Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester

Base Information

• Chemical Name: Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester
• CAS No.: 103-59-3
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• Hs Code.: 2915900090
• DSSTox Substance ID: DTXSID6047608
• ChEMBL ID: CHEMBL3183375
• Mol file: 103-59-3.mol

Synonyms:Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester;cinnamylisobutyrat-;DTXSID6047608;isobutyric acid cinnamyl ester;CHEMBL3183375;3-phenylallyl 2-methylpropanoate;AKOS028108457;FT-0623843;D95780

Chemical Property of Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester

Chemical Property:

• Appearance/Colour: Colourless to yellowish liquid, sweet, balsamic fruity odour
• Vapor Pressure: 0.000741mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Boiling Point: 307.082 °C at 760 mmHg
• Flash Point: 127.821 °C
• PSA: 26.30000
• Density: 1.02 g/cm³
• LogP: 2.89900
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 204.115029749
• Heavy Atom Count: 15
• Complexity: 213

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cinnamyl isobutyrate ≥97%, FCC, FG ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(=O)OCC=CC1=CC=CC=C1
• Uses: 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). Cinnamyl Isobutyrate is a synthetic flavoring agent that is a moderately stable, colorless to light yellow liquid of dry fruity color. it is stored in glass or tin containers. it is used to give a lift to jasmine with applications in baked goods and candy at 8 ppm.

Technology Process of Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester

There total 4 articles about Propanoic acid, 2-methyl-, 3-phenyl-2-propenyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 26.0%

cinnamyl 2-bromo-2-methylpropanoate (60533-00-8) → C26H30O4 + cinnamyl isobutyrate (103-59-3)

Guidance literature:

With indium(III) chloride; indium; In acetonitrile; Inert atmosphere; Sonication;

DOI:10.1016/j.tet.2011.03.079

Reference yield:

3-Phenylpropenol (104-54-1) + Ethyl isobutyrate (97-62-1) → cinnamyl isobutyrate (103-59-3)

Guidance literature:

With recombinant acyltransferase from Mycobacterium smegmatis; In aq. phosphate buffer; at 25 ℃; for 24h; pH=8; Green chemistry; Enzymatic reaction;

DOI:10.1021/acs.jafc.9b01790

Reference yield:

3-Phenylpropenol (104-54-1) → C26H30O4 + cinnamyl isobutyrate (103-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; dmap / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2: indium(III) chloride; indium / acetonitrile / Inert atmosphere; Sonication

With pyridine; dmap; indium(III) chloride; indium; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2011.03.079

upstream raw materials:

3-Phenylpropenol

isobutyryl chloride

cinnamyl 2-bromo-2-methylpropanoate

Ethyl isobutyrate

Downstream raw materials:

2,2-dimethyl-3-phenylpent-3-enoic acid

2,2-dimethyl-3-phenyl-pent-4-enoic acid

Refernces

• 1、 Ishihara, Jun,Watanabe, Yuki,Koyama, Noriko,Nishino, Yukihiro,Takahashi, Keisuke,Hatakeyama, Susumi. "Indium-mediated Reformatsky-Claisen rearrangement". scheme or table. p. 3659 - 3667. Retrieved 2011/06/21.