Methyl cinnamate

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+ ☒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 162.188 g·mol−1
Density 1.092 g/cm3
Melting point 34–38 °C (93–100 °F; 307–311 K)
Boiling point 261–262 °C (502–504 °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 °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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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]

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.
  1. ^ a b Methyl cinnamate, at goodscents.com
  2. ^ Methyl cinnamate, at Sigma-Aldrich
  3. ^ "Methyl cinnamate". pubchem.ncbi.nlm.nih.gov.
  4. ^ 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): 744–9. doi:10.1590/S0103-50532003000500008.
  5. ^ Boland DJ, Brophy JJ, House APN (1991). Eucalyptus Leaf Oils. ISBN 978-0-909605-69-8.
  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. JSTOR 1541248.