3-Methoxycatechol
(Synonyms: 3-甲氧基儿茶酚) 目录号 : GC49874
A lignan-derived phenol
Cas No.:934-00-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-Methoxycatechol is a lignan-derived phenol.1 It is an agonist of G protein-coupled receptor 35 (GPR35) with an EC50 value of 147 µM in a dynamic mass redistribution (DMR) assay using HT-29 cells.2 Dietary administration of 3-methoxycatechol (2%) alone, or in a model of multiorgan carcinogenesis induced by nitrosamines, promotes esophageal carcinogenesis in rats.3 3-Methoxycatechol has been used as a precursor in the enzymatic synthesis of the phenols pyrogallol and purpurogallin and in the electro-organic synthesis of coumestan derivatives.1,4
1.Zhang, S., Xiaofeng, W., and Xiao, Y.Conversion of lignin-derived 3-methoxycatechol to the natural product purpurogallin using bacterial P450 GcoAB and laccase CueOAppl. Microbiol. Biotechnol.106(2)593-603(2022) 2.Deng, H., and Fang, Y.The three tatecholics benserazide, catechol and pyrogallol are GPR35 agonistsPharmaceuticals (Basel)6(4)500-509(2013) 3.Hirose, M., Tnaka, H., Takahashi, S., et al.Effects of sodium nitrite and catechol, 3-methoxycatechol, or butylated hydroxyanisole in combination in a rat multiorgan carcinogenesis modelCancer Res.53(1)32-37(1993) 4.Golabi, S.M., and Nematollahi, D.Electrochemical study of catechol and some 3-substituted catechols in the prescence of 4-hydroxy coumarin: Application to the electro-organic synthesis of new coumestan derivativesJ. Electroanal. Chem.420(1-2)127-134(1997)
| Cas No. | 934-00-9 | SDF | Download SDF |
| 别名 | 3-甲氧基儿茶酚 | ||
| Canonical SMILES | OC1=CC=CC(OC)=C1O | ||
| 分子式 | C7H8O3 | 分子量 | 140.1 |
| 溶解度 | DMF: 3 mg/ml,DMSO: 2 mg/ml,Ethanol: 2 mg/ml,PBS (pH 7.2): 2 mg/ml | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.1378 mL | 35.6888 mL | 71.3776 mL |
| 5 mM | 1.4276 mL | 7.1378 mL | 14.2755 mL |
| 10 mM | 0.7138 mL | 3.5689 mL | 7.1378 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
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Conversion of lignin-derived 3-Methoxycatechol to the natural product purpurogallin using bacterial P450 GcoAB and laccase CueO
Appl Microbiol Biotechnol 2022 Jan;106(2):593-603.PMID:34971410DOI:10.1007/s00253-021-11738-5.
Purpurogallin is a natural benzotropolone extracted from Quercus spp, which has antioxidant, anticancer, and anti-inflammatory properties. Purpurogallin is typically synthesized from pyrogallol using enzymatic or metal catalysts, neither economically feasible nor environmentally friendly. 3-Methoxycatechol (3-MC) is a lignin-derived renewable chemical with the potential to be a substrate for the biosynthesis of purpurogallin. In this study, we designed a pathway to produce purpurogallin from 3-MC. We first characterized four bacterial laccases and identified the laccase CueO from Escherichia coli, which converts pyrogallol to purpurogallin. Then, we used CueO and the P450 GcoAB reported to convert 3-MC to pyrogallol, to construct a method for producing purpurogallin directly from 3-MC. A total of 0.21 ± 0.05 mM purpurogallin was produced from 5 mM 3-MC by whole-cell conversion. This study provides a new method to enable efficient and sustainable synthesis of purpurogallin and offers new insights into lignin valorization. KEY POINTS: • Screening four bacterial laccases for converting pyrogallol to purpurogallin. • Laccase CueO from Escherichia coli presenting the activity for purpurogallin yield. • A novel pathway for converting lignin-derived 3-Methoxycatechol to purpurogallin.
Effects of sodium nitrite and catechol or 3-Methoxycatechol in combination on rat stomach epithelium
Jpn J Cancer Res 1990 Sep;81(9):857-61.PMID:2121686DOI:10.1111/j.1349-7006.1990.tb02657.x.
The effects of sodium nitrite (NaNO2) and catechol or 3-Methoxycatechol in combination were examined in male F344 rats. Animals were treated with 0.3% NaNO2 in the drinking water and 0.8% catechol or 2% 3-Methoxycatechol in powdered diet for 24 weeks. While catechol or 3-Methoxycatechol alone induced low incidences of mild or moderate hyperplasia, simultaneous administration of NaNO2 markedly enhanced the degree of hyperplasia and papilloma formation. In contrast, induction of submucosal hyperplasia and adenomas in the glandular epithelium was reduced. Thus, the results indicate that NaNO2 can modulate the metabolism of antioxidants, so that, possibly via production of new active moieties, targeting of forestomach epithelium is enhanced.
Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-Methoxycatechol, methoxyhydroquinone, and methylhydroquinone
J Bacteriol 2004 Jul;186(14):4705-13.PMID:15231803DOI:10.1128/JB.186.14.4705-4713.2004.
Wild-type toluene 4-monooxygenase (T4MO) of Pseudomonas mendocina KR1 oxidizes toluene to p-cresol (96%) and oxidizes benzene sequentially to phenol, to catechol, and to 1,2,3-trihydroxybenzene. In this study T4MO was found to oxidize o-cresol to 3-methylcatechol (91%) and methylhydroquinone (9%), to oxidize m-cresol and p-cresol to 4-methylcatechol (100%), and to oxidize o-methoxyphenol to 4-methoxyresorcinol (87%), 3-Methoxycatechol (11%), and methoxyhydroquinone (2%). Apparent Vmax values of 6.6 +/- 0.9 to 10.7 +/- 0.1 nmol/min/ mg of protein were obtained for o-, m-, and p-cresol oxidation by wild-type T4MO, which are comparable to the toluene oxidation rate (15.1 +/- 0.8 nmol/min/mg of protein). After these new reactions were discovered, saturation mutagenesis was performed near the diiron catalytic center at positions I100, G103, and A107 of the alpha subunit of the hydroxylase (TmoA) based on directed evolution of the related toluene o-monooxygenase of Burkholderia cepacia G4 (K. A. Canada, S. Iwashita, H. Shim, and T. K. Wood, J. Bacteriol. 184:344-349, 2002) and a previously reported T4MO G103L regiospecific mutant (K. H. Mitchell, J. M. Studts, and B. G. Fox, Biochemistry 41:3176-3188, 2002). By using o-cresol and o-methoxyphenol as model substrates, regiospecific mutants of T4MO were created; for example, TmoA variant G103A/A107S produced 3-methylcatechol (98%) from o-cresol twofold faster and produced 3-Methoxycatechol (82%) from 1 mM o-methoxyphenol seven times faster than the wild-type T4MO (1.5 +/- 0.2 versus 0.21 +/- 0.01 nmol/min/mg of protein). Variant I100L produced 3-Methoxycatechol from o-methoxyphenol four times faster than wild-type T4MO, and G103S/A107T produced methylhydroquinone (92%) from o-cresol fourfold faster than wild-type T4MO and there was 10 times more in terms of the percentage of the product. Variant G103S produced 40-fold more methoxyhydroquinone from o-methoxyphenol than the wild-type enzyme produced (80 versus 2%) and produced methylhydroquinone (80%) from o-cresol. Hence, the regiospecific oxidation of o-methoxyphenol and o-cresol was changed for significant synthesis of 3-Methoxycatechol, methoxyhydroquinone, 3-methylcatechol, and methylhydroquinone. The enzyme variants also demonstrated altered monohydroxylation regiospecificity for toluene; for example, G103S/A107G formed 82% o-cresol, so saturation mutagenesis converted T4MO into an ortho-hydroxylating enzyme. Furthermore, G103S/A107T formed 100% p-cresol from toluene; hence, a better para-hydroxylating enzyme than wild-type T4MO was formed. Structure homology modeling suggested that hydrogen bonding interactions of the hydroxyl groups of altered residues S103, S107, and T107 influence the regiospecificity of the oxygenase reaction.
Effects of sodium nitrite and catechol, 3-Methoxycatechol, or butylated hydroxyanisole in combination in a rat multiorgan carcinogenesis model
Cancer Res 1993 Jan 1;53(1):32-7.PMID:8416747doi
Effects of simultaneous treatment with NaNO2 and butylated hydroxyanisole, catechol, or 3-Methoxycatechol were examined in a rat multiorgan carcinogenesis model. Groups of 15 animals were given a single i.p. injection of 100 mg/kg of body weight diethylnitrosamine, 4 i.p. injections of 20 mg/kg of body weight N-methylnitrosourea, 4 s.c. injections of 40 mg/kg of body weight dimethylhydrazine, p.o. treatment with 0.05% N-butyl-N-(4-hydroxybutyl)nitrosamine in the drinking water for the first 2 weeks and p.o. treatment with 0.1% 2,2'-dihydroxy-di-n-propylnitrosamine in the drinking water for the next 2 weeks of the initial 4-week initiation period. Starting 3 days after the completion of these carcinogen treatments, animals were given diets containing 2% butylated hydroxyanisole, 0.8% catechol, 2% 3-Methoxycatechol, or basal diet either alone or in combination with 0.3% sodium nitrite until week 28, when complete autopsy was performed. Histological examination showed that NaNO2 strongly enhanced development of forestomach lesions but inhibited that of glandular stomach lesions in rats simultaneously given catechol or 3-Methoxycatechol with or without prior carcinogen exposure. 3-Methoxycatechol promoted esophageal carcinogenesis either with or without NaNO2, but promoting effects of catechol were evident only in the presence of NaNO2. In addition, treatment with NaNO2 after carcinogen exposure enhanced forestomach carcinogenesis. These results indicate that NaNO2 can modify phenolic antioxidant-induced cell proliferation and/or carcinogenesis, particularly in the upper digestive tract.
Oxidation of Catechols at the Air-Water Interface by Nitrate Radicals
Environ Sci Technol 2022 Nov 15;56(22):15437-15448.PMID:36318667DOI:10.1021/acs.est.2c05640.
Abundant substituted catechols are emitted to, and created in, the atmosphere during wildfires and anthropogenic combustion and agro-industrial processes. While ozone (O3) and hydroxyl radicals (HO•) efficiently react in a 1 μs contact time with catechols at the air-water interface, the nighttime reactivity dominated by nitrate radicals (NO3) remains unexplored. Herein, online electrospray ionization mass spectrometry (OESI-MS) is used to explore the reaction of NO3(g) with a series of representative catechols (catechol, pyrogallol, 3-methylcatechol, 4-methylcatechol, and 3-Methoxycatechol) on the surface of aqueous microdroplets. The work detects the ultrafast generation of nitrocatechol (aromatic) compounds, which are major constituents of atmospheric brown carbon. Two mechanisms are proposed to produce nitrocatechols, one (equivalent to H atom abstraction) following fast electron transfer from the catechols (QH2) to NO3, forming NO3- and QH2•+ that quickly deprotonates into a semiquinone radical (QH•). The second mechanism proceeds via cyclohexadienyl radical intermediates from NO3 attack to the ring. Experiments in the pH range from 4 to 8 showed that the production of nitrocatechols was favored under the most acidic conditions. Mechanistically, the results explain the interfacial production of chromophoric nitrocatechols that modify the absorption properties of tropospheric particles, making them more susceptible to photooxidation, and alter the Earth's radiative forcing.