O5

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 422 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AECTCV Archives of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 070944) V.1- 1973- Volume(issue)/page/year: 12,355,1983

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi: Irritant;

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
GE0722000

[ HS Code ]:
2916399090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916399090

[ Summary ]:
2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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