4-Methylcatechol (BioCAD00000004454)

blood feces urine plant natural products microbial natural products

Metabolite Card

Formula: C7H8O2 (124.0524)
SMILES: CC1=CC=C(O)C(O)=C1

Synonyms [en]

4-methylcatechol; 4-methylbenzene-1,2-diol; 4-Methyl-1,2-benzenediol; 1,2-Dihydroxy-4-methylbenzene; Homopyrocatechol; 2-Hydroxy-4-methylphenol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

4-Methylcatechol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000004454). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 452-86-8
  • CAS Registry Number: 83719-41-9
  • PubChem: 9958
  • ChEBI: ChEBI:17254
  • HMDB: HMDB0000873
  • HMDB: HMDB00873
  • KEGG: C06730
  • BioCyc: 4-METHYLCATECHOL
  • NCBI MeSH: 4-methylcatechol
  • Wikipedia: 4-Methylcatechol
  • DrugBank: DB04120
  • RefMet: RM0022896
  • MoNA: BAF_UVA_POS000396
  • MoNA: BAF_UVA_POS000430
  • MoNA: BAF_UVA_POS000431
  • MoNA: BAF_UVA_POS000432
  • MoNA: CCMSLIB00000578362
  • MoNA: CCMSLIB00005463580
  • MoNA: CCMSLIB00005720854
  • MoNA: FiehnHILIC001000
  • MoNA: FiehnHILIC002536
  • MoNA: FiehnLib000145
  • MoNA: HMDB0000873_c_ms_99626
  • MoNA: HMDB0000873_ms_ms_1232
  • MoNA: HMDB0000873_ms_ms_1233
  • MoNA: HMDB0000873_ms_ms_1234
  • MoNA: MoNA033564
  • MoNA: MoNA033565
  • MoNA: MoNA033567
  • MoNA: MoNA034556
  • MoNA: MoNA034561
  • MoNA: MoNA034563
  • MoNA: MoNA035690
  • MoNA: MoNA035691
  • MoNA: MoNA035695
  • MoNA: MoNA037317
  • MoNA: MoNA037679
  • MoNA: MoNA038416
  • Metlin: METLIN_64945
  • Coconut NaturalProduct: CNP0017901.0
  • Coconut NaturalProduct: CNP0114802.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03568 1.14.13.7 4-cresol,NADPH:oxogen oxidoreductase (2-hydroxylating)
KEGG:R05292 1.3.1.67 cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate:NAD+ oxidoreductase (decarboxylating)
KEGG:R05293 1.3.1.67 cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate:NADP+ oxidoreductase (decarboxylating)
KEGG:R05294 1.14.12.14 toluene-4-sulfonate,NADH:oxygen oxidoreductase (3,4-hydroxylating, sulfite-forming)
KEGG:R05295 1.13.11.2 4-methylcatechol:oxygen 2,3-oxidoreductase(decyclizing)
KEGG:R05299 1.13.11.1 4-methylcatechol:oxygen 1,2-oxidoreductase(decyclizing)
KEGG:R06939 1.14.13.1 salicylate,NADH:oxygen oxidoreductase (1-hydroxylating,decarboxylating)
Rhea:RHEA:24225 1.3.1.67 (1R,6S)-1,6-dihydroxy-4-methylcyclohexa-2,4-diene-1-carboxylate + NADP+ => 4-methylcatechol + CO2 + NADPH
Rhea:RHEA:24226 1.3.1.67 4-methylcatechol + CO2 + NADPH => (1R,6S)-1,6-dihydroxy-4-methylcyclohexa-2,4-diene-1-carboxylate + NADP+
Rhea:RHEA:24227 1.3.1.67 (1R,6S)-1,6-dihydroxy-4-methylcyclohexa-2,4-diene-1-carboxylate + NADP+ <=> 4-methylcatechol + CO2 + NADPH
Rhea:RHEA:24229 1.3.1.67 (1R,6S)-1,6-dihydroxy-4-methylcyclohexa-2,4-diene-1-carboxylate + NAD+ => 4-methylcatechol + CO2 + NADH
Rhea:RHEA:24230 1.3.1.67 4-methylcatechol + CO2 + NADH => (1R,6S)-1,6-dihydroxy-4-methylcyclohexa-2,4-diene-1-carboxylate + NAD+
Rhea:RHEA:24231 1.3.1.67 (1R,6S)-1,6-dihydroxy-4-methylcyclohexa-2,4-diene-1-carboxylate + NAD+ <=> 4-methylcatechol + CO2 + NADH
Rhea:RHEA:57773 1.14.12.23 3-nitrotoluene + NADH + O2 => 4-methylcatechol + nitrite + NAD+
Rhea:RHEA:57774 1.14.12.23 4-methylcatechol + nitrite + NAD+ => 3-nitrotoluene + NADH + O2
Rhea:RHEA:57775 1.14.12.23 3-nitrotoluene + NADH + O2 <=> 4-methylcatechol + nitrite + NAD+
Rhea:RHEA:57797 1.14.12.23 4-nitrotoluene + NADH + O2 => 4-methylcatechol + nitrite + NAD+
Rhea:RHEA:57798 1.14.12.23 4-methylcatechol + nitrite + NAD+ => 4-nitrotoluene + NADH + O2
Rhea:RHEA:57799 1.14.12.23 4-nitrotoluene + NADH + O2 <=> 4-methylcatechol + nitrite + NAD+
Rhea:RHEA:62557 4.1.1.83 3,4-dihydroxyphenylacetate + H+ => 4-methylcatechol + CO2
View More
Organism Source

Taxonomy Source

  1. Acacia catechu [ncbi taxid: ]
  2. Bistorta manshuriensis [ncbi taxid: 1548133]
  3. Bistorta officinalis [ncbi taxid: 125587]
  4. Coffea arabica [ncbi taxid: 13443]
  5. Coffea canephora [ncbi taxid: 49390]
  6. Geosmithia langdonii [ncbi taxid: 240214]
  7. Homo sapiens [ncbi taxid: 9606]
  8. Picea abies [ncbi taxid: 3329]
  9. Rosa chinensis [ncbi taxid: 74649]
  10. Theobroma cacao [ncbi taxid: 3641]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-6954 superpathway of aromatic compound degradation via 2-hydroxypentadienoate
BioCyc:META_PWY-5183 superpathway of aerobic toluene degradation
BioCyc:META_PWY-5165 4-toluenesulfonate degradation II
BioCyc:META_TOLUENE-DEG-3-OH-PWY toluene degradation to 2-hydroxypentadienoate (via 4-methylcatechol)
BioCyc:META_PWY-5182 toluene degradation II (aerobic) (via 4-methylcatechol)
BioCyc:AURANTIMONAS_PWY-6184 methylsalicylate degradation
BioCyc:META_PWY-6184 methylsalicylate degradation
BioCyc:META_PWY-5427 naphthalene degradation (aerobic)
BioCyc:META_PWY-6185 4-methylcatechol degradation (ortho cleavage)
BioCyc:META_PWY-6956 naphthalene degradation to acetyl-CoA
BioCyc:AGRO_PWY-6184 methylsalicylate degradation
PathBank:SMP0002055 Thiazole Biosynthesis I
View All Pathways