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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:59 UTC
Update Date2023-02-21 17:16:26 UTC
HMDB IDHMDB0002641
Secondary Accession Numbers
  • HMDB02641
Metabolite Identification
Common Name2-Hydroxycinnamic acid
Description2-coumaric acid, also known as o-coumaric acid, is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. It is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. 2-Hydroxycinnamic 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 has been found in a few different foods, such as corns, hard wheats, and olives and in a lower concentration in pomegranates, american cranberries, and peanuts. 2-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as carrots, soy beans, ryes, rye bread, and turmerics.
Structure
Thumb
Synonyms
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional NameO-coumaric acid
CAS Registry Number614-60-8
SMILES
OC(=O)\C=C\C1=C(O)C=CC=C1
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 KeyPMOWTIHVNWZYFI-AATRIKPKSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point348.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility27090 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.430 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available127.336http://allccs.zhulab.cn/database/detail?ID=AllCCS00000435
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01650
Phenol Explorer Compound ID462
FooDB IDFDB011258
KNApSAcK IDC00002729
Chemspider ID553146
KEGG Compound IDC01772
BioCyc ID2-COUMARATE
BiGG IDNot Available
Wikipedia LinkO-Coumaric_acid
METLIN ID6727
PubChem Compound637540
PDB IDNot Available
ChEBI ID18125
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1176751
References
Synthesis ReferenceAdams, Roger; Bockstahler, Theodore E. Preparation and reactions of o-hydroxycinnamic acids and esters. Journal of the American Chemical Society (1952), 74 5346-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]