Methyl cinnamate

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Methyl cinnamate[1][2]
Skeletal formula
Ball-and-stick model
Identifiers
CAS number1754-62-7 YesY
PubChem637520
EC number203-093-8
ChEMBLCHEMBL55060 N
Jmol-3D imagesImage 1
Properties
Molecular formulaC10H10O2
Molar mass162.19 g mol−1
Density1.092 g/cm3
Melting point34 to 38 °C (93 to 100 °F; 307 to 311 K)
Boiling point261 to 262 °C (502 to 504 °F; 534 to 535 K)
Solubility in waterInsoluble
Hazards
S-phrasesS22 S24/25
Flash point> 110 °C (230 °F)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
 
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Methyl cinnamate[1][2]
Skeletal formula
Ball-and-stick model
Identifiers
CAS number1754-62-7 YesY
PubChem637520
EC number203-093-8
ChEMBLCHEMBL55060 N
Jmol-3D imagesImage 1
Properties
Molecular formulaC10H10O2
Molar mass162.19 g mol−1
Density1.092 g/cm3
Melting point34 to 38 °C (93 to 100 °F; 307 to 311 K)
Boiling point261 to 262 °C (502 to 504 °F; 534 to 535 K)
Solubility in waterInsoluble
Hazards
S-phrasesS22 S24/25
Flash point> 110 °C (230 °F)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

Toxicology and safety[edit]

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[edit]

See also[edit]

References[edit]

  1. ^ a b 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.