Showing Compound Methyl cinnamate (FDB012001)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:56 UTC

Update date

2019-11-26 03:05:55 UTC

Primary ID

FDB012001

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyl cinnamate

Description

Occurs in essential oils e.g. from Ocimum and Alpinia subspecies Also present in various fruits, e.g. guava, feijoa, strawberry. Flavouring agent 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. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2-6% fresh weight yield in the leaf and twigs. Methyl cinnamate is found in many foods, some of which are chinese cinnamon, fruits, herbs and spices, and sweet basil.

CAS Number

103-26-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-propenoic acid, 3-phenyl-, methyl ester, (2E)-	biospider
2-Propenoic acid, 3-phenyl-, methyl ester, (E)-	biospider
3-Phenyl-methyl ester(2E)-2-propenoic acid	HMDB
3-Phenyl-methyl ester(2e)-2-propenoic acid	HMDB
3-Phenyl-methyl ester(e)-2-propenoic acid	HMDB
Cinnamic acid, methyl ester, (e)-	biospider
Cinnamic acid,methyl ester (trans)	HMDB
FEMA 2698	HMDB
Methyl (2E)-3-phenyl-2-propenoate	HMDB
Methyl (2E)-3-phenylacrylate	HMDB

Showing 1 to 10 of 18 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.52	ChemAxon
logS	-2.9	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	3	ChemAxon
Refractivity	47.83 m³·mol⁻¹	ChemAxon
Polarizability	17.51 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

C10H10O2

IUPAC name

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

InChI Identifier

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

InChI Key

CCRCUPLGCSFEDV-FPLPWBNLSA-N

Isomeric SMILES

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

Average Molecular Weight

162.1852

Monoisotopic Molecular Weight

162.068079564

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
Fatty acyl
Benzenoid
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp 263°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	2.62	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 74.06%; H 6.21%; O 19.73%	DFC
Melting Point	Mp 36°	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	Methyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ue9-2900000000-fa70434583f14596679d	Spectrum
Predicted GC-MS	Methyl 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	splash10-01q9-0900000000-14824eb7072537bd3530	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gx0-2900000000-d9f3a46dc13424ed6d6b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9700000000-786bab6ed4a26977fbf1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ef3e4fba71ee6c0e61fa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-0900000000-25c7a5be399d9bcc6481	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-1900000000-fdff058008260fe95cbb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-0900000000-b6bdcd0fedc54834c9e6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-20d806534be8d5a510db	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-f637efaadb9d92581a8a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-3285e0b323d2266782ae	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2900000000-abd0c0c325ee40da24cb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9400000000-3c5a8c04f990bda44645	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4933863

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

6428458

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33833

CRC / DFC (Dictionary of Food Compounds) ID

HCV54-E:HCL39-F

EAFUS ID

2290

Dr. Duke ID

CINNAMIC-ACID-METHYL-ESTER|METHYL-CINNAMATE|(E)-METHYL-CINNAMATETRANS-CINNAMIC-ACID-METHYL-ESTER

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

103-26-4

GoodScent ID

rw1417571

SuperScent ID

Not Available

Wikipedia ID

Methyl_cinnamate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

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
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Showing 1 to 5 of 5 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.
cherry	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
strawberry	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 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.