Description
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 2 - 6 % fresh weight yield in the leaf and twigs.
Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry.
It is known to attract males of various orchid bees, such as Aglae caerulea.
Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.
Occurrence
Reported found in the oil from rhizomes of Alpinia malaccensis, in the oil from leaves of Ocimum canum
Sims.; in the oil of Narcissus jonquilla L.; in the oil from rhizomes of Gastrochilus panduratum Ridl.; two isomers (cis- and trans-)
exist in natural. Also reported found in cranberry, guava, pineapple, strawberry fruit and jam, cinnamon leaf, Camembert cheeses,
cocoa, avocado, plum, prune, cloudberry, starfruit, plum brandy, rhubarb, beli (Aegle marmelos Correa), loquat and Bourbon vanilla.
Definition
ChEBI: Methyl cinnamate is a methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries. It has a role as a flavouring agent, a fragrance, an insect attractant, a volatile oil component and an anti-inflammatory agent. It is a methyl ester and an alkyl cinnamate.
Preparation
By esterification of cinnamic acid with methanol using HCl as catalyst, or by adding HCl to a boiling solution of cinnamyl
nitrile in methanol.
General Description
Methyl cinnamate is an important flavoring agent and fragrance ingredient. It is one of the main aroma components of basil oil, Japanese and Korean matsutake mushrooms.
Flammability and Explosibility
Nonflammable
Synthesis
Take 14.8g of cinnamic acid, 12.8g of methanol and 0.74g of supported acidic catalyst, respectively, add them to a 250ml flask, heat and reflux for 3h, and then perform vacuum distillation until no liquid is distilled out. Filter while hot to remove the solid catalyst and maintain the liquid phase temperature at 43℃. Add 6% KCO3 solution to the product until the solution pH is 8.5 while maintaining the solution temperature at 43℃, let stand and separate, remove the water phase, wash the product with twice the volume of 42℃ deionized water, let stand and separate, remove the water phase, and repeat this step until the solution pH is 7. Add three times the volume of 10℃ deionized water to the product under continuous stirring, and a light yellow solid will precipitate, methyl cinnamate, with a yield of 86%.
