Methyl cinnamate

Methyl cinnamate[1][2]
Skeletal formula of methyl cinnamate
Ball-and-stick model of the methyl cinnamate molecule
Names
Preferred IUPAC name
Methyl (2E)-3-phenylprop-2-enoate
Other names
Methyl cinnamate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.813
EC Number 203-093-8
KEGG
UNII
Properties
C10H10O2
Molar mass 162.19 g·mol−1
Density 1.092 g/cm3
Melting point 34–38 °C (93–100 °F; 307–311 K)
Boiling point 261–262 °C (502–504 °F; 534–535 K)
Insoluble
Hazards
S-phrases (outdated) S22 S24/25
Flash point > 110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

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.[5]

Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.

List of plants that contain the chemical

  • Eucalyptus olida 'Strawberry
  • Ocotea quixos South American (Ecuadorian) Cinnamon, Ishpingo[6]
  • 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.[7] It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.

Compendial status

See also

References

  1. 1 2 Methyl cinnamate, at goodscents.com
  2. ↑ Methyl cinnamate, at Sigma-Aldrich
  3. ↑ 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.
  4. ↑ Boland DJ, Brophy JJ, House APN (1991). Eucalyptus Leaf Oils. ISBN 0-909605-69-6.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Richard J. Lewis (1989). Food Additives Handbook. Springer Science & Business Media. pp. 304–. ISBN 978-0-442-20508-9.
  8. ↑ Therapeutic Goods Administration (1999). "Approved Terminology for Medicines" (PDF). Retrieved 29 June 2009.
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