2-Methoxycinnamic acid Chemical Properties

Melting point:

182-186 °C

Boiling point:

250.41°C (rough estimate)

Density 

1.1479 (rough estimate)

refractive index 

1.5088 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

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

form 

powder

pka

pK1:4.462 (25°C)

color 

White

BRN 

2209714

InChI

InChI=1S/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12)

InChIKey

FEGVSPGUHMGGBO-UHFFFAOYSA-N

SMILES

C(O)(=O)C=CC1=CC=CC=C1OC

LogP

2.418 (est)

CAS DataBase Reference

6099-03-2(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoic acid, 3-(2-methoxyphenyl)-(6099-03-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29189900

MSDS

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

2-Methoxycinnamic acid Usage And Synthesis

Chemical Properties

light yellow crystalline powder

Uses

(E)-3-(2-Methoxyphenyl)acrylic Acid is a noncompetitive inhibitor of tyrosinase.

Definition

ChEBI: (E)-2-methoxycinnamic acid is a member of the class of cinnamic acids that is trans-cinnamic acid carrying a methoxy substituent at position 2 on the benzene ring. It has a role as a Brassica napus metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a member of cinnamic acids and a monomethoxybenzene. It is functionally related to a trans-cinnamic acid.

Synthesis

To a 500 mL three-necked round-bottomed flask was added o-methoxybenzaldehyde (20 g, 146.90 mmol, 1.00 eq.), pyridine (250 mL), malonic acid (18.3 g, 175.86 mmol, 1.20 eq.) and piperidine (2.5 g, 29.36 mmol, 0.20 eq.). The reaction mixture was stirred at 85°C overnight. Upon completion of the reaction, most of the solvent was removed by distillation under reduced pressure, followed by adjusting the pH of the remaining solution with aqueous hydrochloric acid to 3.0. The precipitated solid was collected by filtration to afford 25.6 g (98% yield) of 2-methoxycinnamic acid as a white solid.

References

[1] Patent: WO2014/182950, 2014, A1. Location in patent: Paragraph 00322; 00323
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 336 - 343
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 187 - 191
[4] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4513 - 4519

2-Methoxycinnamic acid(6099-03-2)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• trans-Cinnamic acid
• alpha-Methylcinnamic acid
• N-BUTYL CINNAMATE
• Ethyl cinnamate
• 4-Hydroxycinnamic acid
• Folic acid
• Methyl cinnamate
• Acrylic acid
• Cinnamic acid
• o-Anisic acid
• o-Anisaldehyde
• Citric acid
• Ascoric Acid
• 3,4-Dimethoxycinnamonitrile
• 3,4,5-Trimethoxycinnamic acid
• 3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID
• 3-HYDROXY-4-METHOXYCINNAMIC ACID