Showing Compound Benzyl cinnamate (FDB020007)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:44 UTC

Update date

2019-11-26 03:18:17 UTC

Primary ID

FDB020007

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Benzyl cinnamate

Description

Benzyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Benzyl cinnamate is a sweet, apricot, and balsam tasting compound. Benzyl cinnamate is found, on average, in the highest concentration within cumins (Cuminum cyminum). This could make benzyl cinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl cinnamate.

CAS Number

103-41-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Benzyl cinnamic acid	Generator
2-Propenoic acid, 3-phenyl-, phenylmethyl ester	HMDB
3-Phenyl-2-propenoic acid phenylmethyl ester	HMDB
Benzyl (2E)-3-phenyl-2-propenoate	HMDB
Benzyl 3-phenylpropenoate	HMDB
Benzyl alcohol cinnamic ester	HMDB
Benzyl alcohol, cinnamate	HMDB
Benzyl laquo gammaraquo -phenylacrylate	HMDB
Benzylcinnamate	HMDB
Benzylester kyseliny skoricove	HMDB
Cinnamein	HMDB
Cinnamic acid, benzyl ester	HMDB
FEMA 2142	HMDB
trans-Cinnamic acid benzyl ester	HMDB
Benzyl (2Z)-3-phenylprop-2-enoic acid	Generator
Benzyl cinnamate	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.03	ALOGPS
logP	4.24	ChemAxon
logS	-4.8	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	5	ChemAxon
Refractivity	72.44 m³·mol⁻¹	ChemAxon
Polarizability	26.73 Å³	ChemAxon
Number of Rings	2	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

C16H14O2

IUPAC name

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

InChI Identifier

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-

InChI Key

NGHOLYJTSCBCGC-QXMHVHEDSA-N

Isomeric SMILES

O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1

Average Molecular Weight

238.2812

Monoisotopic Molecular Weight

238.099379692

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

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 80.65%; H 5.92%; O 13.43%	DFC
Melting Point	Mp 37-39°	DFC
Boiling Point	Bp5 195-200°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Benzyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f6x-9600000000-b730105b1586b6466dfd	Spectrum
Predicted GC-MS	Benzyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Benzyl 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	splash10-000i-1590000000-d59e744cc0df894ea1e3	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2920000000-6c944a45122d144c5be2	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9700000000-0cef35c32391ca819098	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-0890000000-0c8dd31dd420da8aaa72	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004s-1910000000-475c63c855b416c3406c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3900000000-2e7d267ea7a7698e4165	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-4398f96ca62f3f4192ee	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054x-7930000000-651e889cc06e8e51210c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-7920000000-7112ddc3c777a8c0212f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1390000000-66fcd7f42ef305268409	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-5920000000-11bd2d1f6032302ebf18	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9600000000-78322ccdb4fc9f711f78	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

21391699

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

15558051

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40286

CRC / DFC (Dictionary of Food Compounds) ID

HCV54-E:MJJ14-K

EAFUS ID

316

Dr. Duke ID

BENZYL-CINNAMATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1014311

SuperScent ID

5273469

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
irritant			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
chocolate	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
apricot	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cherry	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.
peach	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
pineapple	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.