Record Information
Version1.0
Creation date2010-04-08 22:10:17 UTC
Update date2019-11-26 03:07:20 UTC
Primary IDFDB012662
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucocaffeic acid
DescriptionGlucocaffeic acid, also known as glucocaffeate, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Glucocaffeic acid is found, on average, in the highest concentration within a few different foods, such as highbush blueberries (Vaccinium corymbosum), jostaberries (Ribes × nidigrolaria), and gooseberries (Ribes uva-crispa) and in a lower concentration in blackcurrants (Ribes nigrum) and redcurrants (Ribes rubrum). Glucocaffeic acid has also been detected, but not quantified in, several different foods, such as black tea, robusta coffees (Coffea canephora), rubus (blackberry, raspberry), strawberries (Fragaria X ananassa), and red tea. This could make glucocaffeic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Glucocaffeic acid.
CAS Number17093-82-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility5.92 g/LALOGPS
logP-0.59ALOGPS
logP-0.74ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.17 m³·mol⁻¹ChemAxon
Polarizability32.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H18O9
IUPAC name(2E)-3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-3-1-7(5-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+
InChI KeyOHEYCHKLBCPRLZ-DUXPYHPUSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C(\C=C\C(O)=O)C=C2)C(O)C(O)C1O
Average Molecular Weight342.298
Monoisotopic Molecular Weight342.095082174
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Phenoxy compound
  • Styrene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGlucocaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01x0-6935000000-23334bdef41332ea934dSpectrum
Predicted GC-MSGlucocaffeic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-3503129000-0d88edd96503e6843575Spectrum
Predicted GC-MSGlucocaffeic acid, TBDMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucocaffeic acid, TBDMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucocaffeic acid, TBDMS_4_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucocaffeic acid, TBDMS_4_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucocaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucocaffeic acid, "Glucocaffeic acid,3TBDMS,#5" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01sl-0916000000-fece99020b1ba2f431ce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-3426b030fe1c2f3802162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900000000-453bcfd801322563f49d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2928000000-88b5911db1f82a296ebe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-d59fdc4b46b9803828a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u3-2900000000-66020d3549687cbf760d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-0293000000-79d8746a5db9047e63dc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-1490000000-92a6455fd6f33e2cf92b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-0900000000-6470eb3015c4debbcea92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0400-0906000000-c18c09fc539faa69158e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08ir-0934000000-a9a600a879e01c89c9ac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-2910000000-79bdaeeb30dfde578e482021-09-22View Spectrum
NMRNot Available
ChemSpider ID4823601
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6148082
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID488
DrugBank IDNot Available
HMDB IDHMDB34313
CRC / DFC (Dictionary of Food Compounds) IDCMK09-G:HJP66-C
EAFUS IDNot Available
Dr. Duke IDLINOCAFFEIN
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
Processing...
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).