Methyl cinnamate (1754-62-7, 103-26-4)

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Suppliers

• Sigma-Aldrich - Methyl cinnamate
  27.50 - 834.00 USD
• Fisher Scientific - Search for Methyl cinnamate
• TCI - Methyl cinnamate
  14.00 - 74.00 USD

Most-cited Publications

• In Situ Photo-Cross-Linking of Cinnamate Functionalized Poly(methyl methacrylate-co-2-hydroxyethyl acrylate) Fibers during Electrospinning (Macromolecules, 2004)
• Polarization and tilt-angle measurements near the smectic-A-chiral-smectic-C transition of p-(n-decyloxybenzylidene)-p-amino-(2-methyl-butyl) cinnamate (DOBAMBC) (Physical Review Letters, 1986)
• Photoreaction and Molecular Reorientation in a Nanoscaled Film of Poly(methyl 4-(methacryloyloxy)cinnamate) Studied by Two-Dimensional FTIR and UV Correlation Spectroscopy (Langmuir, 2003)
• Redox-photosensitized reactions. 11. Ru(bpy)32+-photosensitized reactions of 1-benzyl-1,4-dihydronicotinamide with aryl-substituted enones, derivatives of methyl cinnamate, and substituted cinnamonitriles: electron-transfer mechanism and structure-reactivity relationships (Journal of Organic Chemistry, 1984)
• Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of ()Indatraline and ()Sertraline (Advanced Synthesis & Catalysis, 2009)
• Ethyl Anthranilate, Ethyl Cinnamate, 2,3-Dihydrocinnamate, and Methyl Anthranilate: Four Important Odorants Identified in Pinot noir Wines of Burgundy (American Journal of Enology and Viticulture, 1995)

Areas of Application

Safety

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Trends

Alternate Names

• methyl cinnamate, propenoic-3-(14)C-labeled
• methyl cinnamate, ion(1-)
• methyl cinnamate, trans-isomer
• methyl trans-cinnamate
• methyl cinnamate, cis-isomer
• methyl cinnamate, propenoic-3-(14)C-labeled, (E)-isomer
• SMILES
  COC(=O)C=CC1=CC=CC=C1
• InChIKey
  CCRCUPLGCSFEDV-UHFFFAOYSA-N

External Links

• Pubchem - Methyl cinnamate
• Wikipedia - methyl cinnamate
  Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 26% fresh weight yield in the leaf and twigs.

Synthesis

STYRENE  +  METHYL CHLOROFORMATE (Heck terminal vinyl)

Methyl glyoxylate  +  BENZYL CHLORIDE (Wittig)

2-Propenoic acid, 3-bromo-, methyl ester, (E)-  +  CHLOROBENZENE (Stille)

SCHEMBL1657281  +  dimethyl sulfide (Corey-Kim oxidation of secondary alcohols)

Reactant  +  1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (Nicolaou IBX dehydrogenation)

Synthesis of Methyl cinnamate ›

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Methyl cinnamate

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