122-69-0

Basic information

• Product Name: Cinnamyl cinnamate
• Synonyms: 3-Phenyl-2-propen-1-yl 3-phenyl propenoate;3-PHENYLALLYL CINNAMATE;3-PHENYL-2-PROPENYL CINNAMATE;(E)-3-PHENYL-ACRYLIC ACID (E)-3-PHENYL-ALLYL ESTER;CINNAMYL CINNAMATE;CINNAMIC ACID CINNAMYL ESTER;FEMA 2298;(2E)-3-Phenyl-2-propenyl (2E)-3-phenyl-2-propenoate
• CAS NO: 122-69-0
• Molecular Formula: C₁₈H₁₆O₂
• Molecular Weight: 264.32
• EINECS: 204-566-1
• Product Categories: Cinnamic acid;Alphabetical Listings;C-D;Flavors and Fragrances
• Mol File: 122-69-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: 42-45 °C(lit.)
• Boiling Point: 370 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless or with yellow liquid
• Density: 1.10
• Vapor Pressure: 8.09E-08mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Merck: 14,2304
• CAS DataBase Reference: Cinnamyl cinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: Cinnamyl cinnamate(122-69-0)
• EPA Substance Registry System: Cinnamyl cinnamate(122-69-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: GD8562000
• Hazardous Substances Data: 122-69-0(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 122-69-0 differently. You can refer to the following data:
1. Rectangular, prismic crystals.Soluble in alcohol, ether, benzene.
2. Cinnamyl cinnamate has a characteristic, faintly sweet, resinous odor.

Occurrence

Cinnamyl cinnamate is one of the most important constituents of storax: Liqidambar orientale, Liquidambar styracifluum L. It is also found in white Peru and Honduras balsams.

Uses

Perfumery, flavoring.

Preparation

From cinnamic aldehyde plus aluminium ethylate in ether or by any other suitable means. It must not contain any free cinnamic aldehyde.

Aroma threshold values

Aroma characteristics at 1%: mild, floral, balsamic, sweet, floral, jasmine and rose, with a cinnamon spicy nuance.

Taste threshold values

Taste characteristics at 10 to 25 ppm: spicy, cinnamic balsamic, with a floral, yeasty note and a lingering spicy aftertaste.

General Description

Cinnamyl cinnamate can be used as a flavoring agent and a fragrance ingredient.

Biochem/physiol Actions

Taste at 10 to 25 ppm

Synthesis

It can be extracted from storax; synthetically, by prolonged reaction of aluminum ethylate with cinnamic aldehyde in absolute ether.

InChI:InChI=1/C18H16O2/c19-18(14-13-17-10-5-2-6-11-17)20-15-7-12-16-8-3-1-4-9-16/h1-14H,15H2/b12-7+,14-13+

Upstream product

• 140-10-3 (E)-3-phenylacrylic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 2327-99-3 1-phenylpropadiene 
• 14371-10-9 (E)-3-phenylpropenal 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 104-54-1 3-Phenylpropenol 
• 103-26-4 methyl cinnamate 
• 104-55-2 3-phenyl-propenal 
• 104-53-0 3-phenyl-propionaldehyde 
• 64-17-5 ethanol 
• 29584-68-7 propynoic acid cinnamyl ester 
• 98-80-6 phenylboronic acid 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 673-32-5 1-Phenylprop-1-yne 

Downstream Products

• 100-52-7 benzaldehyde 
• 60045-27-4 3-phenylpropionic acid 3-phenylpropyl ester 
• 873-66-5 1-propenylbenzene 
• 40918-94-3 trans-Cinnamyl-2.3-diphenyl-5-oxo-cyclopentan-1-carboxylat 
• 104-54-1 3-Phenylpropenol 
• 101735-67-5 (+/-)-trans-cinnamic acid-(3-chloro-2-hydroxyimino-3-phenyl-propyl ester) 

Relevant articles and documents

Palladium-Catalyzed Hydrocarboxylation of Allenes

-

Visible Light-Mediated Synthesis of Enantiopure g-Cyclobutane Amino and 3-(Aminomethyl)-5-phenylpentanoic Acids

A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.

Preparation method of cinnamyl cinnamate

The invention relates to a preparation method of cinnamyl cinnamate. In an oil bath, methyl cinanmate, cinnamyl alcohol and potassium carbonate are mixed and heated under stirring, and low boiling substances are distilled off while reacting, heating is stopped to cool, water and ethyl acetate are added for washing until the water phase is neutral, and the oil phase is subjected to reduced pressuredistillation after being heated to recover ethyl acetate so as to obtain cinnamyl cinnamate crude products, and the cinnamyl cinnamate crude products are recrystallized from ethanol to obtain white solid cinnamyl cinnamate. The preparation method has the advantages of simple process, short cycle, high yield, simple post-treatment, green environmental protection and the like. The cinnamyl cinnamate prepared according to the method has the advantages of pure aroma, good color, high purity and the like.