Methyl cinnamate

The methyl ester of cinnamic acid, also known as methyl cinnamate, is a flavoring substance listed in the EU in the Union list of flavoring substances Annex I Part A of the EC Flavouring Regulation. The molecule has a trans-substituted carbon-carbon double bond in the side chain. The isomeric cis-cinnamic acid methyl ester is referred to as "allocinnamic acid methyl ester" and is only of minor importance. Cinnamic acid methyl ester has a sweet, fruity, aromatic and balsamic smell and taste. The flavoring agent is used in a wide range of flavors (e.g. fruit, vanilla) and end products (e.g. beverages, confectionery, dairy products).

Allergologically, this cinnamic acid ester does not play a major role.

In nature, the ester is found in various plants, e.g. in musk and wild strawberries and various types of basil. The eucalyptus species Eucalyptus olida has the highest content of cinnamic acid methyl ester.

Several studies have shown that AMPA receptors (AMPA receptors are ionotropic glutamate receptors in vertebrates and consist of three major subtypes - AMPA, kainate and NMDA receptors. They mediate the majority of fast excitatory neurotransmission at chemical synapses of the central nervous system). AMPA receptors are involved in the development of neuropathic pain in the spinal cord. Animal experiments showed that metyhlcinnamate (MC) inhibited CCI-induced mechanical and thermal hypersensitivity in a dose-dependent manner. MC dose-dependently reduced CCI-induced activation of mTOR and downstream p70s6k. MC dose-dependently induced the activation of AMPK (Gui Y et al. (2018)

1. Burdock GA et al. (2010): Fenaroli's Handbook of Flavor Ingredients, Sixth Edition: CRC Press, Boca Raton; London; New York, NY, ISBN 9781420090772

2. Gui Y et al. (2018) Methyl cinnamate alleviated CCI-induced upregulation of spinal AMPA receptors and pain hypersensitivity by targeting AMPK. Eur J Pharmacol 833:183-189.

3. Nor Azah MA et al (2005): (e)-methyl cinnamate: the major component of essential oils of Alpinia malaccensis var. nobilis. Journal of Tropical Forest Science 17: 631-633
4. Regulation (EC) No 1334/2008 on flavourings and certain food ingredients with flavouring properties for use in and on foods (OJ L 354, 31.12.2008, p. 34-50).