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3-p-Coumaroylquinic acid (FDB000866)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2019-08-01 18:39:54 UTC
Primary IDFDB000866
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-p-Coumaroylquinic acid
Description3-O-p-Coumaroylquinic acid belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 3-O-p-Coumaroylquinic acid is found, on average, in the highest concentration within apples (Malus pumila). 3-O-p-Coumaroylquinic acid has also been detected, but not quantified in, several different foods, such as bitter gourds (Momordica charantia), spelts (Triticum spelta), canola, oxheart cabbages (Brassica oleracea var. conica), and rocket salad (ssp.). This could make 3-O-p-coumaroylquinic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-O-p-Coumaroylquinic acid.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted PropertiesNot Available
Chemical FormulaC16H18O8
IUPAC name
InChI IdentifierInChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14+,16-/m1/s1
InChI KeyBMRSEYFENKXDIS-QHAYPTCMSA-N
Isomeric SMILESO[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O
Average Molecular Weight338.3093
Monoisotopic Molecular Weight338.100167552
Classification
Description Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid ester
  • Quinic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • Phenol
  • Fatty acid ester
  • Cyclohexanol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Enoate ester
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.80%; H 5.36%; O 37.83%DFC
Melting PointMp 247-248°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -53.6 (c, 1.04 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID8121397
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9945785
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID476
DrugBank IDNot Available
HMDB IDHMDB29681
CRC / DFC (Dictionary of Food Compounds) IDBKL56-Y:BKL56-Y
EAFUS IDNot Available
Dr. Duke ID3-O-P-COUMAROYL-QUINIC-ACID|3-O-COUMARYLQUINIC-ACID|P-COUMARYL-QUINIC-ACID|TRANS-P-COUMAROYLQUINIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029511
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.