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Showing Compound trans-Caffeic acid (FDB002559)

Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2019-11-26 02:57:37 UTC
Primary IDFDB002559
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-Caffeic acid
Description3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms.
CAS Number501-16-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,4-Dihydroxy-trans-cinnamateChEBI
3,4-Dihydroxycinnamic acidChEBI
trans-CaffeateChEBI
3,4-Dihydroxy-trans-cinnamic acidGenerator
3,4-DihydroxycinnamateGenerator
CaffeateGenerator
Caffeic acid, monosodium saltHMDB
Caffeic acid, (e)-isomerHMDB
Sodium caffeateHMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3,4-Dihydroxycinnamic acidHMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acidHMDB
(e)-Caffeic acidHMDB
3,4-Dihydroxybenzeneacrylic 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
trans-3,4-Dihydroxycinnamic acidHMDB
Caffeic acidHMDB
3',4'-Dihydroxycinnamic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;HMDB
(2E)-3-(3,4-dihydroxyphenyl)acrylic acidbiospider
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acidbiospider
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acidbiospider
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-biospider
trans-Caffeic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.67ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.64ChemAxon
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
Polarizability17.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O4
IUPAC name(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
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 stateSolid
Physical DescriptionNot Available
Mass CompositionC 60.00%; H 4.48%; O 35.52%DFC
Melting PointMp 223-225° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.35
Experimental pKapKa2 9.07 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCaffeic acid, 3 TMS, GC-MS Spectrumsplash10-014i-1593000000-b24e97b50ed1f50252f3Spectrum
GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-001i-9800000000-bae43e98e22babcbf5a7Spectrum
GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9600000000-6140146b8e32bda5e3c9Spectrum
GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0593000000-16610dfa8ac4ac67a4c2Spectrum
GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1593000000-b24e97b50ed1f50252f3Spectrum
GC-MSCaffeic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0592000000-1bb03bc99be6718d247eSpectrum
Predicted GC-MSCaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1900000000-6a963e50b910f05b6825Spectrum
Predicted GC-MSCaffeic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b58Spectrum
Predicted GC-MSCaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-90ad608487db4c1124692021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-dcc07d9a43defb5683a02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-762c7a39be8e2819bc512021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0019-4900000000-e716811ee5cf56acce9e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-037f59c6ff1daadca2a02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0019-6900000000-a67fe3c28be25c2fa72b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0019-1900000000-62d755ec157c381054b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6c93facd0d3caabc67f12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001r-0900000000-7b2d4553b6a25b853d4b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-3ed879b5217c5d703cd52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-bddc5a2872c93f7185ba2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-9600000000-376ae5146fc0f93c9ff52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-7d707e3512f8df7d6c532021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-c904417e68f103c0c9632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-f31bbdf32d6b72a381e72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-ad7b879926d9c809f9c82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014s-1900000000-d3c79213f8f23833fadc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-3adb4dbfdaeb614b61e62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-8f7413c3605b295159312021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-467621cde3e4486ad6bf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-7fdae010c3ffe7ab11562021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-9000000000-a67e2178525a89f45da92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-8407d64b83bf427de33f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03dr-0900000000-91200c128446226f6ecb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-2ec4b8c30dbd96e112282021-09-20View Spectrum
NMRNot Available
ChemSpider ID600426
ChEMBL IDCHEMBL145
KEGG Compound IDC01481
Pubchem Compound ID689043
Pubchem Substance IDNot Available
ChEBI ID16433
Phenol-Explorer ID497
DrugBank IDDB01880
HMDB IDHMDB03501
CRC / DFC (Dictionary of Food Compounds) IDCMK09-G:CMK10-A
EAFUS IDNot Available
Dr. Duke IDTRANS-CAFFEIC-ACID
BIGG ID37057
KNApSAcK IDC00000615
HET IDDHC
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).