4-Hydroxycinnamic acid Chemical Properties

Melting point:

214 °C (dec.)(lit.)

Boiling point:

251.61°C (rough estimate)

Density 

1.2132 (rough estimate)

refractive index 

1.5380 (estimate)

storage temp. 

Store below +30°C.

solubility 

Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.65±0.10(Predicted)

color 

White to Off-White

Stability:

Light Sensitive

InChI

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)

InChIKey

NGSWKAQJJWESNS-UHFFFAOYSA-N

SMILES

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

LogP

1.790

CAS DataBase Reference

7400-08-0(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoic acid, 3-(4-hydroxyphenyl)-(7400-08-0)

EPA Substance Registry System

p-Hydroxycinnamic acid (7400-08-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-22

WGK Germany 

2

RTECS 

GD9095000

HS Code 

2918 29 00

MSDS

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

4-Hydroxycinnamic acid Usage And Synthesis

Chemical Properties

Light yellow to beige crystalline powder with aroma, soluble in methanol, ethanol, DMSO and other organic solvents, derived from synthesis.

Uses

4-Hydroxycinnamic acid is the hydroxy derivative of Cinnamic Acid with antioxidant properties. It is a is a major component of lignocellulose. Studies suggest that 4-Hydroxycinnamic acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines. A recent study reports that 4-Hydroxycinnamic acid may act as a chemical castrator in bees by altering the epression of genes required for ovary development. This compound is common in pollen a major constituent of the worker bee diet, but it is not found in queen bees'royal jelly.

Application

p-Hydroxycinnamic acid is mainly used as an intermediate in the pharmaceutical and perfume industries. It can react with dimethyl sulfate to produce p-anisaldehyde, react with acetaldehyde to produce p-hydroxycinnamaldehyde, and further oxidize it to produce cinnamic acid. This product can be directly oxidized to produce 4-Hydroxybenzoic acid and reduction to produce 4-Hydroxybenzyl alcohol.

Definition

ChEBI: 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.

Hazard

Moderately toxic.

Safety Profile

Moderarely toxic by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes. See also COUMARIN

4-Hydroxycinnamic acid(7400-08-0)Related Product Information

• p-Coumaric acid
• Methyl 4-hydroxyphenylacetate
• Methyl 3-(4-hydroxyphenyl)propionate
• Sodium methylparaben
• Sodium propylparaben
• 4-Hydroxybenzoic acid
• 4-Nitrophenylacetic acid
• 3-(4-Hydroxyphenyl)propionic acid
• 4-Nitrobenzyl alcohol
• 4-Bromomethylbenzoic acid
• 4'-Hydroxyacetophenone
• 4-Formylbenzoic acid
• 4-Nitrobenzaldehyde
• 4-Ethoxybenzoic acid
• 3,5-DI-T-BUTYL-4-HYDROXYCINNAMIC ACID,3,5-DI-TERT-BUTYL-4-HYDROXYCINNAMIC ACID
• 4-Hydroxyphenylpyruvic acid
• HYDROXYCINNAMIC ACID
• Ferulic Acid