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
• Article Data: 12

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

Description

3-PHENYLPROPYL CINNAMATE is an organic compound that is characterized by its sweet, heavy, floral-fruity odor with a balsamic note. It is also known for its sweet flavor that is reminiscent of cocoa. 3-PHENYLPROPYL CINNAMATE is reported to be found in various natural sources such as Oriental storax, American storax, Peru balsam from Honduras, and Sumatra benzoin.

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

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.

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

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.