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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-24 09:23:35 UTC
Update Date2020-10-09 21:09:12 UTC
HMDB IDHMDB0004811
Secondary Accession Numbers
  • HMDB04811
Metabolite Identification
Common Name2,4-Dichlorophenol
Description2,4-Dichlorophenol belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. 2,4-Dichlorophenol exists in all living species, ranging from bacteria to plants to humans. 2,4-Dichlorophenol has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2,4-dichlorophenol a potential biomarker for the consumption of these foods. 2,4-Dichlorophenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2,4-Dichlorophenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on 2,4-Dichlorophenol.
Structure
Data?1582752313
Synonyms
ValueSource
2,4-Dichlorophenol potassiumMeSH
2,4-Dichlorophenol, 14C-labeled CPDMeSH
2,4-Dichlorophenol sodiumMeSH
4,6-DichlorophenolMeSH
24-DichlorophenolChEMBL, HMDB
1,3-dichloro-4-HydroxybenzeneHMDB
2,4-dichloro-PhenolHMDB
2,4-DichlorophenateHMDB
2,4-Dichlorophenic acidHMDB
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 KeyHFZWRUODUSTPEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 4-chlorophenol
  • 2-chlorophenol
  • 2-halophenol
  • 4-halophenol
  • 1,3-dichlorobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Molecular 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 Molecular Properties
PropertyValueSource
Water Solubility2.49 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.65 m³·mol⁻¹ChemAxon
Polarizability14.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
2,4-Dichlorophenol,1TMS,#11381.496https://arxiv.org/abs/1905.12712
2,4-Dichlorophenol,1TBDMS,#11619.5958https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-4fa477756aa23b7adcc62017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-4fa477756aa23b7adcc62018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2900000000-381e64530360900216082016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9740000000-cebcdb789d84c6207e032017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-7900000000-cb2b5b10e5e1f62203862014-09-20View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-f54ce3be94c6da8704e52012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9500000000-d8e24612e2f3f051febf2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-95735b217c7349767bf62012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-9600000000-4fa477756aa23b7adcc62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-94ffb74b937db7fcfcaa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-9300000000-ee63363c23d6239dcef62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0229-0900000000-4d6568956b7f0b03bf642021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9200000000-06071826a250ba5266142021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-001i-9100000000-7d698141859118d007732021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9500000000-e35d2e99fffd2ed1cb3b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-62d63d30b88cc774b3782021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-001i-9100000000-728df1b61fb336defed02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-001i-9100000000-a07532c1fc37fb84219b2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-3ca52610ea3d011485752016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-50870879fea8dd32af552016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-0900000000-74b84ace3e15b790e6912016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ed1f169a0b551f0c1b322016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-ed1f169a0b551f0c1b322016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-6781704e02cfe0c0c2eb2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-af0cce6f474d61a226eb2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-7e8f9cda7f51674737472021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gi-5900000000-0b992a2c78f70c4234f82021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-a60be7ecf78d14d05b402021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-b371a1d677048c71ce522021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9300000000-efc7672a22c497bd5fe92021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, benzene, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, benzene, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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
    • National Health a...
    • Report on Human B...
details
UrineDetected and Quantified0.000714 (0.000520-0.00101) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • 12031833
    • National Health a...
    • Report on Human B...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023422
KNApSAcK IDNot Available
Chemspider ID8140
KEGG Compound IDC02625
BioCyc ID24-DICHLOROPHENOL
BiGG IDNot Available
Wikipedia Link2,4-Dichlorophenol
METLIN ID7075
PubChem Compound8449
PDB IDNot Available
ChEBI ID16738
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029789
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. [PubMed: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. [PubMed:16377264 ]