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4-Methylcatechol

PubChem CID
9958
Structure
4-Methylcatechol_small.png
4-Methylcatechol_3D_Structure.png
Molecular Formula
Synonyms
  • 4-Methylcatechol
  • 452-86-8
  • 4-methylbenzene-1,2-diol
  • 3,4-Dihydroxytoluene
  • Homocatechol
Molecular Weight
124.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
4-methylcatechol is a methylcatechol having a single methyl substituent at the 4-position. It has been isolated from Picea abies. It has a role as a hapten, a carcinogenic agent, an antioxidant, a human metabolite and a plant metabolite.
4-Methylcatechol has been reported in Camellia sinensis, Geosmithia langdonii, and Bistorta manshuriensis with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Methylcatechol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-methylbenzene-1,2-diol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ZBCATMYQYDCTIZ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=CC(=C(C=C1)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C7H8O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3,4-dihydroxytoluene
  • 4-methylcatechol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
124.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
124.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
124.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
40.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
9
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
92.9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

White or light brown solid; [Alfa Aesar MSDS]
Solid

3.2.2 Boiling Point

251 °C
PhysProp

3.2.3 Melting Point

65 °C
PhysProp
65 °C

3.2.4 Vapor Pressure

0.0028 [mmHg]

3.2.5 LogP

1.37
HANSCH,C ET AL. (1995)
1.37
HANSCH,C ET AL. (1995)

3.2.6 Ionization Efficiency

Ionization mode
Positive
logIE
-0.28
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)

3.2.7 Dissociation Constants

3.2.8 Collision Cross Section

121 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
121.5 Ų [M-H]-
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.2.9 Kovats Retention Index

Standard non-polar
1246.1
Semi-standard non-polar
1295.1 , 1293.6 , 1293 , 1293.4 , 1294
Standard polar
2727

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Phenols

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
600 MHz
Solvent
Water
pH
7.02
Shifts [ppm]:Intensity
6.68:9.72, 6.78:20.78, 2.21:100.00, 6.67:8.44, 6.68:9.19, 6.68:10.55, 6.82:33.66, 6.67:9.19, 6.67:8.49, 6.67:7.37, 6.78:20.20, 6.67:7.74, 6.83:28.44, 6.68:11.41, 6.68:10.72
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2 of 3
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Instrument Name
Varian A-60
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
6.82:118.85:0.36, 2.21:22.24:1.00, 6.78:119.56:0.91, 6.67:123.72:0.37
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 9
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

268.0 100

180.0 62.86

149.0 58.16

179.0 54.65

165.0 48.05

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Notes
instrument=Leco Pegasus IV
2 of 9
View All
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Leco Pegasus IV
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

268 100

180 62.86

149 58.16

179 54.65

165 48.05

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4.3.2 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

107.031 100

125.005 55.09

79.111 18.63

77.135 4.66

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 7
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

65.00242 100

49.00875 78.50

122.03631 48.50

41.0031 19.60

108.0192 4.90

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4.3.3 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
123.0451535
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
negative
Collision Energy
HCD (NCE 20-30-40%)
Top 5 Peaks

123.0451 100

122.03731 7.90

108.02173 3.70

105.03464 1.10

95.05029 0.70

Thumbnail
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2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
125.0597055
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
positive
Collision Energy
HCD (NCE 20-30-40%)
Top 5 Peaks

69.06998 100

97.06485 59

79.05425 24.70

67.05443 4.90

125.05978 4.70

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4.3.4 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
123.045
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

122.038887 100

108.021744 23.88

108.024673 21.68

123.045311 16.28

123.048439 14.29

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
123.045
Instrument
Orbitrap
Ionization Mode
negative
Top 5 Peaks

123.043884 100

124.047256 6.91

95.012436 5.84

66.996376 3.35

134.925171 3.14

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4.4 UV Spectra

4.4.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 IR Spectra

4.5.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Melt
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
M34200
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.5.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
M34200
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
M34200
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Antioxidants
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)
Carcinogens
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)
Neuroprotective Agents
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

9.2 Metabolism / Metabolites

4-methyl-hydroquinone is a known human metabolite of 4-Methylphenol.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

9.3 Biochemical Reactions

9.4 Transformations

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (11.9%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (10.2%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (98.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 59 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (11.9%)

Acute Tox. 4 (10.2%)

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (98.3%)

10.1.3 Hazards Summary

A skin and strong eye irritant; Harmful by inhalation; Toxic by ingestion and skin absorption; [Alfa Aesar MSDS] See Catechol.

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
4-Methylcatechol: Does not have an individual approval but may be used under an appropriate group standard

11 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Smoking
References

PubMed: 9137998, 8294547, 10636262, 6890513, 12194923, 15649624, 19222926, 15878312, 18666198, 18029489, 19036546

Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 ChEMBL Target Tree

17.5 UN GHS Classification

17.6 NORMAN Suspect List Exchange Classification

17.7 CCSBase Classification

17.8 EPA DSSTox Classification

17.9 LOTUS Tree

17.10 EPA Substance Registry Services Tree

17.11 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
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    https://echa.europa.eu/web/guest/legal-notice
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  9. New Zealand Environmental Protection Authority (EPA)
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    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  10. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  11. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    4-Methylcatechol
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  12. ChEBI
  13. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  14. ChEMBL
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  15. ClinicalTrials.gov
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  16. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  17. FooDB
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    https://foodb.ca/about
    4-Methyl-1,2-benzenediol
    https://foodb.ca/compounds/FDB008861
  18. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    https://haz-map.com/About
  19. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. NIST Mass Spectrometry Data Center
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    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    1,2-Benzenediol, 4-methyl-
    http://www.nist.gov/srd/nist1a.cfm
  21. SpectraBase
  22. IUPAC Digitized pKa Dataset
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. KEGG
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    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  25. KNApSAcK Species-Metabolite Database
  26. Natural Product Activity and Species Source (NPASS)
  27. West Coast Metabolomics Center-UC Davis
    Methylcatechol
  28. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    4-methylcatechol
  29. Metabolomics Workbench
  30. NMRShiftDB
  31. Protein Data Bank in Europe (PDBe)
  32. RCSB Protein Data Bank (RCSB PDB)
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  36. Thieme Chemistry
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  42. GHS Classification (UNECE)
  43. EPA Substance Registry Services
  44. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  45. PATENTSCOPE (WIPO)
  46. NCBI
CONTENTS