103-56-0

Basic information

• Product Name: Cinnamyl propionate
• Synonyms: propionicacid,cinnamylester;TRANS-CINNAMYL PROPIONATE;3-PHENYL-2-PROPEN-1-YL PROPANOATE;3-PHENYL-2-PROPEN-1-YL PROPIONATE;3-PHENYLALLYL PROPIONATE;3-Phenyl-2-propenyl propanoate;CINNAMYL PROPIONATE;FEMA 2301
• CAS NO: 103-56-0
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 203-124-5
• Mol File: 103-56-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 289 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.032 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00136mmHg at 25°C
• Refractive Index: n20/D 1.535(lit.)
• Water Solubility: 69mg/L at 25℃
• CAS DataBase Reference: Cinnamyl propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Cinnamyl propionate(103-56-0)
• EPA Substance Registry System: Cinnamyl propionate(103-56-0)

Safety Data

• Statements: 36/37/38-38-22
• Safety Statements: 26-37-45-44
• WGK Germany: 2
• RTECS: GE2360000
• TSCA: Yes
• Hazardous Substances Data: 103-56-0(Hazardous Substances Data)

Usage

Description

Cinnamyl propionate is an organic compound with a spicy, fruity odor and a woody, balsamic undertone. It has a sweet, warm, powerful, and spicy taste. It has not been reported to occur naturally and is characterized by its taste threshold values and taste characteristics at 10 ppm, which include sweet, floral, waxy, balsamic, green, punch, grape, and cherry notes.

Uses

Used in Flavor and Fragrance Industry:
Cinnamyl propionate is used as a flavoring agent for its sweet, floral, waxy, balsamic, green, punch, grape, and cherry taste characteristics. Its unique taste profile makes it suitable for enhancing the flavor of various food and beverage products.
Used in Perfumery:
Cinnamyl propionate is used as a fragrance ingredient due to its spicy, fruity odor with a woody, balsamic undertone. It can be incorporated into perfumes and other scented products to provide a warm, spicy, and complex aroma.
Used in Cosmetics:
In the cosmetics industry, cinnamyl propionate can be used as a scent additive to provide a pleasant and long-lasting fragrance to various cosmetic products, such as lotions, creams, and body care products.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, cinnamyl propionate could potentially be used in the pharmaceutical industry as a flavoring agent for medicinal products to improve their taste and palatability, making them more acceptable for patients.

Preparation

By direct esterification of cinnamic alcohol with propionic acid under azeotropic conditions, or with propionic anhydride (Arctander, 1969).

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

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

Upstream product

• 104-54-1 3-Phenylpropenol 
• 79-03-8 propionyl chloride 
• 105-37-3 Ethyl propionate 
• 40630-85-1 cinnamyl 2-bromopropanoate 
• 802294-64-0 propionic acid 
• 591-50-4 iodobenzene 
• 2408-20-0 prop-2-enyl propanoate 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 256663-37-3 2-methyl-3-phenyl-pent-4-enoic acid 
• 80896-22-6 3-benzylamino-3-phenyl-1-propanol 
• 232602-14-1 1-(2-benzyl-pyridin-3-yl)-ethanone 
• 1336877-38-3 2-benzylbenzo[h]quinoline 
• 16573-51-6 6-benzyl-phenanthridine 
• 1745-77-3 2-benzylquinoline 
• 75961-62-5 2-benzyl-4-(carbomethoxy)pyridine 
• 30046-68-5 2-benzyl-4,6-dimethylpyridine 
• 10131-46-1 2-benzyl-6-methylpyridine 
• 5191-54-8 2-benzyl-4-methyl pyridine 
• 101-82-6 2-Benzylpyridine 

Relevant articles and documents

Palladium-Catalyzed Three-Component Coupling Reaction of Allyl Carboxylates, Norbornenes and Diboronates Involving Sequential Olefins Insertion and Borylation Reaction

An efficient Pd-catalyzed three-component coupling reaction of allyl carboxylates, norbornenes and diboronates is described, which allows efficient assembly of C(sp3)—C(sp3) and C(sp3)—B bonds in a single process. Moreover, this approach shows advantages of good chemo- and regioselectivity, as well as good substrates suitability.

Cinnamyl alcohol fatty acid ester derivative and application and preparation method thereof

The invention relates to a derivative and an application and a preparation method thereof, in particular to a cinnamyl alcohol fatty acid ester derivative and an application and a preparation method thereof. As application of a percutaneous absorption penetration enhancer, a percutaneous administration preparation is prepared, so that the percutaneous absorption of a drug is improved, and the cumulative penetration amount of the drug is increased. The cinnamyl alcohol fatty acid ester derivative is prepared into fatty acyl chloride, and the fatty acyl chloride reacts with cinnamyl alcohol to obtain the cinnamyl alcohol fatty acid ester derivative. The compound can be applied to the percutaneous administration preparation to enhance the drug permeability, can further be used as perfume to cover up the bad smell of the preparation, and has wide potential application prospects.

An examination of the scope and stereochemistry of the Ireland-Claisen rearrangement of boron ketene acetals

The Ireland-Claisen rearrangement of boron ketene acetals is described. The boron ketene acetal intermediates are formed through a soft enolization that obviates the use of strong bases and the intermediacy of alkali metal enolates. Yields and diastereoselectivities of these rearrangements are very sensitive to the choice of boron reagent, even among those that have been shown to effect quantitative formation of boron ketene acetals from esters. The rearrangement occurs at room temperature for all substrates with generally high levels of stereoselectivity. In contrast to previous reports using boron triflates, the use of a commercially available boron iodide reagent allows for a wider substrate scope that extends to propionates and arylacetates, as well as the previously described α-oxygenated esters. This work also provides insight into the dynamic nature of boron ketene acetals and the ramifications of this behavior for reactions in which they are intermediates. Borane down: Boron enolates of allylic esters are efficiently generated at -78 °C using cHx2BI (dicyclohexyliodoborane)·Et3N. These rearrange smoothly on being warmed to room temperature to give generally high diastereoselectivity in forming γ,δ-unsaturated acids (see scheme). The rearrangements provide a key insight into the dynamic nature of boron ketene acetals.