Methyl cinnamate

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 423505240

| Reference = [http://www.thegoodscentscompany.com/data/rw1417571.html Methyl cinnamate], at goodscents.com[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/173282 Methyl cinnamate], at Sigma-Aldrich

| ImageFile = Methyl cinnamate.png

| ImageSize = 190px

| ImageAlt = Skeletal formula of methyl cinnamate

| ImageFile1 = Methyl cinnamate 3D spacefill.png

| ImageAlt1 = Ball-and-stick model of the methyl cinnamate molecule

| PIN = Methyl (2E)-3-phenylprop-2-enoate

| OtherNames = Methyl cinnamate

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 103-26-4

| ChEBI = 6857

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 55060

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21105944

| EINECS = 203-093-8

| KEGG_Ref = {{keggcite|correct|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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = CCRCUPLGCSFEDV-BQYQJAHWSA-N

| 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/cm³

| MeltingPtC = 34–38

| BoilingPtC = 261–262

| Solubility = Insoluble

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt = >

| FlashPtC = 110

| AutoignitionPt =

| GHS_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}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|317}}

| PPhrases = {{P-phrases|261|272|280|302+352|321|333+313|363|501}}

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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.{{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 }} Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs.{{Cite book | vauthors = Boland DJ, Brophy JJ,((House APN)) | title = Eucalyptus Leaf Oils | year = 1991 | isbn = 978-0-909605-69-8}}

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 bees, such as Aglae caerulea.{{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 }}

File:Methyl cinnamate1.JPG{{clear left}}