Methyl cinnamate

Methyl cinnamate[1][2]
Skeletal formula of methyl cinnamate
Ball-and-stick model of the methyl cinnamate molecule
Names
IUPAC name
Methyl (E)-3-Phenylprop-2-enoate
Identifiers
103-26-4 N
ChEMBL ChEMBL55060 N
ChemSpider 21105944 N
EC Number 203-093-8
Jmol interactive 3D Image
KEGG C06358 N
PubChem 637520
Properties
C10H10O2
Molar mass 162.19 g·mol−1
Density 1.092 g/cm3
Melting point 34 to 38 °C (93 to 100 °F; 307 to 311 K)
Boiling point 261 to 262 °C (502 to 504 °F; 534 to 535 K)
Insoluble
Hazards
S-phrases 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

Toxicology and safety

Moderately toxic by ingestion. The oral LD50 for rats is 2610 mg/kg.[6] 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. doi:10.1590/S0103-50532003000500008.
  4. Boland, D.J., Brophy, J.J., and A.P.N. House (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. Food and Cosmetics Toxicology (13): 681. 1975. Missing or empty |title= (help)
  7. Therapeutic Goods Administration (1999). "Approved Terminology for Medicines" (PDF). Retrieved 29 June 2009.
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