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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:16 UTC

HMDB ID

HMDB0000873

Secondary Accession Numbers

HMDB00873

Metabolite Identification

Common Name

4-Methylcatechol

Description

4-Methylcatechol, also known as homocatechol or toluene-3,4-diol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Outside of the human body, 4-Methylcatechol is found, on average, in the highest concentration within a few different foods such as coffee and cocoa powders and in a lower concentration in beers. 4-Methylcatechol has also been detected, but not quantified in eggplants. This could make 4-methylcatechol a potential biomarker for the consumption of these foods. Recent studies have suggested that a lack of brain-derived neurotrophic factor (BDNF) in the limbic system may cause neuropathic pain (PMID:22198556 ). It is both a substrate and a suicide inhibitor of catechol 2,3-dioxygenase (PMID:15006807 ). 4-Methylcatechol is a metabolite of homoprotocatechuic acid (PMID:4974346 ). 4-Methylcatechol is known to induce the production of BDNF.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dihydroxy-4-methylbenzene	ChEBI
2-Hydroxy-4-methylphenol	ChEBI
3,4-Dihydroxytoluene	ChEBI
4-Methyl-1,2-benzenediol	ChEBI
4-Methyl-1,2-dihydroxybenzene	ChEBI
4-Methylpyrocatechol	ChEBI
Homocatechol	ChEBI
Homopyrocatechol	ChEBI
p-Methylcatechol	ChEBI
p-Methylpyrocatechol	ChEBI
Toluene-3,4-diol	ChEBI
1-Methyl-3,4-dihydroxybenzene	HMDB
4-Methyl-pyrocatechol	HMDB
4-Methylcatehol	HMDB
4-Metylcatechol	HMDB
5-Methylcatechol	HMDB

Chemical Formula

C₇H₈O₂

Average Molecular Weight

124.1372

Monoisotopic Molecular Weight

124.0524295

IUPAC Name

4-methylbenzene-1,2-diol

Traditional Name

4-methyl-1,2-benzenediol

CAS Registry Number

452-86-8

SMILES

CC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3

InChI Key

ZBCATMYQYDCTIZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

P-cresol
M-cresol
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methylcatechol (CHEBI:17254 )
a catechol (4-METHYLCATECHOL )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	65 °C	Not Available
Boiling Point	247.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	24900 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.37	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	121.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002102

Predicted Molecular Properties

Property	Value	Source
Water Solubility	37.9 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.88	ChemAxon
logS	-0.52	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.06 m³·mol⁻¹	ChemAxon
Polarizability	12.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.969	31661259
DarkChem	[M-H]-	122.575	31661259
AllCCS	[M+H]+	124.257	32859911
AllCCS	[M-H]-	121.587	32859911
DeepCCS	[M+H]+	124.328	30932474
DeepCCS	[M-H]-	120.496	30932474
DeepCCS	[M-2H]-	157.79	30932474
DeepCCS	[M+Na]+	133.33	30932474
AllCCS	[M+H]+	124.3	32859911
AllCCS	[M+H-H2O]+	119.4	32859911
AllCCS	[M+NH4]+	128.8	32859911
AllCCS	[M+Na]+	130.1	32859911
AllCCS	[M-H]-	121.6	32859911
AllCCS	[M+Na-2H]-	123.6	32859911
AllCCS	[M+HCOO]-	125.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylcatechol	CC1=CC=C(O)C(O)=C1	2692.8	Standard polar	33892256
4-Methylcatechol	CC1=CC=C(O)C(O)=C1	1137.4	Standard non polar	33892256
4-Methylcatechol	CC1=CC=C(O)C(O)=C1	1279.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methylcatechol,1TMS,isomer #1	CC1=CC=C(O[Si](C)(C)C)C(O)=C1	1294.6	Semi standard non polar	33892256
4-Methylcatechol,1TMS,isomer #2	CC1=CC=C(O)C(O[Si](C)(C)C)=C1	1288.2	Semi standard non polar	33892256
4-Methylcatechol,2TMS,isomer #1	CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1366.3	Semi standard non polar	33892256
4-Methylcatechol,1TBDMS,isomer #1	CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	1539.6	Semi standard non polar	33892256
4-Methylcatechol,1TBDMS,isomer #2	CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	1529.2	Semi standard non polar	33892256
4-Methylcatechol,2TBDMS,isomer #1	CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	1851.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Methylcatechol GC-EI-TOF (Non-derivatized)	splash10-014i-1930000000-6225053efa0739efca3d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methylcatechol GC-EI-TOF (Non-derivatized)	splash10-014i-1930000000-6225053efa0739efca3d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-2d8d69f64905f6f9396e	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (2 TMS) - 70eV, Positive	splash10-0udj-3940000000-d5331c4c752130a85084	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a6r-1900000000-9045a710867168d6cc51	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004i-9000000000-0e20b47a091c0b3e39ab	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-004i-9000000000-0e20b47a091c0b3e39ab	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol , negative-QTOF	splash10-00di-0900000000-7db9fcc9e56ad8a39080	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 40V, Negative-QTOF	splash10-014j-9200000000-f6f538341319fcc5433b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOF	splash10-00di-0900000000-97cd131a887e2f870186	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 10V, Positive-QTOF	splash10-014i-9000000000-6981a2924f054e884c5c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 35V, Negative-QTOF	splash10-00di-0900000000-0aaf237b7039ed11a1d7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 40V, Positive-QTOF	splash10-0553-9000000000-fe5754c269058c591feb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 20V, Positive-QTOF	splash10-0006-9000000000-c1c0f17738a12823f96d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOF	splash10-00di-2900000000-e5f3b6d9329514c202a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOF	splash10-00di-1900000000-d5abc716689493ede24f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOF	splash10-00di-0900000000-6bd82a87c9fe3a5ac3f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Methylcatechol 40V, Negative-QTOF	splash10-03dj-9000000000-5833215eaa6163ad44f4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Positive-QTOF	splash10-004i-0900000000-efa52ff0e22aa918c832	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Positive-QTOF	splash10-004i-2900000000-1813508ce877db8f3b51	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 40V, Positive-QTOF	splash10-0v00-9200000000-42f7207a63d63607822f	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOF	splash10-00di-0900000000-965e88496dc55d1d3a08	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOF	splash10-00di-1900000000-528bea85898c5bbee974	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 40V, Negative-QTOF	splash10-05fu-9400000000-25d222489152bbee4894	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Positive-QTOF	splash10-056r-2900000000-f83a6dc29f504d8a27ea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Positive-QTOF	splash10-004i-9400000000-f09039303c5f740d5e99	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 40V, Positive-QTOF	splash10-0gdi-9000000000-5a1ebbe40df7d21e329f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOF	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOF	splash10-00di-2900000000-5af433d114ee67df4fda	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected and Quantified	7.814 +/- 1.128 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	14.339 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Urine	Detected and Quantified	1.8 +/- 1.2 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	6890513	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	3.6 +/- 1.5 umol/mmol creatinine	Adult (>18 years old)	Male	Smoking	6890513	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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 ]
Smoking
Carmella SG, La Voie EJ, Hecht SS: Quantitative analysis of catechol and 4-methylcatechol in human urine. Food Chem Toxicol. 1982 Oct;20(5):587-90. [PubMed:6890513 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB04120

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Methylcatechol

METLIN ID

5834

PubChem Compound

9958

PDB ID

Not Available

ChEBI ID

17254

Food Biomarker Ontology

Not Available

VMH ID

4MCAT

MarkerDB ID

Not Available

Good Scents ID

rw1205021

References

Synthesis Reference

Liang, Zesheng; Zhang, Ying; Wu, Baojun; Zhang, Mingsen; Wang, Xiu'en. Preparation of 4-methylcatechol with good yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 6 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Baba S, Furuta T, Horie M, Nakagawa H: Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans. J Pharm Sci. 1981 Jul;70(7):780-2. [PubMed:7264927 ]
Alanko J, Riutta A, Holm P, Mucha I, Vapaatalo H, Metsa-Ketela T: Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties. Free Radic Biol Med. 1999 Jan;26(1-2):193-201. [PubMed:9890654 ]
Carmella SG, La Voie EJ, Hecht SS: Quantitative analysis of catechol and 4-methylcatechol in human urine. Food Chem Toxicol. 1982 Oct;20(5):587-90. [PubMed:6890513 ]
Glasser G, Graefe EU, Struck F, Veit M, Gebhardt R: Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine. 2002 Jan;9(1):33-40. [PubMed:11924762 ]
Ridder L, Briganti F, Boersma MG, Boeren S, Vis EH, Scozzafava A, Veeger C, Rietjens IM: Quantitative structure/activity relationship for the rate of conversion of C4-substituted catechols by catechol-1,2-dioxygenase from Pseudomonas putida (arvilla) C1. Eur J Biochem. 1998 Oct 1;257(1):92-100. [PubMed:9799107 ]
Capasso R, Evidente A, Schivo L, Orru G, Marcialis MA, Cristinzio G: Antibacterial polyphenols from olive oil mill waste waters. J Appl Bacteriol. 1995 Oct;79(4):393-8. [PubMed:7592132 ]
Okuta A, Ohnishi K, Harayama S: Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol. Appl Environ Microbiol. 2004 Mar;70(3):1804-10. [PubMed:15006807 ]
Shen Y: In vitro cytotoxicity of BTEX metabolites in HeLa cells. Arch Environ Contam Toxicol. 1998 Apr;34(3):229-34. [PubMed:9504968 ]
Graefe EU, Veit M: Urinary metabolites of flavonoids and hydroxycinnamic acids in humans after application of a crude extract from Equisetum arvense. Phytomedicine. 1999 Oct;6(4):239-46. [PubMed:10589442 ]
Fukuhara K, Ishikawa K, Yasuda S, Kishishita Y, Kim HK, Kakeda T, Yamamoto M, Norii T, Ishikawa T: Intracerebroventricular 4-methylcatechol (4-MC) ameliorates chronic pain associated with depression-like behavior via induction of brain-derived neurotrophic factor (BDNF). Cell Mol Neurobiol. 2012 Aug;32(6):971-7. doi: 10.1007/s10571-011-9782-2. Epub 2011 Dec 25. [PubMed:22198556 ]
Scheline RR: Drug metabolism by intestinal microorganisms. J Pharm Sci. 1968 Dec;57(12):2021-37. doi: 10.1002/jps.2600571202. [PubMed:4974346 ]

Showing metabocard for 4-Methylcatechol (HMDB0000873)

MOL for HMDB0000873 (4-Methylcatechol)

3D MOL for HMDB0000873 (4-Methylcatechol)

3D SDF for HMDB0000873 (4-Methylcatechol)

3D-SDF for HMDB0000873 (4-Methylcatechol)

PDB for HMDB0000873 (4-Methylcatechol)

3D PDB for HMDB0000873 (4-Methylcatechol)

SMILES for HMDB0000873 (4-Methylcatechol)

INCHI for HMDB0000873 (4-Methylcatechol)

Structure for HMDB0000873 (4-Methylcatechol)

3D Structure for HMDB0000873 (4-Methylcatechol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra