7778-83-8

Usage

Uses

Used in Flavor and Fragrance Industry:
Propyl cinnamate is used as a flavoring agent for its peach-apricot flavor, adding a pleasant taste to various food products. It is also utilized as a fragrance component in the perfumery industry, where its wine-like odor contributes to the creation of captivating scents.
Used in Insect Repellent Applications:
Propyl cinnamate is used as an insect repellent, taking advantage of its natural properties to ward off insects and provide protection against their bites. This application is particularly useful in outdoor settings and for personal care products designed to keep insects at bay.

Preparation

By esterification of cinnamic acid with propyl alcohol in the presence of HCl as a catalyst; or by direct esterification in the presence of benzene.

InChI:InChI=1/C12H14O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h3-9H,2,10H2,1H3/b9-8+

Upstream product

• 71-23-8 propan-1-ol 
• 73789-34-1 cinnamic acid 4-chlorophenyl ester 
• 540-54-5 1-Chloropropane 
• 621-82-9 Cinnamic acid 
• 109-60-4 1-Propyl acetate 
• 100-52-7 benzaldehyde 
• 102-92-1 cinnamoyl chloride 
• 300-57-2 allylbenzene 
• 591-50-4 iodobenzene 
• 925-60-0 n-propyl acrylate 
• 104-55-2 3-phenyl-propenal 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 56289-55-5 allyl cinnamate 

Downstream Products

• 103-26-4 methyl cinnamate 
• 1621106-08-8 propyl 4-phenyl-3-(p-tolyl)isoxazole-5-carboxylate 
• 1621105-94-9 C₁₂H₁₃N₃O₂ 
• 52392-64-0 n-butyl cinnamate 
• 13326-06-2 n-propyl 3-phenylpropionate 

Relevant academic research and scientific papers

DBU-Based Dicationic Ionic Liquids Promoted Esterification Reaction of Carboxylic Acid with Primary Chloroalkane Under Mild Conditions

Abstract: A series of DBU-based (DBU = 1, 8-diazabicyclo [5.4.0] undec-7-ene) dicationic ionic liquids with different anions were successfully synthesized by the reaction of DBU and 1, 6-dichlorohexane. Therein, the dicationic ionic liquid 1, 1′-(hexane-1, 6-diyl)bis(1, 8-diazabicyclo [5.4.0]undec-7-enium) dichlorine (IL-1) was successfully employed as an efficient catalyst in esterification reaction of carboxylic acids with primary chloroalkanes under mild conditions without any additional basic reagents. Moreover, the optimum catalyst could be efficiently reused for five times without any significant change on the catalytic effect. The improved protocol is not only efficient, but also green and pollution-free.

An ionic liquid catalyzed probase method for one-pot synthesis of α,β-unsaturated esters from esters and aldehydes under mild conditions

A one-pot synthesis of α,β-unsaturated esters from unactivated esters and aldehydes using strong bases, such as sodium alkoxide and potassium tert-butoxide, was reported. However, the ionic liquid (IL) catalyzed probase method for producing α,β-unsaturated esters was not reported until now. In this work, a series of ILs with fluoride anions were firstly prepared and used as catalysts in combination with the probase N,O-bis(trimethylsilyl) acetamide (BSA) for the α,β-unsaturated esters synthesis. This process could also be promoted through the introduction of another IL with Lewis acid sites. The yield and selectivity of the product could reach up to 84.2% and 95.0%, respectively, when [Bmim]F was used in combination with [Bmim]Cl/AlCl3 (the molar fraction of AlCl3 is 0.67). The mechanism investigation through GC-MS indicates that BSA would convert into onium amide, which acted as a strong base for α-H abstraction, with the catalysis of [Bmim]F. Meanwhile, [Bmim]Cl/AlCl3 played an important role in the condensation step between enolates and aldehydes. On the basis of mechanism insights, kinetic and thermodynamic studies were also carried out for a better understanding of this new route.

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection

A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.

Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain

Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r2 = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.

Palladium-catalyzed aerobic oxidative double allylic C-H oxygenation of alkenes: A novel and straightforward route to α,β-unsaturated esters

A mild tandem oxidative functionalization of allyl aromatic hydrocarbons was accomplished using the catalytic system of Pd(OAc)2/DMA under 1 atm O2. The green twofold C-O bond formation involving double allylic C-H oxygenation unlocks opportunities for markedly different synthetic strategies. Moreover, the reaction affords aryl α,β-unsaturated esters directly from readily available terminal olefins in moderate to good yields with excellent chemo- and stereoselectivities.

Sustainable carbonecarbon bond formation catalyzed by new oxamate-containing palladium(II) complexes in ionic liquids

New and versatile bis(oxamato)palladate(II) complexes of formula (n-Bu 4N)2[Pd(2-Mepma)2]·4H2O (1a) and (n-Bu4N)2[Pd(4-Mepma)2]·2H 2O·MeCN (1b) (n-Bu4N+ = tetra-n-buthylammonium, 2-Mepma = N- 2-methylphenyloxamate and 4-Mepma = N-4-methylphenyloxamate) have been synthesized and characterized by spectroscopic methods and single crystal X-ray diffraction. Each palladium(II) ion in 1a and 1b is four-coordinate with two oxygen and two nitrogen atoms from two fully deprotonated oxamate ligands building a centrosymmetric square planar surrounding. Their catalytic role has been investigated for both Heck and Suzuki coupling reactions using a series of aryl iodide/bromide derivatives in tetra-n-butylammonium bromide (n-Bu 4NBr) as ionic liquid, i.e. molten salt. These precatalysts appear as highly efficient, easily recovered and reused at least eight times without any drastic loss of their exceptional reactivity or leaching from the ionic liquid medium.

Manganese phthalocyanine immobilized on silica gel: Efficient and recyclable catalyst for single-step oxidative esterification of aldehydes with alcohols

The functionalization of silica gel was carried out using 3-aminopropyltriethoxysilane as a reactive surface modifier followed by covalent grafting of novel tetrakis-(2-methoxy-4-formylphenoxy)phthalocyaninato manganese(III) acetate complex. The resulting inorganic-organic hybrid material was found to be a highly selective and recyclable catalyst for the single-step synthesis of esters. The catalyst was characterized by elemental analysis (CHN), diffuse reflectance UV-visible, 13C CPMAS and 29Si CPMAS NMR spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), BET surface area analysis, energy dispersive X-ray fluorescence (ED-XRF), Fourier-transform infrared (FT-IR) and atomic absorption spectroscopy (AAS) techniques, which demonstrates the covalent grafting of the complex onto functionalized silica gel. The catalytic performance of the novel inorganic-organic hybrid catalyst was evaluated in the direct oxidative esterification of aldehydes with alcohols, at ambient temperature, using hydrogen peroxide as an environment friendly oxidant. The hybrid catalyst presented up to 100% of substrate conversion with high turn-over numbers (TONs), up to 100% of selectivity toward the ester product, and can be recovered and reused for multiple cycles without appreciable loss in its catalytic activity.

Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-α induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3′,4′,5′-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-α induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-α induced adhesion of neutrophils to the endothelial monolayer. Structure-activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the α, β- C-C double bond in the thiocinnamates and thionocinnamates.

Br?nsted acidic ionic liquid as an efficient and recyclable promoter for hydroesterification of olefins catalyzed by a triphenylphosphine-palladium complex

Several Br?nsted acidic ionic liquids (BAILs) with different acidic scales were synthesized and employed as acid promoters for the hydroesterification of olefins catalyzed by a triphenylphosphine-palladium complex. The results showed that catalysts with BAIL promoters resulted inmoderate to high conversions to the ester product with excellent selectivity, depending on the acidity of BAIL used. The reaction conversion reached a plateau when the catalyst was promoted using BAIL with a Hammett acidity function less than or equal to-0.11. This catalyst system could be reused several times for the hydroesterification of 1-hexene without a considerable decrease in the catalytic performance.

Nucleophilic iron catalysis in transesterifications: Scope and limitations

Figure presented The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.