Methyl cinnamate

Chemical compound

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.^[4] Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs.^[5]

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.^[1]

It is known to attract males of various orchid bees, such as Aglae caerulea.^[6]

Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.

List of plants that contain the chemical

• Eucalyptus olida 'Strawberry Gum'
• Ocotea quixos South American (Ecuadorian) Cinnamon, Ishpingo^[7]
• Ocimum americanum cv. Purple Lovingly (Querendona Morada)
• Ocimum americanum cv. Purple Castle (Castilla Morada)
• Ocimum americanum cv. Purple Long-legged (Zancona morada)
• Ocimum americanum cv. Clove (Clavo)
• Ocimum basilicum cv. Sweet Castle (Dulce de Castilla)
• Ocimum basilicum cv. White Compact (Blanca compacta)
• Ocimum basilicum cv. large green leaves (verde des horjas grandes)
• Ocimum micranthum cv. Cinnamon (Canela)
• Ocimum minimum cv. Little Virgin (Virgen pequena)
• Ocimum minimum cv. Purple Virgin (Virgen morada)
• Ocimum sp. cv. Purple ruffle (Crespa morada)
• Ocimum sp. cv. White Ruffle (Crespa blanca)
• Stanhopea embreei, an orchid
• Vanilla

Toxicology and safety

Moderately toxic by ingestion. The oral LD50 for rats is 2610 mg/kg.^[8]It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.

Compendial status

• Food Chemicals Codex^[9]

See also

• Eucalyptus oil
• Ralf Sieckmann v Deutsches Patent und Markenamt, a court case concerning a company attempting to trademark the chemical compound.

References

1. Methyl cinnamate, at goodscents.com
2. Methyl cinnamate, at Sigma-Aldrich
3. "Methyl cinnamate". pubchem.ncbi.nlm.nih.gov.
4. Viña, Amparo; Murillo, Elizabeth (2003). "Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia". Journal of the Brazilian Chemical Society. 14 (5): 744–9. doi:10.1590/S0103-50532003000500008.
5. Boland DJ, Brophy JJ, House APN (1991). Eucalyptus Leaf Oils. ISBN 978-0-909605-69-8.
6. Williams, N.H.; Whitten, W.M. (1983). "Orchid floral fragrances and male euglossine bees: methods and advances in the last sesquidecade". Biol. Bull. 164 (3): 355–395. doi:10.2307/1541248. JSTOR 1541248.
7. Bruni, Renato; Medici, Alessandro; Andreotti, Elisa; Fantin, Carlo; Muzzoli, Mariavittoria; Dehesa, Marco; Romagnoli, Carlo; Sacchetti, Gianni (2004). "Chemical composition and biological activities of Ishpingo essential oil, a traditional Ecuadorian spice from Ocotea quixos (Lam.) Kosterm. (Lauraceae) flower calices". Food Chemistry. 85 (3): 415–21. doi:10.1016/j.foodchem.2003.07.019. hdl:11381/1449234.
8. Richard J. Lewis (1989). Food Additives Handbook. Springer Science & Business Media. pp. 304–. ISBN 978-0-442-20508-9.
9. Therapeutic Goods Administration (1999). "Approved Terminology for Medicines" (PDF). Archived from the original (PDF) on 22 May 2006. Retrieved 29 June 2009.