trans-Cinnamic acid Chemical Properties

Melting point:

133 °C (lit.)

Boiling point:

300 °C(lit.)

Density 

1.248

vapor pressure 

1.3 hPa (128 °C)

refractive index 

1.5049 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

0.4g/l

pka

4.44(at 25℃)

form 

Crystalline Powder

color 

White to almost white

Specific Gravity

0.91

Odor

Faint odour

PH Range

3 - 4

PH

3-4 (0.4g/l, H2O, 20℃)

Odor Type

balsamic

Water Solubility 

0.4 g/L (20 ºC)

λmax

273nm(MeOH)(lit.)

Merck 

14,2299

BRN 

1905952

Stability:

Light Sensitive

InChIKey

WBYWAXJHAXSJNI-VOTSOKGWSA-N

LogP

2.130

CAS DataBase Reference

140-10-3(CAS DataBase Reference)

NIST Chemistry Reference

Cinnamic acid(140-10-3)

EPA Substance Registry System

(E)-Cinnamic acid (140-10-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

1

RTECS 

GD7850000

TSCA 

Yes

HS Code 

29163900

Toxicity

LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg

MSDS

• Language:English Provider:3-Phenyl-2-propenoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

trans-Cinnamic acid Usage And Synthesis

Chemical Properties

White to almost white crystalline powder. Insoluble in water, slightly soluble in hot water, easily soluble in benzene, acetone, ether, glacial acetic acid and other organic solvents.

Uses

trans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.

Uses

trans-Cinnamic acid was used to establish library of phenolic compounds by liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry.

Definition

ChEBI: Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of styrenes and a member of cinnamic acids. It is a conjugate acid of a cinnamate.

General Description

trans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. It is mainly used to prepare ester derivatives that are used in perfume industry. trans-Cinnamic acid is the key volatile components of cinnamon essential oil.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

trans-cinnamic acid has inhibitory effect on phorbol-12-myristate-13-acetate-induced invasion of human lung adenocarcinoma A549 cells. It is a potential agent which can prevent lung tumor cells from metastasizing. It induces intracellular release of Ca2+ from the vacuole to the cytoplasm which triggers phytotoxicity in cucumber.

Purification Methods

Crystallise the acid from *benzene, CCl4, hot water, water/EtOH (3:1), or 20% aqueous EtOH. Dry it at 60o in vacuo. It is steam volatile. [Beilstein 9 IV 2002.]

trans-Cinnamic acid(140-10-3)Related Product Information

• Acrylic acid
• 4-Methoxycinnamic acid
• Methyl propiolate
• 3-(Trifluoromethyl)cinnamic acid
• trans,trans-2,4-Undecadienal
• Methyl acrylate
• Methacrylic acid
• Diphenyl ether
• Phenyl salicylate
• 6-Benzylaminopurine
• Methyl methacrylate
• Butyl acrylate
• Poly(acrylic acid)
• PHENYL VALERATE
• Methyl cinnamate
• Ethyl acrylate
• trans-Cinnamic acid allyl ester
• Cinnamaldehyde