Methyl cinnamate

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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+ â˜’N
    Key: CCRCUPLGCSFEDV-BQYQJAHWSA-N â˜’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 Â°C (93–100 Â°F; 307–311 K)
Boiling point 261–262 Â°C (502–504 Â°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 Â°C (230 Â°F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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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'
  • Ocotea quixos South American (Ecuadorian) Cinnamon, Ishpingo[7]
  • 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.[8] It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.

Compendial status

See also

References

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