3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID Chemical Properties

Melting point:

100-104 °C (lit.)

Boiling point:

373℃

Density 

1.169

refractive index 

1.5140 (estimate)

Flash point:

140℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

form 

Crystalline Powder

pka

4.70±0.10(Predicted)

color 

White to almost white

BRN 

1471912

InChI

InChI=1S/C12H16O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h6-7H,4-5H2,1-3H3,(H,13,14)

InChIKey

ZCYXGVJUZBKJAI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

25173-72-2(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID Usage And Synthesis

Chemical Properties

WHITE TO ALMOST WHITE CRYSTALLINE POWDER

Uses

3-(3,4,5-Trimethoxyphenyl)propanoic acid is found in herbs and spices. 3-(3,4,5-Trimethoxyphenyl)propanoic acid is a constituent of Piper longum (long pepper) and Piper retrofractum (Javanese long pepper).

Definition

ChEBI: A monocarboxylic acid consisting of propionic acid having a 3,4,5-trimethoxyphenyl substituent at the 3-position.

Synthesis

General procedure for the synthesis of 3-(3,4,5-trimethoxyphenyl)propionic acid from (E)-3-(3,4,5-trimethoxyphenyl)propenoic acid (by microwave radiation method): in a 100 mL Erlenmeyer flask, 3,4,5-trimethoxycinnamic acid (0.72 g, 0.003 mol) and PdCl2 (55 mg, 0.31 mmol) were suspended in 10% sodium hydroxide solution (6-10 mL), followed by batchwise addition of formic acid (8-12 mL). The mixture was reacted under microwave radiation for 3-5 min until the feedstock completely disappeared. Upon completion of the reaction, the cooled mixture was poured into ice water, acidified with 5% HCl and extracted with dichloromethane (3 x 10 mL). The organic layer was washed with water and dried with anhydrous Na2SO4. The solvent was removed by evaporation and the crude product was recrystallized by a solvent mixture of ethyl acetate and hexane to give 3-(3,4,5-trimethoxyphenyl)propionic acid as a white solid in 84% yield with a melting point of 102 °C (literature value 101-102 °C).1H NMR (CDCl3) δ: 6.70 (2H, s, H-2 and H-6), 3.84 (9H, s, 3-OCH3,4- OCH3 and 5-OCH3), 2.92 (2H, t, Ar-CH2-CH2-COOH), 2.70 (2H, t, -CH2-CH2-COOH); 13C NMR δ: 178.1 (COOH), 153.1 (C-3 and C-5), 135.87 (C-4 and C-1), 105.3 (C-2 and C-6) , 60.8 (4-OCH3), 56.1 (3-OCH3 and 5-OCH3), 35.5 (Ar-CH2-), 31.0 (-CH2-COOH).

IC 50

Human Endogenous Metabolite

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 11953 - 11962
[2] Chemistry Letters, 2003, vol. 32, # 12, p. 1186 - 1187
[3] Patent: US2004/118673, 2004, A1. Location in patent: Page 7
[4] Bioorganic Chemistry, 2018, vol. 80, p. 408 - 421
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7785 - 7788

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