122-68-9

Basic information

• Product Name: 3-PHENYLPROPYL CINNAMATE
• Synonyms: 3-phenyl-2-propenoicacid3-phenylpropylester;3-Phenylproylcinnamate;cinnamicacid,3-phenylpropylester;phenylpropylcinnamate;3-Phenylpropylcinnamat;3-Phenylacrylic acid 3-phenylpropyl ester;B-PHENYLPROPYL CINNAMATE;FEMA 2894
• CAS NO: 122-68-9
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.33
• EINECS: 204-565-6
• Mol File: 122-68-9.mol

Chemical Properties

• Boiling Point: 420℃
• Flash Point: 261℃
• Appearance: colorless clear liquid
• Density: 1.091
• Vapor Pressure: 2.87E-07mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• CAS DataBase Reference: 3-PHENYLPROPYL CINNAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLPROPYL CINNAMATE(122-68-9)
• EPA Substance Registry System: 3-PHENYLPROPYL CINNAMATE(122-68-9)

Safety Data

• Hazardous Substances Data: 122-68-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
3-PHENYLPROPYL CINNAMATE is used as a flavoring agent for its sweet, cocoa-like taste. It is commonly utilized in the creation of various food products to enhance their flavor profile.
3-PHENYLPROPYL CINNAMATE is also used as a fragrance ingredient for its sweet, heavy, floral-fruity odor with a balsamic note. It is widely employed in the perfumery industry to add depth and complexity to fragrance compositions.
Used in Cosmetics and Personal Care Industry:
In the cosmetics and personal care industry, 3-PHENYLPROPYL CINNAMATE is used as a fixative agent in perfumes and colognes. Its ability to provide a balsamic note and enhance the longevity of fragrances makes it a valuable component in the formulation of personal care products.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 3-PHENYLPROPYL CINNAMATE could potentially be used in the pharmaceutical industry as an active ingredient or additive in the development of medications, given its sweet flavor and pleasant odor. Further research and development would be required to explore its potential applications in this field.

Preparation

From phenylpropyl alcohol and methylcinnamate.

InChI:InChI=1/C18H18O2/c19-18(14-13-17-10-5-2-6-11-17)20-15-7-12-16-8-3-1-4-9-16/h1-6,8-11,13-14H,7,12,15H2/b14-13-

Upstream product

• 122-97-4 3-Phenyl-1-propanol 
• 42893-53-8 S-ethyl thiocinnamate 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 140-10-3 (E)-3-phenylacrylic acid 
• 4136-95-2 2,4,6-trichlorobenzoyl chloride 
• 14371-10-9 (E)-3-phenylpropenal 
• 344414-37-5 cinnamoyl 2,4,6-trichlorobenzoyl mixed anhydride 
• 434935-69-0 2-methyl-6-nitrobenzoic anhydride 
• 637-59-2 1-Bromo-3-phenylpropane 
• 621-82-9 Cinnamic acid 
• 104-55-2 3-phenyl-propenal 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 

Relevant articles and documents

Convenient and Simple Esterification in Continuous-Flow Systems using g-DMAP

The utility and applicability of polyethylene-g-polyacrylic acid-immobilized dimethylaminopyridine (g-DMAP) as a catalyst in a continuous-flow system were investigated for decarboxylative esterification. High catalytic activity toward acylation was provided by g-DMAP containing a flexible grafted-polymer structure. During decarboxylation, carboxylic acids and alcohols were converted cleanly using di-tert-butyl dicarbonate (Boc2O) as a coupling reagent, which reduced by-products. In addition, the use of Boc2O resulted in the formation of tert-butyl esters. These esterifications dramatically reduced the reaction time under continuous-flow conditions, with a residence time of approximately 2 min. This highly efficient esterification procedure will provide more practical industrial applications.

N-heterocyclic carbene catalysed oxidative coupling of aldehydes with alcohols/thiols and one-pot oxidation/esterification of allylic alcohols

A versatile carbene-catalysed oxidation protocol involving N-heterocyclic carbene catalysts and 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) is described for the synthesis of esters, cinnamic acids, and thioesters. A wide range of esters, thioesters, and cinnamic acids were obtained by metal-free coupling of aldehydes with aliphatic, allylic and aromatic alcohols, benzyl mercaptan, and water. In addition to the oxidative coupling of aldehydes with nucleophiles, dehydrogenation of saturated aldehydes and oxidation of allylic alcohols were found under our oxidative coupling conditions. Unlike other TEMPO-mediated oxidative esterification reactions, this reaction does not proceed through a TEMPO ester intermediate to form esters and thioesters. N-Heterocyclic carbene complexes catalyse various oxidative coupling reactions in the presence of TEMPO. A variety of α,β-unsaturated and saturated esters, and aromatic esters and thioesters were synthesised. Copyright

NHC-catalyzed C-O or C-N bond formation: Efficient approaches to α,β-unsaturated esters and amides

Simple and efficient NHC-catalyzed transformations of bromoenal or α,β-dibromoenal into α,β-unsaturated esters or amides with high stereoselectivity through C-O or C-N bond formation have been demonstrated. The NHC-catalyzed processes occur under mild con

Single step green process for the preparation of substituted cinnamic esters with trans-selectivity

The invention provides a green process for direct oxidation of a large number of substituted or unsubstituted cinnamaldehydes or cinnamyl alcohols into the corresponding alkyl or aryl cinnamates in one step. The process of the present invention is a convenient and efficient green process for the preparation of various aryl or alkyl cinnamates under conventional, microwave and ultrasound directly from cinnamaldehydes or cinnamyl alcohols in the presence of an oxidizing agent, catalyst and an alcohol, with or without an organic solvent. These esters are immensely important compounds in flavor, perfumery and pharmaceutical industries. There are several prior arts available for the preparation of cinnamic esters, but all of them suffer from deficiencies such as use of expensive reagents and catalysts, harsh reaction conditions, use of toxic chemicals and others. In contrast, the present methodology is extremely simple and involves reaction of the substrate with an oxidizing agent mixed with a homogeneous or heterogeneous catalyst and an alcohol with or without organic solvent by stirring at room temperature or refluxing or under microwave or ultrasound irradiation to get the requisite products.

2,6-Dimethyl-4-nitrobenzoic anhydride (DMNBA): An effective coupling reagent for the synthesis of carboxylic esters and lactones

Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.

An efficient chemoselective strategy for the preparation of (E)-cinnamic esters from cinnamaldehydes using heterogeneous catalyst and DDQ

An efficient chemoselective protocol is developed for the synthesis of (E)-cinnamic esters from substituted cinnamaldehydes or cinnamyl alcohols using a combination of DDQ and heterogeneous catalyst under microwave irradiation. The method showed remarkable selectivity for cinnamaldehydes over aliphatic and aromatic aldehydes, which is a novel finding. The results demonstrate that the developed protocol can be a useful synthetic tool for chemoselective esterification in total synthesis of complex organic compounds.

A new method for the synthesis of carboxylic esters and lactones with di-2-thienyl carbonate (2-DTC) by the promotion of DMAP and iodine

The esterification of carboxylic acids with alcohols by using di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino) pyridine (DMAP) proceeded smoothly to afford the corresponding esters in good-to-high yields along with 2(5H)-thiophenone. This esterification was accelerated by the addition of an equimolar amount of iodine to afford the esters in higher yields within a shorter reaction time. Further, cyclization of ω-hydroxycarboxylic acids with an equimolar amount of 2-DTC in the presence of a catalytic amount of DMAP, followed by the addition of 1-4 equimolar amounts of iodine, afforded the corresponding lactones in good-to-high yields under mild conditions. This method was successfully employed in the synthesis of erythro-aleuritic acid lactone.

An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones: A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts

Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine by the promotion of a basic catalyst such as 4-(dimethylamino)pyridine. A variety of lactones are also prepared in high yields at room temperature from the corresponding ω-hydroxycarboxylic acids with use of 2-methyl-6-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. A similar reaction occurs with triethylamine when using a catalytic amount of 4-(dimethylamino)pyridine 1-oxide as an effective promoter for the intramolecular condensation reaction. These methods are successfully applied to the synthesis of erythro-aleuritic acid lactone and an eight-membered-ring lactone moiety of octalactins A and B. The efficiency of the cyclizations is compared to those of other reported lactonizations.

Efficient method for the esterification of carboxylic acids with alcohols using di-2-thienyl carbonate promoted by DMAP and iodine

Reaction of carboxylic acids with alcohols by using an equimolar amount of di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP) followed by addition of an equimolar amount of iodine proceeded smoothly to afford the corresponding esters and 2(5H)-thiophenone in good to high yields.

A new condensation reaction for the synthesis of carboxylic esters from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride

Various carboxylic esters were obtained in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine in the presence of a catalytic amount of 4-(