benzyl cinnamate

{{Chembox

| ImageFile = Benzyl cinnamate.svg

| ImageSize = 220px

| ImageAlt = Skeletal formula of benzyl cinnamate

| ImageFile1 = Benzyl cinnamate 3D spacefill.png

| ImageSize1 = 220

| ImageAlt1 = Space-filling model of the benzyl cinnamate molecule

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

| OtherNames = Benzyl cinnamate
Cinnamein
Benzyl cinnamoate
Benzyl 3-phenylpropenoate
3-Phenyl-2-propenoic acid phenylmethyl ester
Cinnamic acid benzyl ester

|Section1={{Chembox Identifiers

| CASNo = 103-41-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = V67O3RO97U

| PubChem = 5273469

| ChemSpiderID = 4437893

| InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+

| InChIKey= NGHOLYJTSCBCGC-VAWYXSNFSA-N

| SMILES = C1=CC=C(C=C1)COC(=O)C=CC2=CC=CC=C2}}

|Section2={{Chembox Properties

| C=16|H=14|O=2

| Appearance = White to pale yellow solid{{cite web | url = http://www.fao.org/ag/agn/jecfa-flav/details.html?flavId=3497 | publisher = Food and Agriculture Organization | title = Specifications for Flavourings | access-date = 2014-02-20 | archive-date = 2015-09-24 | archive-url = https://web.archive.org/web/20150924045655/http://www.fao.org/ag/agn/jecfa-flav/details.html?flavId=3497 | url-status = dead }}

| Density =

| MeltingPtC = 34–37

| MeltingPt_ref = {{cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/234214?lang=en | publisher = Sigma-Aldrich | title = Benzyl cinnamate }}

| BoilingPtC = 195–200

| BoilingPt_notes = 5{{nbsp}}mmHg

| Solubility = Insoluble

| Solvent1 = ethanol

| Solubility1 = 125 g/L

| Solvent2 = glycerin

| Solubility2 = Insoluble

| Solvent3 = propylene glycol

| Solubility3 = Insoluble

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Benzyl cinnamate is the chemical compound which is the ester derived from cinnamic acid and benzyl alcohol.

Natural occurrence

Balsam is the major producer of benzyl cinnamate.{{citation | entry=BENZYL CINNAMATE | author=George A. Burdock | title=Fenaroli's Handbook of Flavor Ingredients | edition=6th | publisher=CRC Press | year=2010 | pages=147–148}} It is used as an ingredient in the medicated cream product Sudocrem.{{cite web |title=Sudocrem Antiseptic Healing Cream - Summary of Product Characteristics (SmPC) - (emc) |url=https://www.medicines.org.uk/emc/product/8860/smpc/ |website=www.medicines.org.uk |access-date=11 June 2021}}

Uses

It is used as a flavoring agent.

It is used pharmaceutically as an antibacterial and antifungal.{{cite journal |last1=Korošec |first1=B. |last2=Sova |first2=M. |last3=Turk |first3=S. |last4=Kraševec |first4=N. |last5=Novak |first5=M. |last6=Lah |first6=L. |last7=Stojan |first7=J. |last8=Podobnik |first8=B. |last9=Berne |first9=S. |last10=Zupanec |first10=N. |last11=Bunc |first11=M. |last12=Gobec |first12=S. |last13=Komel |first13=R. |title=Antifungal activity of cinnamic acid derivatives involves inhibition of benzoate 4-hydroxylase (CYP53) |journal=Journal of Applied Microbiology |date=2014 |volume=116 |issue=4 |pages=955–966 |doi=10.1111/jam.12417 |pmid=24314266 |language=en |issn=1365-2672|doi-access= }}

References

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