trans-Cinnamic acid

Description

Cinnamic acid exists as trans and cis isomers, but the trans form is the one most often found in nature and is the article of commerce. It is obtained from cinnamon bark and balsam resins such as storax. It was first isolated in 1872 by F. Beilstein (of?Handbook of Organic Chemistry?fame) and A. Kuhlberg. It is synthesized by the Perkin reaction between Ac2O and PhCHO.
trans-Cinnamic acid is used in the manufacture of flavors, dyes, and pharmaceuticals; but its major use is for the production of its methyl, ethyl, and benzyl esters. These esters are important components of perfumes. The acid is also a precursor to the sweetener aspartame.
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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.

The Uses of trans-Cinnamic acid

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.

The Uses of trans-Cinnamic acid

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

What are the applications of Application

trans-Cinnamic acid is A biochemical used to establish library of phenolic compounds.

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.]