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

A13538 trans-Cinnamic acid, 99+%

Número CAS
140-10-3
Nombre Alternativo
trans-3-Phenylacrylic acid

Tamaño Precio ($) Cantidad Disponibilidad
100g 22,00
500g 68,90
2500g 274,00
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trans-Cinnamic acid, 99+%

MDL
MFCD00004369
EINECS
205-398-1

Propiedades químicas

Fórmula
C9H8O2
Peso molecular
148.16
Punto de fusión
133-136°
Punto de ebullición
147°/4mm
Punto de inflamabilidad
166°(330°F)
Densidad
1.250
Solubilidad
Soluble in many organic solvents. Slightly soluble in water.

Aplicaciones

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.

Notas

Incompatible with strong oxidizing agents.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H315-H319-H335

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

Indicaciones de precaución: P305+P351+P338

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

Otras referencias

Merck
14,2299
Beilstein
1905952
Código de tarifa arancelaria unificado
2916.39
TSCA
Yes
RTECS
GD7850000

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