4-Hydroxycinnamic acid

Synonym(s):p-Coumaric acid;trans-4-Hydroxycinnamic acid;4-Hydroxycinnamic acid;p-Coumaric acid, p-Cumaric acid

CAS NO.：7400-08-0
Empirical Formula: C9H8O3
Molecular Weight: 164.16
MDL number: MFCD00004399
EINECS: 231-000-0
SAFETY DATA SHEET (SDS)
Update Date: 2025-01-27 09:38:02

What is 4-Hydroxycinnamic acid?

Chemical properties

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

The Uses of 4-Hydroxycinnamic acid

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.

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.

What are the applications of 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.

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

Properties of 4-Hydroxycinnamic acid

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)
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 for 4-Hydroxycinnamic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.