Showing Compound Ethyl cinnamate (FDB012002)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:56 UTC

Update date

2019-11-26 03:05:56 UTC

Primary ID

FDB012002

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ethyl cinnamate

Description

Ethyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Ethyl cinnamate is a sweet, balsam, and berry tasting compound. Ethyl cinnamate is found, on average, in the highest concentration within red wine. Ethyl cinnamate has also been detected, but not quantified in, several different foods, such as ceylon cinnamons (Cinnamomum verum), evergreen blackberries (Rubus laciniatus), tamarinds (Tamarindus indica), blackberries (Rubus), and tarragons (Artemisia dracunculus). This could make ethyl cinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Ethyl cinnamate.

CAS Number

4192-77-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(e)-Ethyl cinnamate	HMDB
(e)-ethyl cinnamate	biospider
2-Propenoic acid, 3-phenyl-, ethyl ester, (E)-	biospider
3-Phenyl-ethyl ester(e)-2-propenoic acid	HMDB
Ethyl (2E)-3-phenyl-2-propenoate	HMDB
Ethyl (2E)-3-phenylacrylate	HMDB
Ethyl (2Z)-3-phenylprop-2-enoic acid	Generator
Ethyl (e)-cinnamate	HMDB
Ethyl cinnamate, trans	HMDB
Ethyl cinnamic acid	Generator

Showing 1 to 10 of 14 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.87	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.58 m³·mol⁻¹	ChemAxon
Polarizability	19.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H12O2

IUPAC name

ethyl (2Z)-3-phenylprop-2-enoate

InChI Identifier

InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8-

InChI Key

KBEBGUQPQBELIU-HJWRWDBZSA-N

Isomeric SMILES

CCOC(=O)\C=C/C1=CC=CC=C1

Average Molecular Weight

176.2118

Monoisotopic Molecular Weight

176.083729628

Classification

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Poaceae

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp24 159°	DFC
Charge	Not Available
Density	d2525 1.05	DFC
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 74.98%; H 6.86%; O 18.16%	DFC
Melting Point	Mp 12°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fai-3900000000-a8d987a548c9fa6c7f2d	Spectrum
Predicted GC-MS	Ethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-061762de8ea8d97b5cfa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4900000000-c561bd073358d027fd92	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufu-9500000000-f3a99db2bb06534a646b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-b7e60492dd7bc9500be1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-2240e17326bb0662c91c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fba-3900000000-0d609d9bc26a486298ca	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-ba8ba15dbd02ca4eec9e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-1900000000-935e6ce292933740c493	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-6900000000-f309c938a129dc5470f6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-d4773b1f6c6f68c13fae	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-002df14c18a57d0f27a0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-9500000000-502a9fa131a679c46ac9	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4447700

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5284656

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33834

CRC / DFC (Dictionary of Food Compounds) ID

HCV54-E:HCL40-Z

EAFUS ID

1162

Dr. Duke ID

CINNAMIC-ACID-ETHYL-ESTER|ETHYL-CINNAMATE

BIGG ID

Not Available

KNApSAcK ID

C00035614

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Flavornet: 103-36-6

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE

Showing 1 to 3 of 3 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
berry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cinnamon	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
flower	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
honey	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
plum	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.