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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:07:26 UTC
Update Date2022-03-07 02:54:03 UTC
HMDB IDHMDB0034313
Secondary Accession Numbers
  • HMDB34313
Metabolite Identification
Common 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 herbal tea, fats and oils, robusta coffees (Coffea canephora), green tea, and strawberries (Fragaria X ananassa). 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.
Structure
Thumb
Synonyms
ValueSource
GlucocaffeateGenerator
Caffeic acid 4-O-glucosideHMDB
LinocaffeinHMDB
(2E)-3-(3-Hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoateGenerator
Chemical FormulaC15H18O9
Average Molecular Weight342.298
Monoisotopic Molecular Weight342.095082174
IUPAC Name(2E)-3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
Traditional Name(2E)-3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
CAS Registry Number17093-82-2
SMILES
OCC1OC(OC2=C(O)C=C(\C=C\C(O)=O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility166000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID488
FooDB IDFDB012662
KNApSAcK IDNot Available
Chemspider ID4823601
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6148082
PDB IDNot Available
ChEBI ID143038
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1841871
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .