4-METHOXYCINNAMIC ACID Chemical Properties

Melting point:

173.5 °C(lit.)

Boiling point:

342.6±17.0 °C(Predicted)

Density 

1.195±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in ethanol, ethyl acetate and other organic solvents.

pka

4.60±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

BRN 

510468

InChIKey

AFDXODALSZRGIH-QPJJXVBHSA-N

LogP

1.264 (est)

CAS DataBase Reference

943-89-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoic acid, 3-(4-methoxyphenyl)-, (e)-(943-89-5)

EPA Substance Registry System

2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)- (943-89-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

UD3391300

F 

8

TSCA 

Yes

HS Code 

2918.29.7500

HazardClass 

IRRITANT

MSDS

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

4-METHOXYCINNAMIC ACID Usage And Synthesis

Uses

Esters derived from trans-4-methoxycinnamic acid are effective absorbers of UV radiation. The starting material was trans-4-methoxycinnamic acid and 3,5dimethoxybenzoic acid methyl ester in isolated avenanthramide alkaloids synthsis. trans-4-Methoxycinnamic acid was converted into its acid chloride (yield 98%) with thionyl chloride. Employed in organic synthesis of pharmaceutical intermediates, synthetic anti-adrenergic drugs esmolol, cosmetics ultraviolet absorption.

Preparation

4-methoxycinnamic acid synthesis : In a 25-mL, roundbottomed flask, 4-methoxybenzaldehyde (0.804 mL, 6.61 mmol) (3), malonic acid (1.75 g, 16.8 mmol), and β-alanine (0.10 g, 1.12 mmol) were dissolved in pyridine (3.0 mL, 37.1 mmol) and heated under reflux for 90 minutes. After cooling to room temperature, the reaction mixture was placed in an ice bath and 8.0 mL of concentrated HCl was slowly added. The resulting white precipitate was collected by vacuum filtration, washed with cold water (2 x 10mL) and dried thoroughly. The product was recrystallized from absolute ethanol (~20 mL).
Synthesis of 4-methoxycinnamic acid

Definition

ChEBI: 4-methoxycinnamic acid is a methoxycinnamic acid having a single methoxy substituent at the 4-position on the phenyl ring. It is functionally related to a cinnamic acid.

Purification Methods

Crystallise the acid from MeOH to constant melting point and UV spectrum. [Beilstein 10 IV 1005.]

4-METHOXYCINNAMIC ACID(943-89-5)Related Product Information

• trans-Cinnamic acid
• Octyl 4-methoxycinnamate
• Fumaric acid
• TRANS-1,2-DIAMINOCYCLOHEXANE-N,N,N',N'-TETRAACETIC ACID MONOHYDRATE
• trans-Ferulic acid
• TRANS-ACONITIC ACID
• trans-2-Hexenoic acid
• 4-Methoxycinnamic acid