Methyl cinnamate

From Wikipedia, the free encyclopedia
Methyl cinnamate[1][2]
IUPAC name

Methyl (E)-3-Phenylprop-2-enoate

Identifiers
CAS number 1754-62-7 YesY
PubChem 637520
EC number 203-093-8
ChEMBL CHEMBL55060 N
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water Insoluble
Hazards
S-phrases S22 S24/25
Flash point > 110 °C (230 °F)
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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] 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 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)
  • Stanhopea embreei, an orchid
  • Vanilla

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

  • Food Chemicals Codex[7]

See also

References

  1. ↑ 1.0 1.1 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. 
  7. ↑ Therapeutic Goods Administration (1999). "Approved Terminology for Medicines". Retrieved 29 June 2009. 

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.