FComEx: trans-Cinnamic acid (PC000148)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:50 UTC

Update date

2017-01-19 02:36:14 UTC

FoodComEx ID

PC000148

FoodDB Record

FDB008784

Chemical Information

Name

trans-Cinnamic acid

Description

Trans-cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acid can exist in both the cis and trans form, with the trans-form being most common. Trans-cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Trans-cinnamic acid occurs naturally in a number of plants. It is a sweet, balsam, or cinnamon tasting compound. Trans-cinnamic acid is characterized by a honey-like odor. Trans-cinnamic acid is found in a number of foods with the highest concentration found in chinese cinnamons (cinnamon bark), olives, and lingonberries and in a lower concentration in redcurrants, red raspberries, and corianders. Trans-cinnamic acid has also been detected, but not quantified in common oregano, pepper (spice), fennels, pomegranates, and european cranberries. Trans-cinnamic acid has also been shown to be a microbial metabolite as it is produced by microbes belonging to the Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas families (PMID: 16349793). In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine (PMID:20035037). Cinnamic acid is used in flavorings, the production of synthetic indigo, and certain pharmaceuticals. A major use of trans-cinnamic acid is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry.

CAS Number

140-10-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-2-Phenyl-2-propenoate	biospider
(2E)-2-Phenyl-2-propenoic acid	biospider
(2E)-3-Phenyl-2-propenoate	biospider
(2E)-3-Phenyl-2-Propenoic acid	biospider
(2e)-3-Phenylacrylate	Generator
(2e)-3-Phenylacrylic acid	ChEBI
(2E)-3-Phenylprop-2-enoate	biospider
(e)-3-Phenyl-2-propenoate	Generator
(E)-3-Phenyl-2-propenoic acid	biospider
(E)-3-Phenylacrylate	biospider
(E)-3-Phenylacrylic acid	biospider
(E)-3-Phenylprop-2-enoate	biospider
(E)-3-Phenylprop-2-enoic acid	biospider
(E)-Cinnamate	biospider
(E)-Cinnamic acid	biospider
2-Propenoic acid, 3-phenyl-, (E)-	biospider
Benzeneacrylate	Generator
Cinnamic acid, (E)-	biospider
PHENYLETHYLENECARBOXYLate	Generator
trans-β-Carboxystyrene	biospider
trans-3-Phenyl-2-propenoate	biospider
trans-3-Phenyl-2-propenoic acid	biospider
trans-3-Phenylacrylate	biospider
trans-3-Phenylacrylic acid	biospider
trans-b-Carboxystyrene	biospider
trans-beta-Carboxystyrene	biospider
trans-Cinnamate	biospider
trans-Cinnamic acid	biospider
trans-Zimtsaeure	ChEBI
trans-β-carboxystyrene	Generator

Chemical Formula

C9H8O2

IUPAC name

(2E)-3-phenylprop-2-enoic acid

InChI Identifier

InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

InChI Key

WBYWAXJHAXSJNI-VOTSOKGWSA-N

Isomeric SMILES

OC(=O)\C=C\C1=CC=CC=C1

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Styrene
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamic acid (CHEBI:35697 )
Monolignols (C00423 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	2.13	HANSCH,C ET AL. (1995)
Experimental Water Solubility	0.546 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 133°	DFC

Foods of Origin