78761-38-3

Basic information

• Product Name: CINNAMYL PROPIONATE
• Synonyms: TRANS-CINNAMYL PROPIONATE;FEMA 2301;GAMMA-PHENYLALLYL PROPIONATE;3-PHENYL-2-PROPEN-1-YL PROPANOATE;3-PHENYL-2-PROPEN-1-YL PROPIONATE;TRANS-CINNAMYL PROPIONATE 97+%;[(E)-3-phenylprop-2-enyl] propanoate;(E)-cinnamyl propionate
• CAS NO: 78761-38-3
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 203-124-5
• Product Categories: Alphabetical Listings;C-D;Flavors and Fragrances
• Mol File: 78761-38-3.mol

Chemical Properties

• Boiling Point: 289 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.032 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.535(lit.)
• CAS DataBase Reference: CINNAMYL PROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: CINNAMYL PROPIONATE(78761-38-3)
• EPA Substance Registry System: CINNAMYL PROPIONATE(78761-38-3)

Safety Data

• WGK Germany: 2
• RTECS: GE2360000
• Hazardous Substances Data: 78761-38-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Cinnamyl propionate is used as a flavoring agent for its sweet, balsamic, and spicy cinnamon-like aroma. It is commonly employed in the food and beverage industry to impart a warm, spicy flavor to various products, such as baked goods, confectionery, and beverages.
Used in Perfumery:
In the perfumery industry, cinnamyl propionate is used as a fixative agent to enhance the longevity and stability of fragrances. Its sweet, spicy, and balsamic notes contribute to the overall complexity and depth of perfume compositions.
Used in Aromatherapy:
Cinnamyl propionate is also utilized in aromatherapy for its potential therapeutic benefits. Its warm, spicy scent is believed to promote relaxation, reduce stress, and improve mood. It can be used in diffusers, candles, or massage oils to create a calming and soothing atmosphere.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, cinnamyl propionate is used as a fragrance ingredient to add a pleasant, spicy scent to products such as soaps, lotions, and creams. Its natural origin and appealing aroma make it a popular choice for creating unique and attractive product scents.
Used in Pharmaceutical Industry:
Cinnamyl propionate may also find applications in the pharmaceutical industry as a flavoring agent for medications, particularly those with an unpleasant taste. Its sweet, cinnamon-like flavor can help mask the taste of certain active pharmaceutical ingredients, making them more palatable for patients.
Overall, cinnamyl propionate is a versatile compound with a wide range of applications across various industries, primarily due to its unique and appealing cinnamon-like aroma and flavor. Its natural origin and potential therapeutic properties make it a valuable ingredient in the development of consumer products.

Upstream product

• 40630-85-1 cinnamyl 2-bromopropanoate 
• 104-54-1 3-Phenylpropenol 
• 123-62-6 propionic acid anhydride 
• 772-00-9 4-phenyl-1,3-dioxane 
• 802294-64-0 propionic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 105-38-4 vinyl propionate 
• 21040-45-9 Cinnamyl acetate 
• 99567-84-7 1-phenyl-1,3-bis-propionyloxy-propane 
• 79-03-8 propionyl chloride 
• 591-50-4 iodobenzene 
• 2408-20-0 prop-2-enyl propanoate 
• 105-37-3 Ethyl propionate 

Downstream Products

• 74120-63-1 (E)-1,4-diphenyl-1,5-hexadiene 
• 132819-86-4 ethyl 3-(α-cinnamyl)-1-tosylindole-2-carboxylate 
• 1051873-38-1 C₁₉H₂₁NO₄S 
• 80359-92-8 5-phenyl-6-hepten-3-one 
• 21040-45-9 Cinnamyl acetate 
• 802294-64-0 propionic acid 
• 87012-79-1 2-(trans-cinnamyloxy)-1-butene 
• 80896-22-6 3-benzylamino-3-phenyl-1-propanol 

Relevant articles and documents

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.

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.

Efficient Enzymatic Preparation of Flavor Esters in Water

A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.

Synthesis of α-(Pentafluorosulfanyl)- and α-(Trifluoromethyl)-Substituted Carboxylic Acid Derivatives by Ireland-Claisen Rearrangement

Earlier studies have shown that [3,3]-sigmatropic rearrangements of allyl esters are useful for the construction of fluorine-containing carboxylic acid derivatives. This paper describes the synthesis of 3-aryl-pent-4-enoic acid derivatives bearing either a pentafluorosulfanyl (SF5) or a trifluoromethyl (CF3) substituent in the 2-position by treatment of corresponding SF5- or CF3-acetates of p-substituted cinnamyl alcohols with triethylamine followed by trimethylsilyl triflate (TMSOTf). This Ireland-Claisen rearrangement delivered approximate 1:1 mixtures of syn/anti diastereoisomers due to tiny differences (3N) led to oligomerization of the cinnamyl SF5- and CF3-acetates. Treatment of the corresponding regioisomeric 1-phenyl-prop-2-en-1-yl acetates under the latter conditions resulted in [1,3]-sigmatropic rearrangement and subsequent oligomerization of the intermediately formed cinnamyl esters. When Et3N was added first followed by TMSOTf, no further reaction of the formed ester was detected.

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.

Solvent-free transesterification in a ball-mill over alumina surface

An efficient procedure for transesterification has been developed in a ball-mill in the absence of any solvent, acid/base or metal catalyst. A variety of methyl, ethyl, allyl esters have been transesterified to higher benzyl and other esters in high yields by this procedure.

Indium-mediated Reformatsky-Claisen rearrangement

A new variant of the Reformatsky-Claisen rearrangement is described. The reaction of substituted allyl α-bromoacetates with indium and indium(III) chloride under ultrasonication provides a general entry into the functionalized synthon.

5H-3-oxa-Octafluoropentanesulfonyl fluoride: a novel and efficient condensing agent for esterification, amidation and anhydridization

The use of 5H-3-oxa-octafluoropentanesulfonyl fluoride (HCF2CF2OCF2CF2SO2F) as a novel and efficient condensing reagent for esterification of carboxylic acids with alcohols and amidation of carboxylic acids with amines in the presence of 1,3-diazabicyclo[5.4.0]-undec-7-ene (DBU) is reported. HCF2CF2OCF2CF2SO2F cannot serve as a condensing agent for anhydridization of carboxylic acids, however, HCF2CF2OCF2CF2SO2F/(CH3)3SiCN system can mediate anhydridization of some aromatic carboxylic acids.

N, O-ligand accelerated zinc-catalyzed transesterification of alcohols with vinyl esters

N-Phenyldiethanolamine (1f) is an efficient ligand for zinc-catalyzed transesterification of alcohols with vinyl acetate (R3 = Me) at room temperature. In the case of using other vinyl esters (R3 = Et, n-Pr, Ph), the corresponding products were easily obtained in the presence of pyridine-type ligand 2 instead of aminoalcohol 1f.

Synthesis under reversible conditions of cyclic porphyrin dimers using palladium-catalysed allyl transesterification

Cyclic zinc-porphyrin dimers have been synthesised using reversible π-allyl palladium chemistry in the presence of bidentate pyridyl ligand templates.