trans-Caffeic acid (CHEM024665)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:50:51 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024665
Identification
Common Nametrans-Caffeic acid
ClassSmall Molecule
DescriptionCaffeic acid, also known as caffeate, 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. Caffeic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeic acid exists in all living species, ranging from bacteria to humans. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC9H8O4
Average Molecular Mass180.157 g/mol
Monoisotopic Mass180.042 g/mol
CAS Registry Number501-16-6
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeicacid
SMILESOC(=O)\C=C\C1=CC(O)=C(O)C=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP1.53ChemAxon
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9341000000-6dc8d392552b88bd4d8cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9351000000-50a6f144c73d7ab2794eSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-2793000000-251334452407128b38bdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9341000000-6dc8d392552b88bd4d8cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9351000000-50a6f144c73d7ab2794eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2793000000-251334452407128b38bdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0692000000-32624fa3a157a1f11cefSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0900000000-c3283a4b6f6f11b66cfbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b58Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-298c46c83441485d1d70Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9800000000-942c1934d3c7c395499eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-e9bdfc2dec7a449ccb11Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-b07143eccfcbf1caba0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-8f21d50b78f0d9fde98aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-4013461a961ebed6fd99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0019-2900000000-b41600c20a73cd258d40Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-8900000000-81ea3878c2912bdddf71Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-a1680074d0439bcd4c20Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-096221135a729c5d6aacSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0019-0900000000-98893b92962a162b2fb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03dr-2900000000-fc2581b0410dd8cb6e71Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-9200000000-0fd7b8f57372dc8172d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03dr-2900000000-454a31169c27631fb00cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-eb2466a330b617695c80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-31b407ecba8c8e813fd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-8f21d50b78f0d9fde98aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-4013461a961ebed6fd99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0019-2900000000-71ad48cc68ef0b7fe30dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-4d70eb21dfd5dcee3360Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-0900000000-eb4ac130dea5eced36c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0100-9800000000-68217b65b3cfbf177196Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-28ed8e427213908fdd9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0900000000-5913f01901b92071e2fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-090u-1900000000-2454d377d14f50d8c9b2Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-3c93f113512b8284301dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003501
FooDB IDFDB012666
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-8098
METLIN ID3316
PDB IDNot Available
Wikipedia LinkCaffeic acid
Chemspider ID1266077
ChEBI ID17395
PubChem Compound ID1549111
Kegg Compound IDC01481
YMDB IDYMDB01645
ECMDB IDM2MDB005541
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.
2. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8.
3. Kawaguchi H, Katsuyama Y, Danyao D, Kahar P, Nakamura-Tsuruta S, Teramura H, Wakai K, Yoshihara K, Minami H, Ogino C, Ohnishi Y, Kondo A: Caffeic acid production by simultaneous saccharification and fermentation of kraft pulp using recombinant Escherichia coli. Appl Microbiol Biotechnol. 2017 Jul;101(13):5279-5290. doi: 10.1007/s00253-017-8270-0. Epub 2017 Apr 10.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19812218
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19952409
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24088646
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24138287
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24206679