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Methyl cinnamate: Difference between revisions

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| 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>
| ImageFile = Methyl cinnamate.svgpng
| ImageSize = 190px
| ImageAlt = Skeletal formula of methyl cinnamate
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| OtherNames = Methyl cinnamate
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changedcorrect|??}}
| CASNo = 103-26-4
| ChEBI = 6857▼
 
| UNII_RefChEMBL_Ref = {{fdaciteebicite|changedcorrect|FDAEBI}}
| UNII = 533CV2ZCQL▼
 
| PubChem = 637520▼
| EINECS = 203-093-8▼
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 55060
| ChemSpiderID_Ref = {{chemspidercite|changedcorrect|chemspider}}▼
| SMILES = COC(=O)C=CC1=CC=CC=C1▼
▲| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21105944
▲| EINECS = 203-093-8
| KEGG_Ref = {{keggcite|changedcorrect|kegg}}▼
| KEGG = C06358▼
▲| PubChem = 637520
| UNII_Ref = {{fdacite|correct|FDA}}
▲| UNII = 533CV2ZCQL
| InChI = 1/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+
| InChIKey = CCRCUPLGCSFEDV-BQYQJAHWBN
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CCRCUPLGCSFEDV-BQYQJAHWSA-N
▲| SMILES = COC(=O)C=CC1=CC=CC=C1
| RTECS =
| MeSHName =
▲| ChEBI =
▲| KEGG_Ref = {{keggcite|changed|kegg}}
▲| KEGG = C06358
}}
|Section2={{Chembox Properties
| C=10|H=10|O=2
| Appearance =
| Density = 1.092 {{nbsp}}g/cm<sup>3</sup>
| MeltingPtC = 34 to 3834–38
| BoilingPtC = 261 to 262261–262
| Solubility = Insoluble
}}
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| FlashPtC = 110
| AutoignitionPt =
| GHS_ref=<ref>{{cite web |title=Methyl cinnamate |url=https://pubchem.ncbi.nlm.nih.gov/compound/637520#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| SPhrases = {{S22}} {{S24/25}}
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|317}}
| PPhrases = {{P-phrases|261|272|280|302+352|321|333+313|363|501}}
}}
}}
'''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 = 744744–9 | doi-access = free }}</ref> ''[[Eucalyptus olida]]'' has the highest known concentrations of methyl cinnamate (98%) with a 2-62–6% fresh weight yield in the leaf and twigs.<ref>{{Cite book | authorvauthors = Boland, D.J.DJ, Brophy, J.J.JJ, and A.P.N. ((House APN)) | title = Eucalyptus Leaf Oils | year = 1991 | isbn = 978-0-909605-69-68}}</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 | url = | journal = Biol. Bull. | volume = 164 | issue = 3| pages = 355–395 | jstor = 1541248 | url = https://www.biodiversitylibrary.org/part/35261 }}</ref>
 
[[File:Methyl cinnamate1.JPG|thumb|left|200px|Methyl cinnamate crystals extracted using steam distillation from ''Eucalyptus olida''.]]{{clear left}}
 
== List of plants that contain the chemical ==
* ''[[Eucalyptus olida]]'' 'Strawberry gumGum'
* ''[[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 Castle (Castilla Morada)
* ''Ocimum americanum'' cv. Purple Long-legged (Zancona morada)
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* ''[[Ocimum basilicum]]'' cv. Sweet Castle (Dulce de Castilla)
* ''Ocimum basilicum'' cv. White Compact (Blanca compacta)
* ''Ocimum basilicum'' cv. large green leaves (Verde{{lang|es|verde des horjas grandes}})
* ''[[Ocimum micranthum]]'' cv. Cinnamon (Canela)
* ''[[Ocimum minimum]]'' cv. Little Virgin (Virgen pequena)
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== Toxicology and safety ==
Moderately toxic by ingestion. The oral {{LD50}} for rats is 2610&nbsp;mg/kg.<ref>{{Cite journalcite book|author=Richard journalJ. Lewis|title= [[Food and Cosmetics Toxicology]]Additives Handbook| issue url= 13 https://books.google.com/books?id=nC7OGhzZn5YC&pg=PA304|year=1989|publisher=Springer pagesScience =& 681Business Media| year isbn= 1975978-0-442-20508-9|pages=304–}}</ref> It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.
It is combustible as a liquid, and when heated to decomposition it emits acrid smoke and irritating fumes.
 
==Compendial status==
* [[Food Chemicals Codex]]<ref name=ptm>{{cite web
| last = [[Therapeutic Goods Administration]]
| author-link = Therapeutic Goods Administration
| first =
| authorlink =
| coauthors =
| title = Approved Terminology for Medicines
| work =
| publisher =
| date = 1999
| 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 =
| accessdatearchive-date = 2922 JuneMay 20092006
| url-status = dead
}}</ref>
 
== See also ==
* [[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}}
<references/>
 
{{DEFAULTSORT:Methyl Cinnamate}}
[[Category:CinnamatesCinnamate esters]]
[[Category:Methyl esters]]
[[Category:Flavors]]
[[Category:AlkenesSweet-smelling chemicals]]
 
[[ja:ケイ皮酸メチル]]
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