Methyl cinnamate

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^[1][2]

Names
Preferred IUPAC name Methyl (2E)-3-phenylprop-2-enoate
Other names Methyl cinnamate
Identifiers
CAS Number	103-26-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6857
ChEMBL	ChEMBL55060 Y
ChemSpider	21105944 Y
ECHA InfoCard	100.002.813
EC Number	203-093-8
KEGG	C06358 Y
PubChem CID	637520
UNII	533CV2ZCQL Y
CompTox Dashboard (EPA)	DTXSID6042151
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
SMILES COC(=O)C=CC1=CC=CC=C1
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
GHS labelling:[3]
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	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). N verify (what is YN ?) Infobox references

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

• Food Chemicals Codex^[9]

See also

• Eucalyptus oil
• Ralf Sieckmann v Deutsches Patent und Markenamt, a court case concerning a company attempting to trademark the chemical compound.