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Record Information
Version3.6
Creation Date2006-08-24 09:23:35 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04811
Secondary Accession NumbersNone
Metabolite Identification
Common Name2,4-Dichlorophenol
Description2,4-Dichlorophenol is a chlorinated organic chemical due to environmental exposure, that can be detected in breast milk. The free species of phenols and chlorinated organic appear to be most prevalent in milk. (PMID 16377264 ).
Structure
Thumb
Synonyms
ValueSource
24-DichlorophenolChEMBL
1,3-dichloro-4-HydroxybenzeneHMDB
2,4-dichloro-PhenolHMDB
2,4-DichlorophenateHMDB
2,4-Dichlorophenic acidHMDB
4,6-DichlorophenolHMDB
Chemical FormulaC6H4Cl2O
Average Molecular Weight163.001
Monoisotopic Molecular Weight161.963920164
IUPAC Name2,4-dichlorophenol
Traditional Name2,4-dichlorophenol
CAS Registry Number120-83-2
SMILES
OC1=CC=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
InChI KeyInChIKey=HFZWRUODUSTPEG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentP-chlorophenols
Alternative Parents
Substituents
  • 4-chlorophenol
  • 2-chlorophenol
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.5 mg/mL at 20 °CNot Available
LogP3.06HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.49 mg/mLALOGPS
logP3.14ALOGPS
logP2.88ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.44ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.65 m3·mol-1ChemAxon
Polarizability14.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-f54ce3be94c6da8704e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9500000000-d8e24612e2f3f051febfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-95735b217c7349767bf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-9600000000-4fa477756aa23b7adcc6View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-7900000000-cb2b5b10e5e1f6220386View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.00151(0.00128-0.00299) umol/mmol creatinineNot AvailableBothNormal
    • Report on Human B...
details
UrineDetected and Quantified0.00212(0.00124-0.00401) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Report on Human B...
details
UrineDetected and Quantified0.0008 (0.0007-0.00088) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000465 (0.000430-0.000506) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • 12031833
    • Report on Human B...
    • National Health a...
details
UrineDetected and Quantified0.000714 (0.000520-0.00101) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • 12031833
    • Report on Human B...
    • National Health a...
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 IDNot Available
FoodDB IDFDB023422
KNApSAcK IDNot Available
Chemspider ID8140
KEGG Compound IDC02625
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04811
Metagene LinkHMDB04811
METLIN ID7075
PubChem Compound8449
PDB IDNot Available
ChEBI ID16738
References
Synthesis ReferenceZiegler, Erich; Simmler, Inge. Acid condensation of 2,4-dichlorophenol with trioxymethylene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1941), 74B 1871-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Crespin MA, Gallego M, Valcarcel M: Solid-phase extraction method for the determination of free and conjugated phenol compounds in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jun 25;773(2):89-96. [12031833 ]
  2. Ye X, Kuklenyik Z, Needham LL, Calafat AM: Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):110-5. Epub 2005 Dec 27. [16377264 ]