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Methyl cinnamate is the
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
of
cinnamic acid Cinnamic acid is an organic compound with the formula phenyl, C6H5-CH=CH-Carboxylic acid, COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxy ...
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 The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown Hybrid (biology), hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit ...
, and some culinary spices, such as
Sichuan pepper Sichuan pepper (, also known as Sichuanese pepper, Szechuan pepper, Chinese prickly ash, Chinese pepper, Mountain pepper, and ''mala'' pepper, is a spice commonly used in Sichuan cuisine in China, Bhutan and in northeast India. It is called mej ...
and some varieties of
basil Basil (, ; , ; ''Ocimum basilicum'' (, )), also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a hardiness (plants), tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" r ...
. '' Eucalyptus olida'' has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs. 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. It is known to attract males of various
orchid bee The tribe Euglossini, in the subfamily Apinae, commonly known as orchid bees or euglossine bees, are the only group of corbiculate bees whose non-parasitic members do not all possess eusocial behavior. Description, distribution, and behavior ...
s, such as '' Aglae caerulea''.


List of plants that contain the chemical

* '' Eucalyptus olida'' 'Strawberry Gum' * '' Ocotea quixos'' South American (Ecuadorian) Cinnamon, Ishpingo * '' 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 Basil (, ; , ; ''Ocimum basilicum'' (, )), also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a hardiness (plants), tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" r ...
'' cv. Sweet Castle (Dulce de Castilla) * ''Ocimum basilicum'' cv. White Compact (Blanca compacta) * ''Ocimum basilicum'' cv. large green leaves () * '' Ocimum micranthum'' cv. Cinnamon (Canela) * '' Ocimum minimum'' cv. Little Virgin (Virgen pequena) * ''Ocimum minimum'' cv. Purple Virgin (Virgen morada) * ''
Ocimum ''Ocimum'' is a genus of aromatic annual and perennial herbs and shrubs in the family Lamiaceae, native to the tropical and warm temperate regions of all 6 inhabited continents, with the greatest number of species in Africa. Its best known spe ...
'' sp. cv. Purple ruffle (Crespa morada) * ''
Ocimum ''Ocimum'' is a genus of aromatic annual and perennial herbs and shrubs in the family Lamiaceae, native to the tropical and warm temperate regions of all 6 inhabited continents, with the greatest number of species in Africa. Its best known spe ...
'' sp. cv. White Ruffle (Crespa blanca) * '' Stanhopea embreei'', an orchid *
Vanilla Vanilla is a spice derived from orchids of the genus ''Vanilla (genus), Vanilla'', primarily obtained from pods of the flat-leaved vanilla (''Vanilla planifolia, V. planifolia''). ''Vanilla'' is not Autogamy, autogamous, so pollination ...


Toxicology and safety

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


Compendial status

*
Food Chemicals Codex The Food Chemicals Codex (FCC) is a collection of internationally recognized standards for the purity and identity of food ingredients. Scope The FCC features more than 1,250 monographs, including food-grade chemicals, processing aids, foods (suc ...


See also

*
Eucalyptus oil Eucalyptus oil is the generic name for distilled oil from the leaves of ''Eucalyptus'', a genus of the plant family Myrtaceae, mostly native to Australia but cultivated worldwide. Eucalyptus oil has a history of wide application, as a pharmace ...
* Ralf Sieckmann v Deutsches Patent und Markenamt, a court case concerning a company attempting to trademark the chemical compound.


References

{{DEFAULTSORT:Methyl Cinnamate Cinnamate esters Methyl esters Flavors Sweet-smelling chemicals ja:ケイ皮酸メチル