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140-10-3 - trans-Cinnamic acid, 99+% - trans-3-Phenylacrylic acid - A13538 - Alfa Aesar

A13538 trans-Cinnamic acid, 99+%

CAS-Nummer
140-10-3
Synonyme
trans-3-Phenylacrylic acid

Größe Preis ($) Menge Verfügbarkeit
100g 22,28
500g 70,25
2500g 222,56
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trans-Cinnamic acid, 99+%

MDL
MFCD00004369
EINECS
205-398-1

Chemische Eigenschaften

Formel
C9H8O2
Molmasse
148.16
Schmelzpunkt
133-136°
Siedepunkt
147°/4mm
Flammpunkt
166°(330°F)
Dichte
1.250
Löslichkeit
Soluble in many organic solvents. Slightly soluble in water.

Anwendungen

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.

Bemerkungen

Incompatible with strong oxidizing agents.

Literaturverweise

Heating with excess thionyl chloride and a catalytic amount of pyridine gives a benzo[b]thiophene derivative, formed by electrophilic addition of thionyl chloride across the double bond of cinnamoyl chloride, Pummerer rearrangement of the resulting sulfinyl chloride and final cyclization. ɑ-Chlorocinnamoyl chloride is formed as a by-product by elimination of SCl2: J. Org. Chem., 40, 3037 (1975):

Under similar conditions, 3-phenylpropionic acid gave the same products in lower yield; the reaction was thought to occur via an initial ɑ-enolization of the acid chloride: Tetrahedron Lett., 5149 (1968).

Bradley, J. C. Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans-cinnamic acid using measured solubilities from the Open Notebook Science Challenge. Chem. Cent. J. 2015, 9 (1), 11.

Wang, H.; Li, Q.; Deng, W.; Omari-siaw, E.; Wang, Q.; Wang, S.; Wang, S.; Cao, X.; Xu, X.; Yu, J. Self-Nanoemulsifying Drug Delivery System of trans-Cinnamic acid: Formulation Development and Pharmacodynamic Evaluation in Alloxan-induced Type 2 Diabetic Rat Model. Drug Dev. Res. 2015, 76 (2), 82-93.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P305+P351+P338

IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Weitere Referenzen

Merck
14,2299
Beilstein
1905952
Harmonized Tariff Code
2916.39
TSCA
Yes
RTECS
GD7850000

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