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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2019-06-14 20:59:13 UTC
HMDB IDHMDB0001964
Secondary Accession Numbers
  • HMDB01964
Metabolite Identification
Common NameCaffeic acid
DescriptionCaffeic acid (CAS: 331-39-5) 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 ). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925 ).
Structure
Data?1560545953
Synonyms
ValueSource
3,4-Dihydroxy-trans-cinnamateChEBI
3,4-Dihydroxycinnamic acidChEBI
CAFFEIC ACIDChEBI
trans-CaffeateChEBI
3,4-Dihydroxy-trans-cinnamic acidGenerator
3,4-DihydroxycinnamateGenerator
CAFFEateGenerator
trans-Caffeic acidGenerator
Caffeic acid, monosodium saltMeSH
Caffeic acid, (e)-isomerMeSH
Sodium caffeateMeSH
(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
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeic acid
CAS Registry Number501-16-6
SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.15SANGSTER (1993)
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1593000000-b24e97b50ed1f50252f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9800000000-bae43e98e22babcbf5a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9600000000-6140146b8e32bda5e3c9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0593000000-16610dfa8ac4ac67a4c2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1593000000-b24e97b50ed1f50252f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0592000000-1bb03bc99be6718d247eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-6a963e50b910f05b6825JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b58JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-f31bbdf32d6b72a381e7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-3f202efcd71f15f33da9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-1900000000-c772ffdf277b1e52c37aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdr-9700000000-5a4b1d97b748046bf13aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f196cd5c6ab6f34ffec7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-359be86d681a33921515JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0913-2900000000-8a1b926d906ffae34e16JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Platelet
  • Prostate
  • Stratum Corneum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.12 +/- 1.547 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.943 +/- 1.055 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.915 +/- 1.695 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.702 +/- 0.223 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.366 +/- 0.088 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.241 +/- 0.041 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.428 +/- 0.147 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.434 +/- 2.174 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.033 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0-18.887 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected and Quantified11.268 +/- 1.388 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.490 +/- 3.663 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.545 +/- 1.665 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified11.823 +/- 1.776 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified14.987 +/- 13.322 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457 details
UrineDetected and Quantified3.5 (1.2-22.9) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.1 (0.1-6.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.6 (1.2-4.1) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.16 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.41 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0065 +/- 0.013 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.019 +/- 0.032 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.046 +/- 0.019 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.026 +/- 0.026 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.13 +/- 0.032 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.026 +/- 0.013 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.013 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.620 +/- 0.240 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.760 +/- 0.567 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.317 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0460-1.410 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.382 +/- 0.065 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01880
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000615
Chemspider IDNot Available
KEGG Compound IDC01481
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCaffeic_acid
METLIN IDNot Available
PubChem Compound689043
PDB IDNot Available
ChEBI ID16433
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
  3. Saija A, Tomaino A, Trombetta D, De Pasquale A, Uccella N, Barbuzzi T, Paolino D, Bonina F: In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents. Int J Pharm. 2000 Apr 10;199(1):39-47. [PubMed:10794925 ]
  4. Gonthier MP, Verny MA, Besson C, Remesy C, Scalbert A: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J Nutr. 2003 Jun;133(6):1853-9. [PubMed:12771329 ]
  5. Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, Scalbert A: Chlorogenic acid is absorbed in its intact form in the stomach of rats. J Nutr. 2006 May;136(5):1192-7. [PubMed:16614403 ]
  6. Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. [PubMed:12207832 ]
  7. Uno J, Tanaka R, Branchini ML, Aoki FH, Yarita K, Sano A, Fukushima K, Mikami Y, Nishimura K, Miyaji M: Atypical Cryptococcus neoformans isolate from an HIV-infected patient in Brazil. Nihon Ishinkin Gakkai Zasshi. 2001;42(3):127-32. [PubMed:11479533 ]
  8. Verma RP: A classical QSAR study on some platelet aggregation inhibitors. Mini Rev Med Chem. 2006 Apr;6(4):467-82. [PubMed:16613584 ]
  9. Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. [PubMed:15866491 ]
  10. Olthof MR, Hollman PC, Katan MB: Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001 Jan;131(1):66-71. [PubMed:11208940 ]
  11. 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. [PubMed:16870009 ]
  12. 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. [PubMed:28396925 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595