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Updating {{chembox}} (changes to watched fields - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipe
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{{chembox
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 395933124
| verifiedrevid = 423505240
|Reference=<ref name=goodscent>[http://www.thegoodscentscompany.com/data/rw1417571.html Methyl cinnamate], at goodscents.com</ref><ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/173282 Methyl cinnamate], at Sigma-Aldrich</ref>
| Reference = <ref name=goodscent>[http://www.thegoodscentscompany.com/data/rw1417571.html Methyl cinnamate], at goodscents.com</ref><ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/173282 Methyl cinnamate], at Sigma-Aldrich</ref>
| ImageFile = Methyl cinnamate.png
| ImageFile = Methyl cinnamate.png
| ImageSize = 190px
| ImageSize = 190px
| ImageName = Skeletal formula
| ImageAlt = Skeletal formula of methyl cinnamate
| ImageFile1 = Methyl-cinnamate-3D-balls.png
| ImageFile1 = Methyl cinnamate 3D spacefill.png
| ImageName1 = Ball-and-stick model
| ImageAlt1 = Ball-and-stick model of the methyl cinnamate molecule
| IUPACName = Methyl (''E'')-3-Phenylprop-2-enoate
| PIN = Methyl (2''E'')-3-phenylprop-2-enoate
| OtherNames =
| OtherNames = Methyl cinnamate
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=1754-62-7
| CASNo = 103-26-4
| PubChem=637520
| ChEBI = 6857
| EINECS=203-093-8
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| SMILES=COC(=O)C=CC1=CC=CC=C1
| ChEMBL = 55060
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|Section2= {{Chembox Properties
| ChemSpiderID = 21105944
| Formula=C<sub>10</sub>H<sub>10</sub>O<sub>2</sub>
| EINECS = 203-093-8
| MolarMass=162.185 g/mol
| KEGG_Ref = {{keggcite|correct|kegg}}
| Appearance=
| KEGG = C06358
| Density=1.092 g/cm^3
| PubChem = 637520
| MeltingPt=34-38 °C
| UNII_Ref = {{fdacite|correct|FDA}}
| BoilingPt=261-262 °C
| UNII = 533CV2ZCQL
| Solubility=Insoluble
| InChI = 1/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
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| InChIKey = CCRCUPLGCSFEDV-BQYQJAHWBN
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| StdInChI = 1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
| FlashPt= >230 °F
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
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| StdInChIKey = CCRCUPLGCSFEDV-BQYQJAHWSA-N
| SPhrases={{S22}} {{S24/25}}
| SMILES = COC(=O)C=CC1=CC=CC=C1
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}}
|Section2={{Chembox Properties
| C=10|H=10|O=2
| Appearance =
| Density = 1.092{{nbsp}}g/cm<sup>3</sup>
| MeltingPtC = 34–38
| BoilingPtC = 261–262
| Solubility = Insoluble
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|Section3={{Chembox Hazards
| MainHazards =
| FlashPt = >
| FlashPtC = 110
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| GHSPictograms = {{GHS07}}
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'''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]].<ref>{{cite journal | doi = 10.1590/S0103-50532003000500008 | title = Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia | year = 2003 | last1 = Viña | first1 = Amparo | last2 = Murillo | first2 = Elizabeth | journal = Journal of the Brazilian Chemical Society | volume = 14 | issue = 5 | pages = 744–9 | doi-access = free }}</ref> ''[[Eucalyptus olida]]'' has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs.<ref>{{Cite book | vauthors = Boland DJ, Brophy JJ,((House APN)) | title = Eucalyptus Leaf Oils | year = 1991 | isbn = 978-0-909605-69-8}}</ref>


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.<ref name=goodscent/>


It is known to attract males of various [[Euglossini|orchid bee]]s, such as ''[[Aglae caerulea]]''.<ref>{{cite journal | doi = 10.2307/1541248 | last1 = Williams | first1 = N.H. | last2 = Whitten | first2 = W.M. | year = 1983 | title = Orchid floral fragrances and male euglossine bees: methods and advances in the last sesquidecade | journal = Biol. Bull. | volume = 164 | issue = 3| pages = 355–395 | jstor = 1541248 | url = https://www.biodiversitylibrary.org/part/35261 }}</ref>
'''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]].<ref>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</ref><ref name=lookchem/> ''[[Eucalyptus olida]]'' has the highest known concentrations of methyl cinnamate (98%) with a 2-6% fresh weight yield in the leaf and twigs.<ref>Boland, D.J., Brophy, J.J., and A.P.N. House, ''Eucalyptus Leaf Oils'', 1991, ISBN 0-909605-69-6</ref>


[[File:Methyl cinnamate1.JPG|thumb|left|200px|Methyl cinnamate crystals extracted using steam distillation from ''Eucalyptus olida''.]]{{clear left}}
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.<ref name=goodscent/>


It is known to attract males of various [[Euglossini|orchid bee]]s, such as ''[[Aglae caerulea]]''.<ref>{{cite journal | doi = 10.2307/1541248 | last1 = Williams | first1 = N.H. | last2 = Whitten | first2 = W.M. | year = 1983 | title = Orchid floral fragrances and male euglossine bees: methods and advances in the last sesquidecade | url = | journal = Biol. Bull. | volume = 164 | issue = 3| pages = 355–395 }}</ref>

[[File:Methyl cinnamate1.JPG|thumb|left|200px|Methyl cinnamate crystals extracted using steam distillation from Eucalyptus olida.]]
{{clearleft}}
== List of plants that contain the chemical ==
== List of plants that contain the chemical ==
* ''[[Eucalyptus olida]]'' 'Strawberry gum'
* ''[[Eucalyptus olida]]'' 'Strawberry Gum'
* ''[[Ocotea quixos]]'' South American (Ecuadorian) Cinnamon, Ishpingo<ref>{{cite journal |doi=10.1016/j.foodchem.2003.07.019 |title=Chemical composition and biological activities of Ishpingo essential oil, a traditional Ecuadorian spice from Ocotea quixos (Lam.) Kosterm. (Lauraceae) flower calices |journal=Food Chemistry |volume=85 |issue=3 |pages=415–21 |year=2004 |last1=Bruni |first1=Renato |last2=Medici |first2=Alessandro |last3=Andreotti |first3=Elisa |last4=Fantin |first4=Carlo |last5=Muzzoli |first5=Mariavittoria |last6=Dehesa |first6=Marco |last7=Romagnoli |first7=Carlo |last8=Sacchetti |first8=Gianni |hdl=11381/1449234 |hdl-access=free }}</ref>
* ''[[Ocimum americanum]]'' cv.Purple Lovingly (Querendona Morada)
* ''[[Ocimum americanum]]'' cv. Purple Lovingly (Querendona Morada)
* ''Ocimum americanum'' cv. Purple Castle (Castilla Morada)
* ''Ocimum americanum'' cv. Purple Castle (Castilla Morada)
* ''Ocimum americanum'' cv. Purple Long-legged (Zancona morada)
* ''Ocimum americanum'' cv. Purple Long-legged (Zancona morada)
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* ''[[Ocimum basilicum]]'' cv. Sweet Castle (Dulce de Castilla)
* ''[[Ocimum basilicum]]'' cv. Sweet Castle (Dulce de Castilla)
* ''Ocimum basilicum'' cv. White Compact (Blanca compacta)
* ''Ocimum basilicum'' cv. White Compact (Blanca compacta)
* ''Ocimum basilicum'' cv. large green leaves (Verde des horjas grandes)
* ''Ocimum basilicum'' cv. large green leaves ({{lang|es|verde des horjas grandes}})
* ''[[Ocimum micranthum]]'' cv. Cinnamon (Canela)
* ''[[Ocimum micranthum]]'' cv. Cinnamon (Canela)
* ''[[Ocimum minimum]]'' cv. Little Virgin (Virgen pequena)
* ''[[Ocimum minimum]]'' cv. Little Virgin (Virgen pequena)
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* ''[[Ocimum]]'' sp. cv. Purple ruffle (Crespa morada)
* ''[[Ocimum]]'' sp. cv. Purple ruffle (Crespa morada)
* ''[[Ocimum]]'' sp. cv. White Ruffle (Crespa blanca)
* ''[[Ocimum]]'' sp. cv. White Ruffle (Crespa blanca)
* ''[[Stanhopea embreei]]'', an orchid
* [[Vanilla]]


== Toxicology & safety ==
== Toxicology and safety ==
Moderately toxic by ingestion. The oral LD50 for rats is 2610&nbsp;mg/kg.<ref> ''[[Food and Cosmetics Toxicology]]''. No. 13 (1975),p681.</ref> It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.
Moderately toxic by ingestion. The oral {{LD50}} for rats is 2610&nbsp;mg/kg.<ref>{{cite book|author=Richard J. Lewis|title=Food Additives Handbook|url=https://books.google.com/books?id=nC7OGhzZn5YC&pg=PA304|year=1989|publisher=Springer Science & Business Media|isbn=978-0-442-20508-9|pages=304–}}</ref>
It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.
<ref name=lookchem>[http://www.lookchem.com/Methyl-cinnamate/ Lookchem]</ref>


==Compendial status==
==Compendial status==
* [[Food Chemicals Codex]].<ref name=ptm>{{cite web
* [[Food Chemicals Codex]]<ref name=ptm>{{cite web
| last = [[Therapeutic Goods Administration]]
| last = Therapeutic Goods Administration
| author-link = Therapeutic Goods Administration
| first =
| authorlink =
| coauthors =
| title = Approved Terminology for Medicines
| title = Approved Terminology for Medicines
| work =
| publisher =
| date = 1999
| date = 1999
| url = http://www.tga.gov.au/docs/pdf/aan/aan.pdf
| url = http://www.tga.gov.au/docs/pdf/aan/aan.pdf
| access-date = 29 June 2009
| format =
| archive-url = https://web.archive.org/web/20060522093356/http://www.tga.gov.au/docs/pdf/aan/aan.pdf
| doi =
| accessdate = 29 June 2009
| archive-date = 22 May 2006
| url-status = dead
}}</ref>
}}</ref>

==References==
<references/>


== See also ==
== See also ==
* [[Eucalyptus oil]]
* [[Eucalyptus oil]]
* [[Ralf Sieckmann v Deutsches Patent und Markenamt]], a court case concerning a company attempting to [[Non-conventional trademark|trademark the chemical compound]].

== References ==
{{Reflist}}


{{DEFAULTSORT:Methyl Cinnamate}}
{{DEFAULTSORT:Methyl Cinnamate}}
[[Category:Carboxylate esters]]
[[Category:Cinnamate esters]]
[[Category:Methyl esters]]
[[Category:Methyl esters]]
[[Category:Flavors]]
[[Category:Flavors]]
[[Category:Sweet-smelling chemicals]]


[[ja:ケイ皮酸メチル]]
[[de:Zimtsäuremethylester]]

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