Names | |
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Preferred IUPAC name 3-Methylbenzene-1,2-diol | |
Other names 2,3-Dihydroxytoluene 3-Methylpyrocatechol | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.006.975 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H8O2 | |
Molar mass | 124.139 g·mol−1 |
Appearance | white solid |
Density | g/cm3 |
Melting point | 68 °C (154 °F; 341 K) |
Boiling point | 241 °C (466 °F; 514 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
3-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol. Being structurally related to lignans, it is contributes to the aerosol generate by combustion of wood. [1]
The enzyme 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase uses 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate and NAD+ to produce 3-methylcatechol, NADH and CO2. [2]
The isofunctional enzymes of catechol 1,2-dioxygenase from species of Acinetobacter , Pseudomonas , Nocardia , Alcaligenes and Corynebacterium oxidize 3-methylcatechol according to both the intradiol and extradiol cleavage patterns. However, the enzyme preparations from Brevibacterium and Arthrobacter have only the intradiol cleavage activity. [3]
The 3-methylcatechol structural motif is rare in natural products. Known examples include calopin and a δ-lactone derivative, O-acetylcyclocalopin A|O-acetylcyclocalopin A, which have been isolated from the fungus Caloboletus calopus . [4]
Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables.
Aromatic-ring-hydroxylating dioxygenases (ARHD) incorporate two atoms of dioxygen (O2) into their substrates in the dihydroxylation reaction. The product is (substituted) cis-1,2-dihydroxycyclohexadiene, which is subsequently converted to (substituted) benzene glycol by a cis-diol dehydrogenase.
Homogentisic acid is a phenolic acid usually found in Arbutus unedo (strawberry-tree) honey. It is also present in the bacterial plant pathogen Xanthomonas campestris pv. phaseoli as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. It is oxidatively dimerised to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses.
Catechol dioxygenases are metalloprotein enzymes that carry out the oxidative cleavage of catechols. This class of enzymes incorporate dioxygen into the substrate. Catechol dioxygenases belong to the class of oxidoreductases and have several different substrate specificities, including catechol 1,2-dioxygenase, catechol 2,3-dioxygenase, and protocatechuate 3,4-dioxygenase. The active site of catechol dioxygenases most frequently contains iron, but manganese-containing forms are also known.
Catechol 1,2- dioxygenase is an enzyme that catalyzes the oxidative ring cleavage of catechol to form cis,cis-muconic acid:
Caloboletus calopus, commonly known as the bitter bolete, bitter beech bolete or scarlet-stemmed bolete, is a fungus of the bolete family, found in Asia, Northern Europe and North America. Appearing in coniferous and deciduous woodland in summer and autumn, the stout fruit bodies are attractively coloured, with a beige to olive cap up to 15 cm (6 in) across, yellow pores, and a reddish stipe up to 15 cm (6 in) long and 5 cm (2 in) wide. The pale yellow flesh stains blue when broken or bruised.
In enzymology, a 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase (EC 1.3.1.68) is an enzyme that catalyzes the chemical reaction
In enzymology, a cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate dehydrogenase (EC 1.3.1.67) is an enzyme that catalyzes the chemical reaction
In enzymology, a cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase (EC 1.3.1.56) is an enzyme that catalyzes the chemical reaction
In enzymology, a dibenzothiophene dihydrodiol dehydrogenase (EC 1.3.1.60) is an enzyme that catalyzes the chemical reaction
In enzymology, a 2-chlorobenzoate 1,2-dioxygenase (EC 1.14.12.13) is an enzyme that catalyzes the chemical reaction
In enzymology, a 2-nitrophenol 2-monooxygenase (EC 1.14.13.31) is an enzyme that catalyzes the chemical reaction
In enzymology, an anthranilate 1,2-dioxygenase (deaminating, decarboxylating) (EC 1.14.12.1) is an enzyme that catalyzes the chemical reaction
In enzymology, a benzoate 1,2-dioxygenase (EC 1.14.12.10) is an enzyme that catalyzes the chemical reaction
In enzymology, a biphenyl 2,3-dioxygenase (EC 1.14.12.18) is an enzyme that catalyzes the chemical reaction
In enzymology, a toluene dioxygenase (EC 1.14.12.11) is an enzyme that catalyzes the chemical reaction
Dioxygenases are oxidoreductase enzymes. Aerobic life, from simple single-celled bacteria species to complex eukaryotic organisms, has evolved to depend on the oxidizing power of dioxygen in various metabolic pathways. From energetic adenosine triphosphate (ATP) generation to xenobiotic degradation, the use of dioxygen as a biological oxidant is widespread and varied in the exact mechanism of its use. Enzymes employ many different schemes to use dioxygen, and this largely depends on the substrate and reaction at hand.
Microbial arene oxidation (MAO) refers to the process by which microbial enzymes convert aromatic compounds into more oxidized products. The initial intermediates are arene oxides. A number of oxidized products are possible, the most commonly employed for organic synthesis are cis-1,2-dihydroxy-cyclohexa-3,5-dienes ("dihydrodiols").
Rhamnolipids are a class of glycolipid produced by Pseudomonas aeruginosa, amongst other organisms, frequently cited as bacterial surfactants. They have a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail, such as 3-hydroxydecanoic acid.
4-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol.