3,4,5-Trimethoxycinnamic acid Chemical Properties

Melting point:

125-127 °C (lit.)

Boiling point:

300.83°C (rough estimate)

Density 

1.1416 (rough estimate)

vapor pressure 

0-0Pa at 20-25℃

refractive index 

1.4571 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

4.48±0.10(Predicted)

form 

Solid:crystalline

color 

White

BRN 

1537834

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)

InChIKey

YTFVRYKNXDADBI-UHFFFAOYSA-N

SMILES

C(O)(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1

LogP

0.3-1.1 at 35℃ and pH2-7

CAS DataBase Reference

90-50-6(CAS DataBase Reference)

EPA Substance Registry System

2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)- (90-50-6)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

2

RTECS 

GE0722000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29189900

MSDS

• Language:English Provider:3,4,5-Trimethoxycinnamic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,4,5-Trimethoxycinnamic acid Usage And Synthesis

Chemical Properties

white to cream fine crystalline powder

Uses

3-(3,4,5-Trimethoxyphenyl)acrylic acid demonstrates antioxidant activity as it was detected to inhibit lipid peroxidation in rat brain homogenates.

Definition

ChEBI: A methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions.

Synthesis

Example IV Synthesis of 3,4,5-trimethoxycinnamic acid (by microwave radiation method): in a 100 mL Erlenmeyer flask, a mixture of 3,4,5-trimethoxybenzaldehyde (5.0 g, 0.025 mol) and malonic acid (5.30 g, 0.050 mol) was added, followed by piperidine (4-8 mL) and acetic acid (25-35 mL). The flask was fitted with a loose funnel at the top and the mixture was shaken well and placed in a microwave oven and microwaved in batches for 4-8 min. Upon completion of the reaction, the cooled mixture was poured into ice-cold water and acidified with 5% HCl solution. The precipitated yellow solid was collected by filtration and recrystallized by aqueous ethanol to give 3,4,5-trimethoxycinnamic acid in 88% yield; the melting point was 127 °C (literature value 126-128 °C). The spectral data of the product were consistent with those reported in the literature: 1H NMR (CDCl3) δ 7.73 (1H, d, J = 16.0 Hz, -CH=CH-COOH), 6.78 (2H, s, H-2 and H-6), 6.38 (1H, d, J = 16.0 Hz, CH=CH-COOH), 3.91 (9H, s, 3-OCH3, 4- OCH3, 5-OCH3); 13C NMR: δ 172.6 (COOH), 153.8 (C-3 and C-5), 147.4 (C-4), 140.8 (CH=CH-COOH), 129.8 (C-1), 116.8 (CH=CH-COOH), 105.8 (C-2 and C-6), 61.4 (4- OCH3), 56.5 (3-OCH3 and 5-OCH3).

target

5-HT Receptor | ERK | GABA Receptor | HIF-2

References

[1] MedChemComm, 2017, vol. 8, # 4, p. 755 - 766
[2] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 473 - 482
[3] Medicinal Chemistry Research, 2016, vol. 25, # 6, p. 1074 - 1086
[4] Chemistry Letters, 2003, vol. 32, # 12, p. 1186 - 1187
[5] Patent: US2004/118673, 2004, A1. Location in patent: Page 7

3,4,5-Trimethoxycinnamic acid(90-50-6)Related Product Information

• trans-Cinnamic acid
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