Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2019-11-26 03:07:20 UTC
Primary IDFDB012666
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-Caffeic acid
Descriptioncis-Caffeic acid, also known as caffeate or DHCA, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. cis-Caffeic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). cis-Caffeic acid exists in all living species, ranging from bacteria to humans. cis-Caffeic acid has been detected, but not quantified in, fats and oils and nuts. This could make cis-caffeic acid a potential biomarker for the consumption of these foods. cis-Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
CAS Number4361-87-9
Structure
Thumb
Synonyms
SynonymSource
3,4-Dihydroxycinnamic acidChEBI
CaffeateChEBI
Caffeic acidChEBI
3,4-DihydroxycinnamateGenerator
cis-CaffeateGenerator
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
Caffeic acid pureHMDB
CaffeicacidHMDB
(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-Caffeic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
Isocaffeic acidHMDB
cis-3,4-Dihydroxycinnamic acidHMDB
cis-Caffeic acidHMDB
Predicted PropertiesNot Available
Chemical FormulaC9H8O4
IUPAC name
InChI IdentifierInChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChI KeyQAIPRVGONGVQAS-DUXPYHPUSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC(O)=C(O)C=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.00%; H 4.48%; O 35.52%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-MSNot Available
MS/MSNot Available
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 ID497
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMK09-G:HJP76-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