Methyl cinnamate

Methyl cinnamate[1][2]
IUPAC name Methyl (E)-3-Phenylprop-2-enoate
Identifiers
CAS number	1754-62-7 Y
PubChem	637520
EC number	203-093-8
ChEMBL	CHEMBL55060 N
Jmol-3D images	Image 1
SMILES COC(=O)C=CC1=CC=CC=C1
Properties
Molecular formula	C10H10O2
Molar mass	162.185 g/mol
Density	1.092 g/cm^3
Melting point	34–38 °C
Boiling point	261–262 °C
Solubility in water	Insoluble
Hazards
S-phrases	S22 S24/25
Flash point	>230 °F
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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][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.

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)

Toxicology & safety

Moderately toxic by ingestion. The oral LD50 for rats is 2610 mg/kg.^[7] It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes. ^[4]

Compendial status

• Food Chemicals Codex.^[8]

References

1. ^ ^{a b} Methyl cinnamate, at goodscents.com
2. ^ Methyl cinnamate, at Sigma-Aldrich
3. ^ Amparo Viña; Elizabeth Murillo, Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia, Journal of the Brazilian Chemical Society, vol.14 no.5 São Paulo Sept./Oct. 2003 http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000500008
4. ^ ^{a b} Lookchem
5. ^ Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6
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. 
7. ^ Food and Cosmetics Toxicology. No. 13 (1975),p681.
8. ^ Therapeutic Goods Administration (1999). "Approved Terminology for Medicines". http://www.tga.gov.au/docs/pdf/aan/aan.pdf. Retrieved 29 June 2009. 

See also

• Eucalyptus oil