Back to Compounds

Cryptochlorogenic acid (FDB002561)

Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2020-02-24 19:10:32 UTC
Primary IDFDB002561
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCryptochlorogenic acid
DescriptionCryptochlorogenic acid, also known as 4-caffeoylquinic acid or 4-O-(e)-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. Cryptochlorogenic acid is found, on average, in the highest concentration within a few different foods, such as coffees (Coffea), robusta coffees (Coffea canephora), and arabica coffees (Coffea arabica) and in a lower concentration in sour cherries (Prunus cerasus), sweet cherries (Prunus avium), and green tea. Cryptochlorogenic acid has also been detected, but not quantified in, several different foods, such as cereals and cereal products, yali pears (Pyrus × bretschneideri), grape wine, asian pears (Pyrus pyrifolia), and red raspberries (Rubus idaeus). This could make cryptochlorogenic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cryptochlorogenic acid.
CAS Number905-99-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.12 g/LALOGPS
logP0.17ALOGPS
logP-0.27ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.23 m³·mol⁻¹ChemAxon
Polarizability34.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H18O9
IUPAC name(1S,3R,4S,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid
InChI IdentifierInChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
InChI KeyGYFFKZTYYAFCTR-JUHZACGLSA-N
Isomeric SMILESO[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O
Average Molecular Weight354.3087
Monoisotopic Molecular Weight354.095082174
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
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Hydroxy acid
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.24%; H 5.12%; O 40.64%DFC
Melting PointMp 182-184°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -75 (-54) (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCryptochlorogenic acid, 6 TMS, GC-MS Spectrumsplash10-0a4i-1798000000-4dd46c95bc0c59c9ca75Spectrum
GC-MSCryptochlorogenic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-1798000000-4dd46c95bc0c59c9ca75Spectrum
Predicted GC-MSCryptochlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002u-9823000000-7c2cbba3801b77cf9872Spectrum
Predicted GC-MSCryptochlorogenic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-8524089000-a6943a4218902cf3594eSpectrum
Predicted GC-MSCryptochlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCryptochlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0900000000-5102380fa7d54414c5eb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Negativesplash10-007c-0900000000-c9ca94e205b1f98fc6f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00fu-0910000000-1b593c8d67bb01bed1312021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0fmi-0913000000-de26d4b9f40a73cbe42a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-5dc06058803dd571b5b92021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0819000000-01e465f6cf91bc1419d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03du-0902000000-a582ea874eb4b3ef1f942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056s-1900000000-98ce9f789a4b6e24f3eb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-0519000000-5573debfe730dd31c7902016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-0912000000-e45000711e3acbc898492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r2-0900000000-7b38b7f078df24e2f1b12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0109000000-310d54adbeb85a5ad0e12021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rb-0924000000-611b2cdcafac098aaa422021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02bs-3900000000-8486c0729756571004242021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-1939e813c156479f231e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-1925000000-c5a6aa0ecaf96e1568582021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-1911000000-82ec7f3173c87c97d3fc2021-09-25View Spectrum
NMRNot Available
ChemSpider ID22912773
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5315600
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID469
DrugBank IDNot Available
HMDB IDHMDB30653
CRC / DFC (Dictionary of Food Compounds) IDCMK21-E:CMK21-E
EAFUS IDNot Available
Dr. Duke IDCRYPTOCHLOROGENIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029540
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 / Bioactivities
DescriptorIDDefinitionReference
hepatoprotective62868 Any compound that is able to prevent damage to the liver.CHEBI
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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).