103-53-7

Basic information

• Product Name: Phenethyl cinnamate
• Synonyms: B-PHENYLETHYL CINNAMATE;Benzylcarbinyl 3-phenyl propenoate;benzylcarbinyl cinnamate;BETA PHENYL ETHYL CINNAMATE;FEMA 2863;2-Phenylethyl 3-phenyl propenoate;2-phenylethyl cinnamate;PHENYLETHYL CINNAMATE
• CAS NO: 103-53-7
• Molecular Formula: C₁₇H₁₆O₂
• Molecular Weight: 252.31
• EINECS: 203-120-3
• Product Categories: Cinnamic acid
• Mol File: 103-53-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 355.49°C (rough estimate)
• Flash Point: >230 °F
• Appearance: White crystals or amorphous powder
• Density: 1.0832 (rough estimate)
• Vapor Pressure: 8.49E-07mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: 523μg/L at 20℃
• CAS DataBase Reference: Phenethyl cinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenethyl cinnamate(103-53-7)
• EPA Substance Registry System: Phenethyl cinnamate(103-53-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: GE0405000
• Hazardous Substances Data: 103-53-7(Hazardous Substances Data)

Usage

Description

Phenethyl cinnamate is a crystalline solid with a melting point of 65-68°C, characterized by a heavy, rosy, balsamic odor. It is known for its sweet, balsamic scent reminiscent of rose and, at low levels, has a sweet, plum-like taste.

Uses

Used in Fragrance Industry:
Phenethyl cinnamate is used as a fixative in blossom fragrances for its ability to enhance and prolong the scent of various fragrances.
Used in Flavor Industry:
Phenethyl cinnamate is used as a flavoring agent for its sweet, plum-like taste, adding a unique and pleasant flavor to various food and beverage products.

Preparation

From phenylethyl alcohol and methylcinnamate by alcohol interchange esterification.

Flammability and Explosibility

Nonflammable

Safety Profile

Mildly toxic by ingestion. A skinirritant. When heated to decompositionit emits acrid smoke and irritating fumes.

InChI:InChI=1/C17H16O2/c18-17(12-11-15-7-3-1-4-8-15)19-14-13-16-9-5-2-6-10-16/h1-12H,13-14H2/b12-11+

Upstream product

• 60-12-8 2-phenylethanol 
• 73789-34-1 cinnamic acid 4-chlorophenyl ester 
• 621-79-4 cinnamamide 
• 140-10-3 (E)-3-phenylacrylic acid 
• 621-82-9 Cinnamic acid 
• 103-63-9 1-phenyl-2-bromoethane 
• 102-92-1 Cinnamoyl chloride 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 104-62-1 formic acid phenethyl ester 
• 2757-04-2 phenyl cinnamate 
• 153874-59-0 methyl 2-phenylethyl 2-(phenylmethylidene)propanedioate 
• 153874-58-9 methyl 2-phenylethyl propanedioate 

Downstream Products

• 28049-10-7 3-phenylpropionic acid 2-phenylethyl ester 

Relevant articles and documents

A rapid and practical catalytic esterification for the preparation of caffeic acid esters

A convenient and practical catalytic method for the preparation of caffeic acid esters is reported. This esterification was carried out with high efficiency in the presence of ytterbium triflate in nitromethane without any other auxiliary reagents. The wide scope of application and especially the higher reactivity and more convenient procedure than previous methods make it a valuable application for the synthesis of caffeic acid esters and other cinnamic acid esters.

Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles

We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.

Caffeic acid phenethyl ester (CAPE)-derivatives act as selective inhibitors of acetylcholinesterase

Unexpected inhibitory effects against eeAChE could be found for a newly synthesized class of caffeic acid phenethyl ester (CAPE)derivatives. Thus, phenethyl-(E)-3-(3,5-dimethoxy-4-phenethoxyphenyl)-acrylate (Ki = 1.97 ± 0.38 μM, Ki′ = 2.44 ± 0.07 μM)and 4-(2-(((E)-3-(3,4-bis(benzyloxy)phenyl)acryloyl)oxy)ethyl)-1,2-phenylene (2E,2′E)-bis(3-(3,4-bis(benzyloxy)phenyl)acrylate)(Ki = 0.72 ± 0.31 μM, Ki′ = 1.80 ± 0.21 μM)showed very good inhibition of eeAChE, while being non cytotoxic for malignant human cancer cells and non-malignant mouse fibroblasts. Also, they are weak inhibitors for BChE (from equine serum).