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Showing Compound Butyl 3-O-caffeoylquinate (FDB013104)

Record Information
Version1.0
Creation date2010-04-08 22:10:32 UTC
Update date2019-11-26 03:07:58 UTC
Primary IDFDB013104
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameButyl 3-O-caffeoylquinate
DescriptionButyl 3-O-caffeoylquinate 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. Butyl 3-O-caffeoylquinate has been detected, but not quantified in, fruits. This could make butyl 3-O-caffeoylquinate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Butyl 3-O-caffeoylquinate.
CAS Number132741-56-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Butyl 3-O-caffeoylquinic acidGenerator
Butyl 3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acidHMDB
Butyl 3-O-caffeoylquinatemanual
Predicted Properties
PropertyValueSource
Water Solubility1.23 g/LALOGPS
logP1ALOGPS
logP1.2ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity101.88 m³·mol⁻¹ChemAxon
Polarizability41.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H26O9
IUPAC namebutyl 3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate
InChI IdentifierInChI=1S/C20H26O9/c1-2-3-8-28-19(26)20(27)10-15(23)18(25)16(11-20)29-17(24)7-5-12-4-6-13(21)14(22)9-12/h4-7,9,15-16,18,21-23,25,27H,2-3,8,10-11H2,1H3/b7-5-
InChI KeyVNLREARKISTOAD-ALCCZGGFSA-N
Isomeric SMILESCCCCOC(=O)C1(O)CC(O)C(O)C(C1)OC(=O)\C=C/C1=CC(O)=C(O)C=C1
Average Molecular Weight410.415
Monoisotopic Molecular Weight410.15768243
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
  • Quinic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.53%; H 6.39%; O 35.08%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSButyl 3-O-caffeoylquinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-7219000000-690c22dc6ee5ec407cc0Spectrum
Predicted GC-MSButyl 3-O-caffeoylquinate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-5204097000-325471ef4f9ea9d27e4dSpectrum
Predicted GC-MSButyl 3-O-caffeoylquinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4987700000-4c3f0400b88b886b27cc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-7933000000-290741306b8d2cee65b32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-3910000000-4e33f01809d7c9cee0282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3758900000-e1c57a5b349a13da717c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0m99-1934000000-2fda20bb1fd2b0ca48b12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-1900000000-5114145a9cf879274e822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2338900000-c9e19d81ae124ce4677f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ec-2914000000-5d853dcee5749b930b2b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-0900000000-82ddcaed709cb85494942021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a71-0488900000-31de27a91bac604b080c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bj-0974100000-9d09677ec978fa3c71572021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-8932000000-88b4d46134a728bf9b562021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34588
CRC / DFC (Dictionary of Food Compounds) IDCMM44-X:HOP39-F
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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