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Record Information

Version

2.0

Creation Date

2012-08-09 09:16:11 -0600

Update Date

2015-09-13 15:15:33 -0600

Secondary Accession Numbers

ECMDB21422

Identification

Name:

Cinnamic acid

Description

Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. It has a melting point of 133 degree centigrade and a boiling point of 300 degree centigrade. It is an intermediate in the degradation of aromatic compounds in E. coli and is a substrate for several dioxygenases.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(E)-3-phenyl-2-propenoate
(E)-3-phenyl-2-propenoic acid
3-Phenyl-2-propenoate
3-Phenyl-2-propenoic acid
3-phenyl-acrylate
3-phenyl-acrylic acid
3-Phenylacrylate
3-Phenylacrylic acid
3-phenylpropenoate
3-phenylpropenoic acid
b-Phenylacrylate
b-Phenylacrylic acid
Benzenepropenoate
Benzenepropenoic acid
Benzylideneacetate
Benzylideneacetic acid
beta-Phenylacrylate
Beta-Phenylacrylic acid
Cinnamate
Cinnamylate
Cinnamylic acid
Phenylacrylate
Phenylacrylic acid
β-Phenylacrylate
β-Phenylacrylic acid

Chemical Formula:

C₉H₈O₂

Weight:

Average: 148.1586
Monoisotopic: 148.0524295

InChI Key:

WBYWAXJHAXSJNI-SREVYHEPSA-N

InChI:

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

CAS number:

621-82-9

IUPAC Name:

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

Traditional IUPAC Name:

cis-cinnamic acid

SMILES:

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

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 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

132-135 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	0.57 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP:	2.13 [HANSCH,C ET AL. (1995)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Cinnamic acid + NADH + Oxygen <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1900000000-f00ddafc38ffb949fd1f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-7930000000-f3ac0a061fb66ec84b5d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-066s-4900000000-f4bfd33daf0938375a0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0udi-0900000000-d93fb5a9c15682c1e6ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-004i-9000000000-9be1ef1ea4500691cb22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b4400af8b5aad0d8d323	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-9700000000-7d7dbe711d881767830e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-20d69cc859de39f18004	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-1357b63887db6df1be7a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0900000000-b8c6ecaf3fa85d1487a6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-7900000000-0805b8dbbbd2777f28c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-6e7b31576f8ffd356252	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f92-0900000000-c5fb484b178fce86b596	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-1900000000-36b618a3b50dc51ff302	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-5a19a7768eb87376d23c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-138b8c24fd394024a31a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-dd9a9ae0caad4bca05c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-530f30f323b6e6a53394	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-648b395c048d84ce7d9a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9600000000-cb54ab97d7414eccc874	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kukongviriyapan V, Phromsopha N, Tassaneeyakul W, Kukongviriyapan U, Sripa B, Hahnvajanawong V, Bhudhisawasdi V: Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Xenobiotica. 2006 Jan;36(1):15-28. Pubmed: 16507510
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

An, Hong; He, Xifeng; Fu, Jing. Synthesis of cinnamic acid. Huagong Shikan (2005), 19(7), 32-33, 41.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	27386
HMDB ID	HMDB00567
Pubchem Compound ID	444539
Kegg ID	C10438
ChemSpider ID	10286933
Wikipedia	Cinnamic acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. 3-phenylpropionate/cinnamic acid dioxygenase subunit alpha

General function:: Involved in iron ion binding
Specific function:: Part of the multicomponent 3-phenylpropionate dioxygenase. Converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively
Gene Name:: hcaE
Uniprot ID:: P0ABR5
Molecular weight:: 51109

Reactions

3-phenylpropanoate + NADH + O(2) = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD(+).
(2E)-3-phenylprop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NAD(+).

Protein Details

2. 3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunit

General function:: Involved in oxidoreductase activity
Specific function:: Part of the multicomponent 3-phenylpropionate dioxygenase, that converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP- dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively. This protein seems to be a 2Fe-2S ferredoxin
Gene Name:: hcaC
Uniprot ID:: P0ABW0
Molecular weight:: 11329

Protein Details

3. 3-phenylpropionate/cinnamic acid dioxygenase subunit beta

General function:: Involved in 3-phenylpropionate dioxygenase activity
Specific function:: Part of the multicomponent 3-phenylpropionate dioxygenase. Converts 3-phenylpropionic acid (PP) and cinnamic acid (CI) into 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol), respectively
Gene Name:: hcaF
Uniprot ID:: Q47140
Molecular weight:: 20579

Reactions

3-phenylpropanoate + NADH + O(2) = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD(+).
(2E)-3-phenylprop-2-enoate + NADH + O(2) = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NAD(+).

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Cinnamic acid (M2MDB001817)

Structure for #<Compound:0xafa09e98>

Enzymes

Reactions

Reactions