4-Methylcatechol
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.
| 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 |
| Rhea:RHEA:62558 | 4.1.1.83 | 4-methylcatechol + CO2 => 3,4-dihydroxyphenylacetate + H+ |
| Rhea:RHEA:62559 | 4.1.1.83 | 3,4-dihydroxyphenylacetate + H+ <=> 4-methylcatechol + CO2 |
| BioCyc:RXN-10080 | 4-METHYLCATECHOL + OXYGEN-MOLECULE --> CPD-10656 + 2 PROTON | |
| BioCyc:1.3.1.67-RXN | 1.3.1.67 | NAD-P-OR-NOP + CIS-12-DIHYDROXY-ETCETERA-CARBOXYLATE<=>CARBON-DIOXIDE + NADH-P-OR-NOP + 4-METHYLCATECHOL |
| BioCyc:M-CRESOL-METHYLCATECHOL-RXN | 1.14.13.236 | m-cresol-methylcatechol |
| BioCyc:RXN-11219 | 1.13.11.2 | 4-METHYLCATECHOL + OXYGEN-MOLECULE --> CPD-8781 + PROTON |
| BioCyc:RXN-10078 | 1.14.13.1 | 4-methylsalicylate hydroxylase |
| BioCyc:RXN-20409 | 4.1.1.83 | CPD-782 + PROTON --> 4-METHYLCATECHOL + CARBON-DIOXIDE |
| BioCyc:RXN-10079 | 1.14.13.1 | 5-methylsalicylate hydroxylase |
| BioCyc:TSDOSALCAL-RXN | 1.14.12.- | 4-TOLUENESULFONATE + NADH + OXYGEN-MOLECULE --> SO3 + 4-METHYLCATECHOL + NAD |