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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.813 Edit this at Wikidata
EC Number
  • 203-093-8
KEGG
UNII
  • InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+ ☒N
    Key: CCRCUPLGCSFEDV-BQYQJAHWSA-N ☒N
  • InChI=1/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
    Key: CCRCUPLGCSFEDV-BQYQJAHWBN
  • COC(=O)C=CC1=CC=CC=C1
Properties
C10H10O2
Molar mass 162.188 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
GHS labelling:[3]
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
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).
☒N verify (what is checkY☒N ?)

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

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

See also

References

  1. ^ a b 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.
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