MiMeDB: Showing metabocard for 4-Methylcatechol (MMDBc0049908)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:59 UTC

Update Date

2024-10-09 21:35:00 UTC

Metabolite ID

MMDBc0049908

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

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

Molecular Formula

C₇H₈O₂

Average Mass

124.1372

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1930000000-6225053efa0739efca3d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1930000000-6225053efa0739efca3d	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-2d8d69f64905f6f9396e	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0udj-3940000000-d5331c4c752130a85084	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a6r-1900000000-9045a710867168d6cc51	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-0e20b47a091c0b3e39ab	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-0e20b47a091c0b3e39ab	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-0900000000-7db9fcc9e56ad8a39080	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9200000000-f6f538341319fcc5433b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-97cd131a887e2f870186	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-6981a2924f054e884c5c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-0aaf237b7039ed11a1d7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0553-9000000000-fe5754c269058c591feb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-c1c0f17738a12823f96d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-2900000000-e5f3b6d9329514c202a8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-d5abc716689493ede24f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-6bd82a87c9fe3a5ac3f7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03dj-9000000000-5833215eaa6163ad44f4	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-efa52ff0e22aa918c832	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-1813508ce877db8f3b51	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v00-9200000000-42f7207a63d63607822f	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-965e88496dc55d1d3a08	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-528bea85898c5bbee974	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9400000000-25d222489152bbee4894	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-2900000000-f83a6dc29f504d8a27ea	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9400000000-f09039303c5f740d5e99	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gdi-9000000000-5a1ebbe40df7d21e329f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2900000000-5af433d114ee67df4fda	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008233	3,4-Dihydroxybenzeneacetic acid	4-Methylcatechol	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	7	Human ; Human feces; Goat feces; Sheep feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Urine	Detected and Quantified	3.6	1.5	umol/mmol creatinine	Adult (>18 years old)	Male	Smoking	HMDB	6890513
Human Feces	Detected and Quantified	14.339		nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	1.8	1.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	6890513
Human Feces	Detected and Quantified	7.814	1.128	nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000873

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

References

Synthesis Reference

Not Available

General References

Scheline RR: Drug metabolism by intestinal microorganisms. J Pharm Sci. 1968 Dec;57(12):2021-37. doi: 10.1002/jps.2600571202. [PubMed:4974346 ]
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. doi: 10.1016/s0278-6915(82)80068-9. [PubMed:6890513 ]
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. doi: 10.1002/jps.2600700717. [PubMed:7264927 ]
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. doi: 10.1111/j.1365-2672.1995.tb03153.x. [PubMed:7592132 ]
Shen Y: In vitro cytotoxicity of BTEX metabolites in HeLa cells. Arch Environ Contam Toxicol. 1998 Apr;34(3):229-34. doi: 10.1007/s002449900310. [PubMed:9504968 ]
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. doi: 10.1046/j.1432-1327.1998.2570092.x. [PubMed:9799107 ]
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. doi: 10.1016/s0891-5849(98)00179-8. [PubMed:9890654 ]
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. doi: 10.1016/S0944-7113(99)80015-4. [PubMed:10589442 ]
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. doi: 10.1078/0944-7113-00080. [PubMed:11924762 ]
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. doi: 10.1128/AEM.70.3.1804-1810.2004. [PubMed:15006807 ]
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 ]

Showing metabocard for 4-Methylcatechol (MMDBc0049908)

MOL for #<Metabolite:0x00007fdaf238b308>

3D MOL for #<Metabolite:0x00007fdaf238b308>

3D SDF for #<Metabolite:0x00007fdaf238b308>

3D-SDF for #<Metabolite:0x00007fdaf238b308>

PDB for #<Metabolite:0x00007fdaf238b308>

3D PDB for #<Metabolite:0x00007fdaf238b308>

SMILES for #<Metabolite:0x00007fdaf238b308>

INCHI for #<Metabolite:0x00007fdaf238b308>

Structure for #<Metabolite:0x00007fdaf238b308>

3D Structure for #<Metabolite:0x00007fdaf238b308>