103-59-3

Basic information

• Product Name: CINNAMYL ISOBUTYRATE
• Synonyms: 2-methyl-propanoicacid,3-phenyl-2-propenylester;isobutyricacid,cinnamylester;Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester;Propanoicacid,2-methyl-,3-phenyl-2-propenylester;CINNAMYL 2-METHYLPROPANOATE;CINNAMYL-2-METHYLPROPIONATE;CINNAMYL ISOBUTYRATE;FEMA 2297
• CAS NO: 103-59-3
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26
• EINECS: 203-126-6
• Product Categories: Alphabetical Listings;C-D;Flavors and Fragrances
• Mol File: 103-59-3.mol

Chemical Properties

• Boiling Point: 254 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.008 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000741mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• CAS DataBase Reference: CINNAMYL ISOBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: CINNAMYL ISOBUTYRATE(103-59-3)
• EPA Substance Registry System: CINNAMYL ISOBUTYRATE(103-59-3)

Safety Data

• WGK Germany: 2
• RTECS: NQ4558000
• Hazardous Substances Data: 103-59-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Cinnamyl isobutyrate is used as a flavoring agent to give a lift to jasmine, providing a sweet, fruity taste and aroma. It is commonly used in baked goods and candy at a concentration of 8 ppm.
Used in Analytical Chemistry:
Cinnamyl isobutyrate may be used as an analytical reference standard for the quantification of the analyte in watermelon (EG) flavored hookah tobacco and leaf oil of Heteropyxis dehniae Suess, using gas chromatography coupled to mass spectrometry (GC-MS).
Used in Cosmetics and Personal Care Products:
Cinnamyl isobutyrate is widely used in fragrances for shampoos, decorative cosmetics, fine fragrances, toilet soaps, and other toiletries, as well as in non-cosmetic products such as household cleaners and detergents.

Preparation

By esterification of cinnamic alcohol with isobutyric acid.

InChI:InChI=1/C13H16O2/c1-11(2)13(14)15-10-6-9-12-7-4-3-5-8-12/h3-9,11H,10H2,1-2H3/b9-6+

Upstream product

• 104-54-1 3-Phenylpropenol 
• 79-30-1 isobutyryl chloride 
• 60533-00-8 cinnamyl 2-bromo-2-methylpropanoate 
• 97-62-1 Ethyl isobutyrate 

Downstream Products

• 60533-01-9 2,2-dimethyl-3-phenyl-pent-4-enoic acid 
• 60532-99-2 2,2-dimethyl-3-phenylpent-3-enoic acid 

Relevant articles and documents

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.

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.