Methyl cinnamate

Methyl cinnamate^[1][2]

Names
IUPAC name Methyl (E)-3-Phenylprop-2-enoate
Identifiers
CAS Registry Number	1754-62-7 Y
ChEMBL	ChEMBL55060 N
ChemSpider	21105944 N
EC number	203-093-8
InChI 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
Jmol-3D images	Image
KEGG	C06358 N
PubChem	637520
SMILES COC(=O)C=CC1=CC=CC=C1
Properties
Molecular formula	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)
Solubility in water	Insoluble
Hazards
S-phrases	S22 S24/25
Flash point	> 110 °C (230 °F; 383 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/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

• 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

• Food Chemicals Codex^[7]

See also

• Eucalyptus oil

References

1. ↑ 1.0 1.1 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.  Missing or empty |title= (help)
7. ↑ Therapeutic Goods Administration (1999). "Approved Terminology for Medicines" (PDF). Retrieved 29 June 2009.