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Record Information
Version3.6
Creation Date2006-05-22 14:17:29 UTC
Update Date2014-06-16 20:25:56 UTC
HMDB IDHMDB01964
Secondary Accession NumbersNone
Metabolite Identification
Common NameCaffeic acid
DescriptionCaffeic acid 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 ).
Structure
Thumb
Synonyms
  1. 3,4-Dihydroxybenzeneacrylate
  2. 3,4-Dihydroxybenzeneacrylic acid
  3. 3,4-Dihydroxycinnamate
  4. 3,4-Dihydroxycinnamic acid
  5. Caffeate
  6. Caffeic acid pure
  7. Caffeicacid
  8. cis-Caffeate
  9. cis-Caffeic acid
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Namecis-caffeic acid
CAS Registry Number331-39-5
SMILES
OC(=O)\C=C/C1=CC=C(O)C(O)=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-RQOWECAXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassCinnamic Acid Derivatives
Sub ClassHydroxycinnamic Acid Derivatives
Other Descriptors
  • Caffeate derivatives(KEGG)
  • Cinnamic Acid Derivatives
  • Coumaric Acid Derivatives
  • Organic Compounds
  • caffeic acid(ChEBI)
Substituents
  • 1,2 Diphenol
  • Allyl Alcohol
  • Carboxylic Acid
  • Enone
  • Phenol
  • Phenol Derivative
  • Phenylpropene
  • Styrene
Direct ParentHydroxycinnamic Acid Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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)3.14ChemAxon
pKa (strongest basic)-6.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area77.76ChemAxon
rotatable bond count2ChemAxon
refractivity47.02ChemAxon
polarizability17.13ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Platelet
  • Prostate
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 +/- 0.000 uMAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 457
  • Not Applicable
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 Quantified0.382 +/- 0.065 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID457
FoodDB IDFDB002558
KNApSAcK IDNot Available
Chemspider ID1266077
KEGG Compound IDC01481
BioCyc IDCAFFEATE
BiGG IDNot Available
Wikipedia LinkCaffeic_acid
NuGOwiki LinkHMDB01964
Metagene LinkHMDB01964
METLIN ID3316
PubChem Compound1549111
PDB IDNot Available
ChEBI ID17395
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. Nippon 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

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