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

A13538 trans-Cinnamic acid, 99+%

CAS Number
140-10-3
Synonyms
trans-3-Phenylacrylic acid

Size Price ($) Quantity Availability
100g 22.28
500g 70.25
2500g 222.56
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trans-Cinnamic acid, 99+%

MDL
MFCD00004369
EINECS
205-398-1

Chemical Properties

Formula
C9H8O2
Formula Weight
148.16
Melting point
133-136°
Boiling Point
147°/4mm
Flash Point
166°(330°F)
Density
1.250
Solubility
Soluble in many organic solvents. Slightly soluble in water.

Applications

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.

Notes

Incompatible with strong oxidizing agents.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: P305+P351+P338

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

Other References

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

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