Record Information
Version1.0
Creation date2018-05-02 12:09:31 UTC
Update date2018-05-04 14:25:18 UTC
FoodComEx IDPC001180
FoodDB RecordFDB002582
Chemical Information
NameChlorogenic acid
DescriptionChlorogenic acid, also known as chlorogenate or 3-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. Chlorogenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chlorogenic acid has been detected, but not quantified in, several different foods, such as limes, cocoa beans, celery leaves, caraway, and epazotes. This could make chlorogenic acid a potential biomarker for the consumption of these foods.
CAS Number327-97-9
Structure
Thumb
Synonyms
SynonymSource
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidGenerator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidChEBI
[1S-(1α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylateGenerator
[1S-(1α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidGenerator
3-(3,4-Dihydroxycinnamoyl)quinateGenerator
3-(3,4-Dihydroxycinnamoyl)quinic aciddb_source
3-CaffeoylquinateGenerator
3-Caffeoylquinic acidmanual
3-O-CaffeoylquinateGenerator
3-O-Caffeoylquinic acidChEBI
3-trans-Caffeoylquinic acidHMDB
5-Caffeoylquinic acid?manual
5-O-(3,4-Dihydroxycinnamoyl)-L-quinateGenerator
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acidChEBI
5-O-Caffeoylquinic acid?manual
Caffeoyl quinateGenerator
Caffeoyl quinic acidChEBI
Caffetannic aciddb_source
ChlorogenateChEBI
Chlorogenic aciddb_source
Helianthic aciddb_source
HeriguardHMDB
HlorogenateHMDB
Hlorogenic acidHMDB
trans-5-O-Caffeoyl-D-quinateChEBI
trans-5-O-Caffeoyl-D-quinic acidGenerator
Chemical FormulaC16H18O9
IUPAC name(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
InChI IdentifierInChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
InChI KeyCWVRJTMFETXNAD-JUHZACGLSA-N
Isomeric SMILESO[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O
Average Molecular Weight354.3087
Monoisotopic Molecular Weight354.095082174
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage Conditions-18°C
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
AKSci E748
AKSci J10338
AKSci J40040
AKSci O675
Cayman Chemical 70930
Glentham GE3686
MetaSci HMDB0003164
Sigma-Aldrich HMDB0003164
Toronto Research Chemicals C366540