Methyl cinnamate


Methyl cinnamate
Methyl cinnamate[1][2]
Identifiers
CAS number 1754-62-7
PubChem 637520
EC number 203-093-8
Jmol-3D images Image 1
Properties
Molecular formula C10H10O2
Molar mass 162.185 g/mol
Density 1.092 g/cm^3
Melting point

34-38 °C

Boiling point

261-262 °C

Solubility in water Insoluble
Hazards
S-phrases S22 S24/25
Flash point >230 °F
 YesY cinnamate (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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][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'
  • 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)

Toxicology & 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. [4]

Compendial status

  • Food Chemicals Codex.[8]

References

  1. ^ a b Methyl cinnamate, at goodscents.com
  2. ^ Methyl cinnamate, at Sigma-Aldrich
  3. ^ Amparo Viña; Elizabeth Murillo, Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia, Journal of the Brazilian Chemical Society, vol.14 no.5 São Paulo Sept./Oct. 2003 http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500008
  4. ^ a b Lookchem
  5. ^ Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6
  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. 
  7. ^ Food and Cosmetics Toxicology. No. 13 (1975),p681.
  8. ^ Therapeutic Goods Administration (1999). "Approved Terminology for Medicines". http://www.tga.gov.au/docs/pdf/aan/aan.pdf. Retrieved 29 June 2009. 

See also



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