Showing Compound m-Coumaric acid (FDB002590)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2019-11-26 02:57:39 UTC

Primary ID

FDB002590

Secondary Accession Numbers

FDB002591

Chemical Information

FooDB Name

m-Coumaric acid

Description

Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. m-Coumaric acid is found in many foods, some of which are corn, garden tomato (variety), grape wine, and beer.

CAS Number

588-30-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
3-Coumaric acid	ChEBI
m-Hydroxycinnamic acid	ChEBI
trans-3-Hydroxycinnamate	ChEBI
trans-3-Hydroxycinnamic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoate	Kegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
(2E)-3-(3-Hydroxyphenyl)acrylate	Generator
(e)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
3-Coumarate	Generator
m-Hydroxycinnamate	Generator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid	Generator
m-Coumarate	Generator
3'-Hydroxycinnamate	HMDB
3'-Hydroxycinnamic acid	HMDB
3-(3-Hydroxyphenyl)-2-propenoate	HMDB
3-(3-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(3-Hydroxyphenyl)acrylate	HMDB
3-(3-Hydroxyphenyl)acrylic acid	HMDB
3-(3-Hydroxyphenyl)acrylsaeure	HMDB
3-(3-Hydroxyphenyl)prop-2-enoate	HMDB
3-(3-Hydroxyphenyl)prop-2-enoic acid	HMDB
3-Hydroxycinnamate	HMDB
3-Hydroxycinnamic acid	HMDB
m-Hydroxy-cinnamate	HMDB
m-Hydroxy-cinnamic acid	HMDB
trans-3-Coumaric acid	HMDB
3-Coumaric acid, (e)-isomer	HMDB
Meta-coumaric acid	HMDB
(e)-3-(3-Hydroxyphenyl)acrylic acid	HMDB
(e)-3-Hydroxycinnamic acid	HMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-m-Coumaric acid	HMDB
trans-m-Hydroxycinnamic acid	HMDB
trans-3-Coumarate	HMDB
m-Coumaric acid	HMDB
(2e)-3-(3-Hydroxyphenyl)acrylate	Generator
m-Cumaric acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	1.04 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.37 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	Yes	ChemAxon

Chemical Formula

C9H8O3

IUPAC name

(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid

InChI Identifier

InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+

InChI Key

KKSDGJDHHZEWEP-SNAWJCMRSA-N

Isomeric SMILES

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

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

Classification

Description

belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

3-coumaric acid (CHEBI:32357 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant:

Poaceae

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 65.85%; H 4.91%; O 29.24%	DFC
Melting Point	Not Available
Boiling Point	Not Available
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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udl-1691000000-331053d0d0b85549ac0b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udl-1691000000-331053d0d0b85549ac0b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1891000000-049e1d80dd47b23e8c28	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02t9-2900000000-91ffd4c10eaed6a17632	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00y3-6390000000-f1a30e2fb9cd1fb11341	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03xr-0900000000-4259219e89806dfe2602	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-014i-4900000000-2157a17ec65ead35585e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00kf-9300000000-3325dd31a734dd4659bb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-be33d196fbb525019f07	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-d256885fb0f35d3d6680	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-be33d196fbb525019f07	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-d256885fb0f35d3d6680	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-b5ad37fb931b464df7d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-1900000000-c66c146ee9509bf8a413	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-9700000000-fcc332df0fcb818fe0e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-408ac0dd815354188750	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-146bae2da386ca2d4f1a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-3900000000-235b38f342376d1c9f90	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-7900000000-61ee2ad0ad164a1f7550	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer