AFCDB: o-Coumaric acid (FDB011258)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:33 UTC

Update date

2019-11-26 03:04:44 UTC

Primary ID

FDB011258

Secondary Accession Numbers

FDB002589

Chemical Information

FooDB Name

o-Coumaric acid

Description

2-Hydroxycinnamic acid, also known as 2-coumarate or 2-coumaric acid, 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. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as corns (Zea mays), hard wheats (Triticum durum), and olives (Olea europaea) and in a lower concentration in pears (Pyrus communis), grape wine, and dates (Phoenix dactylifera). 2-Hydroxycinnamic acid has also been detected, but not quantified in, several different foods, such as turmerics (Curcuma longa), sesames (Sesamum orientale), evening primroses (Oenothera biennis), common peas (Pisum sativum), and german camomiles (Matricaria recutita). This could make 2-hydroxycinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxycinnamic acid.

CAS Number

583-17-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.15 g/L	ALOGPS
logP	1.9	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.04	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	16.11 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H8O3

IUPAC name

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

InChI Identifier

InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+

InChI Key

PMOWTIHVNWZYFI-AATRIKPKSA-N

Isomeric SMILES

OC(=O)\C=C\C1=CC=CC=C1O

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

phenols (CHEBI:18125 )
2-coumaric acid (CHEBI:18125 )
Monolignols (C01772 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

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	pKa1 3.7 (30°, 1.0M LiCl)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014j-8900000000-8e96a9ec1b9d035d3edb	2015-03-01	View Spectrum
GC-MS	trans-o-Coumaric acid, 2 TMS, GC-MS Spectrum	splash10-0002-0910000000-9e0bdbf6d6389288e318	Spectrum
GC-MS	trans-o-Coumaric acid, 2 TMS, GC-MS Spectrum	splash10-00dj-9710000000-829ded288e3ec8312160	Spectrum
GC-MS	trans-o-Coumaric acid, 2 TMS, GC-MS Spectrum	splash10-00dj-9710000000-8fb7bb39d916f7402980	Spectrum
GC-MS	trans-o-Coumaric acid, 2 TMS, GC-MS Spectrum	splash10-0296-2941000000-b85ebef8eb8c276f220f	Spectrum
GC-MS	trans-o-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014i-9800000000-3650ee76a1293cba7523	Spectrum
GC-MS	trans-o-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-9e0bdbf6d6389288e318	Spectrum
GC-MS	trans-o-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-00dj-9710000000-829ded288e3ec8312160	Spectrum
GC-MS	trans-o-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-00dj-9710000000-8fb7bb39d916f7402980	Spectrum
GC-MS	trans-o-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-0296-2941000000-b85ebef8eb8c276f220f	Spectrum
GC-MS	trans-o-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-c783499d6f33717b71ca	Spectrum
Predicted GC-MS	trans-o-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014j-2900000000-3a06c14b7e8999427ad9	Spectrum
Predicted GC-MS	trans-o-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00y3-6390000000-a82ff5bd6498e3c478ea	Spectrum
Predicted GC-MS	trans-o-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-9e4823d321cfe6f5e5a4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-efd5de4e7fe4032816f6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-0900000000-44e81c2c735a93efc7d7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014l-7900000000-977a2bb08508d16be531	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fdn-4900000000-dcfe2b032cf6bbee16b3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-adbaf7b04487b18191e0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-d368e3c354c7b05a949f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-efd5de4e7fe4032816f6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-44e81c2c735a93efc7d7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014l-7900000000-a641b2c2528f829e8ac1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-adbaf7b04487b18191e0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0900000000-2ca69c9285dedaa2f424	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0900000000-55078e8ec591840fb594	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0fdn-4900000000-95f5386456c1c353a111	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-bf00664334bbd7d7d91d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-ba0915b2f87da989c92b	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-fd2da9ac5865a50fc50c	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gdu-9300000000-3baee6b4124fba79677e	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-69f05779283af436427d	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-1900000000-0bc76f24c2abf6670fc0	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-a2981a5342a71b94ce69	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-972f865a96261dcb891a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0900000000-dfdb5072d39445a67f3a	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

462

DrugBank ID

DB01650

HMDB ID

HMDB02641

CRC / DFC (Dictionary of Food Compounds) ID

GKS64-L:GKS64-L

EAFUS ID

Not Available

Dr. Duke ID

O-COUMARIC-ACID|2-HYDROXYCINNAMIC-ACID|O-HYDROXYCINNAMIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00002729

HET ID

2HC

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Coumaric_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allelopathic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	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
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

o-Coumaric acid (FDB011258)

Structure for FDB011258 (o-Coumaric acid)