Methyl cinnamate

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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 3D model Interactive image
KEGG C06358 N
PubChem 637520
  • 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 162.19 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
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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]

File:Methyl cinnamate1.JPG
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

See also

References

  1. ↑ 1.0 1.1 Methyl cinnamate, at goodscents.com
  2. ↑ Methyl cinnamate, at Sigma-Aldrich
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.

ja:ケイ皮酸メチル

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