452-86-8 Usage
Description
4-Methylcatechol, also known as 4-methyl-1,2-benzenediol, is an organic compound belonging to the class of catechols. It is characterized by the presence of a methyl group attached to the 4-position of the benzene ring and two hydroxyl groups at the 1,2-positions. This structure endows 4-methylcatechol with unique chemical and biological properties, making it a versatile compound for various applications.
Uses
Used in Chemical Synthesis:
4-Methylcatechol is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional groups make it a valuable building block for the development of new molecules with potential applications in different industries.
Used in Antimicrobial Applications:
4-Methylcatechol is used as an antimicrobial agent, exhibiting broad-spectrum activity against various microorganisms, including bacteria, fungi, and viruses. Its antimicrobial properties can be attributed to its ability to disrupt cell membranes, interfere with essential cellular processes, and generate reactive oxygen species, leading to the inhibition or killing of pathogens.
Used in Antioxidant Applications:
4-Methylcatechol is used as an antioxidant, protecting cells and tissues from oxidative damage caused by reactive oxygen species. Its phenolic hydroxyl groups can scavenge free radicals, chelate metal ions, and prevent lipid peroxidation, thereby reducing oxidative stress and promoting overall health.
Used as an Inhibitor:
4-Methylcatechol acts as an effective inhibitor in various chemical and biological processes. It can be used to modulate enzyme activity, control the rate of chemical reactions, or interfere with the growth and proliferation of undesirable organisms, making it a useful tool in research and industrial applications.
Used in the Production of 4-Bromo-5-Methyl-Pyrocatechol:
4-Methylcatechol is used as a starting material in the synthesis of 4-bromo-5-methyl-pyrocatechol, a compound with potential applications in the pharmaceutical and chemical industries. The bromination and methylation of 4-methylcatechol can lead to the formation of this valuable derivative, expanding the range of applications for this versatile compound.
Used in Neuroprotection and Neuroregeneration:
4-Methylcatechol has been shown to increase brain-derived neurotrophic factor (BDNF) content and mRNA expression in cultured brain cells and in rat brain in vivo. This suggests that it may have neuroprotective and neuroregenerative properties, potentially benefiting conditions associated with neurodegeneration, such as Alzheimer's disease, Parkinson's disease, and stroke.
Purification Methods
Crystallise the catechol from *C6H6. The purity is checked by TLC. Crystallise it from high-boiling pet ether and distil it in a vacuum. [Beilstein 6 IV 5878.]
Check Digit Verification of cas no
The CAS Registry Mumber 452-86-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 2 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 452-86:
(5*4)+(4*5)+(3*2)+(2*8)+(1*6)=68
68 % 10 = 8
So 452-86-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
452-86-8Relevant articles and documents
Epoxidation of styrenes with the peroxidase from the cultured cells of Nicotiana tabacum
Hirata, Toshifumi,Izumi, Shunsuke,Ogura, Masayuki,Yawata, Takayuki
, p. 15993 - 16003 (1998)
An enzyme concerned with the epoxidation of styrenes was isolated from cultured cells of Nicotiana tabacum. The enzyme had peroxidase activity as well as epoxidation activity, and its amino acid sequence showed 89% homology in their 9 amino acid overlap with horseradish peroxidase. In the enzymatic reaction, hydrogen peroxide and p-cresol were necessary and molecular oxygen was the source of the oxygen atom of the epoxide. The enzymatic reaction using a spin trap reagent and monitoring of the reaction with ESR indicated that the epoxidation reaction of styrenes proceeded by a radical mechanism with peroxidase.
Selective C-C Bond Cleavage of Methylene-Linked Lignin Models and Kraft Lignin
Shuai, Li,Sitison, Jake,Sadula, Sunitha,Ding, Junhuan,Thies, Mark C.,Saha, Basudeb
, p. 6507 - 6512 (2018)
Biorefinery and paper pulping lignins, referred hereto as technical lignins, contain condensed C-C interunit linkages. These robust C-C linkages with higher bond dissociation energies are difficult to disrupt under hydrogenolysis conditions, which are gen
Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives
Grimm, Christopher,Kroutil, Wolfgang,Pompei, Simona,Schiller, Christine,Schober, Lukas
supporting information, p. 16906 - 16910 (2021/07/02)
Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.
Selective ether bond breaking method of aryl alkyl ether
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Paragraph 0109-0113, (2020/09/16)
The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.
