ChemFOnt: Showing chemical card for cis-Cinnamic acid (CFc000335649)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:19 UTC

Chemfont ID

CFc000335649

Molecule Identification

Common Name

cis-Cinnamic acid

Definition

Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water. It is obtained from oil of cinnamon, or from balsams such as storax. cis-Cinnamic acid is found in chinese cinnamon.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2Z)-3-Phenyl-2-propenoic acid	ChEBI
(2Z)-3-Phenylacrylic acid	ChEBI
(Z)-3-Phenyl-2-propenoic acid	ChEBI
(Z)-Cinnamic acid	ChEBI
cis-beta-Carboxystyrene	ChEBI
cis-Zimtsaeure	ChEBI
(2Z)-3-Phenyl-2-propenoate	Generator
(2Z)-3-Phenylacrylate	Generator
(Z)-3-Phenyl-2-propenoate	Generator
(Z)-Cinnamate	Generator
cis-b-Carboxystyrene	Generator
cis-Β-carboxystyrene	Generator
Cinnamate	Generator
Cinnamic acid, 1-(13)C-labeled CPD	HMDB
Cinnamic acid, 13C-labeled CPD	HMDB
trans-Cinnamic acid	HMDB
(e)-Cinnamic acid, 2-(14)C-labeled CPD	HMDB
Cinnamic acid, (Z)-isomer	HMDB
Cinnamic acid, (trans)-(e)-isomer	HMDB
Cinnamic acid, 14C-labeled CPD	HMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomer	HMDB
Cinnamic acid, sodium salt	HMDB
Cinnamic acid, sodium salt(Z)-isomer	HMDB
Sodium cinnamate	HMDB
e-Z Cinnamic acid	HMDB
Cinnamic acid, 2-(13)C-labeled CPD	HMDB
Cinnamic acid, 2-(14)C-labeled CPD	HMDB
Cinnamic acid, 3-(14)C-labeled CPD	HMDB
Cinnamic acid, radical ion(1-)	HMDB
e-Cinnamic acid	HMDB
Cinnamic acid, 1-14C-labeled CPD	HMDB
Cinnamic acid, 14C-labeled CPD (e)-isomer	HMDB
Cinnamic acid, 3H-labeled CPD (e)-isomer	HMDB
Cinnamic acid, ion(1-)	HMDB
Cinnamic acid, ion(1-)-(e)-isomer	HMDB
Cinnamic acid, nickel (+2) salt	HMDB
Cinnamic acid, potassium salt	HMDB
Cinnamic acid, sodium salt(e)-isomer	HMDB
Cinnamic acid, zinc salt(e)-isomer	HMDB
Tritium labeled (e)-cinnamic acid	HMDB
Tritium labeled (Z)-cinnamic acid	HMDB
(e)-3-Phenyl-2-propenoate	HMDB
(e)-3-Phenyl-2-propenoic acid	HMDB
3-Phenyl-2-propenoate	HMDB
3-Phenyl-2-propenoic acid	HMDB
3-Phenyl-acrylate	HMDB
3-Phenyl-acrylic acid	HMDB
3-Phenylacrylate	HMDB
3-Phenylacrylic acid	HMDB
3-Phenylpropenoate	HMDB
3-Phenylpropenoic acid	HMDB
Benzenepropenoate	HMDB
Benzenepropenoic acid	HMDB
Benzylideneacetic acid	HMDB
beta-Phenylacrylic acid	HMDB
Cinnamylic acid	HMDB
Phenylacrylate	HMDB
Phenylacrylic acid	HMDB
cis-Cinnamate	HMDB
(Z)-3-Phenylacrylic acid	HMDB
Allocinnamic acid	HMDB
Isocinnamic acid	HMDB
cis-Cinnamic acid	HMDB
Β-phenylacrylic acid	HMDB
Cinnamic acid	HMDB

Chemical Formula

C₉H₈O₂

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

IUPAC Name

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

Traditional Name

cis-cinnamic acid

CAS Registry Number

102-94-3

SMILES

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

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-SREVYHEPSA-N

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:35699 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000567)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.14	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.06 m³·mol⁻¹	ChemAxon
Polarizability	15.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon