3,4-Dimethylbenzoic acid
(Synonyms: 3,4-二甲基苯甲酸) 目录号 : GC60494
3,4-Dimethylbenzoicacid是RhodococcusrhodochrousN75的苯甲酸二甲酯代谢产物。
Cas No.:619-04-5
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,4-Dimethylbenzoic acid acts as a product of dimethylbenzoate metabolism by Rhodococcus rhodochrous N75[1].
3,4-Dimethylbenzoic acid is oxidised by 4-methylbenzoate (p-toluate)-grown cells of Rhodococcus rhodochrous N75 via the ortho-pathway through the intermediates 3,4-dimethylcatechol[1].
[1]. StefanSchmidt, et al. Isolation and identification of two novel butenolides as products of dimethylbenzoate metabolism by Rhodococcus rhodochrous N75.
| Cas No. | 619-04-5 | SDF | |
| 别名 | 3,4-二甲基苯甲酸 | ||
| Canonical SMILES | O=C(O)C1=CC=C(C)C(C)=C1 | ||
| 分子式 | C9H10O2 | 分子量 | 150.18 |
| 溶解度 | 储存条件 | Store at -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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 6.6587 mL | 33.2934 mL | 66.5868 mL |
| 5 mM | 1.3317 mL | 6.6587 mL | 13.3174 mL |
| 10 mM | 0.6659 mL | 3.3293 mL | 6.6587 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
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。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Initial steps in the degradation of 3,4-Dimethylbenzoic acid by Pseudomonas putida strain DMB
FEMS Microbiol Lett 1996 Apr 1;137(2-3):129-34.PMID:8998974DOI:10.1111/j.1574-6968.1996.tb08094.x.
Pseudomonas putida strain DMB capable of growing on 3,4-Dimethylbenzoic acid as the only C and energy source was isolated by enrichment techniques. It does not utilize for growth or cooxidize the other dimethylbenzoate isomers tested. 3,4-Dimethylsalicylic acid, 3,4-dimethylphenol and 3,4-dimethylcatechol were isolated and identified by nuclear magnetic resonance and mass spectra in the reaction mixture of P. putida washed cells. The detection of the two first metabolites suggests that the initial step in the degradation of 3,4-Dimethylbenzoic acid is the formation of 3,4-dimethylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid which underwent an acid-catalyzed dehydration yielding 3,4-dimethylsalicylic acid and 3,4-dimethylphenol. Further degradation proceeds through 3,4-dimethylcatechol via the meta pathway.
Intermediates formed during natural attenuation of C9 aromatics under simulated marine conditions: Identification, transformation pathway, and toxicity to microalgae
Environ Res 2022 Apr 15;206:112558.PMID:34932976DOI:10.1016/j.envres.2021.112558.
C9 aromatics - benzene hydrocarbon containing nine carbon atoms among - leakage accident has caused serious damage to the marine ecology near Quangang District, Fujian Province, China. The ecological restoration of the accident sea area is basically realized through natural attenuation. To determine whether the natural attenuation of C9 aromatics in the marine environment will generate highly toxic intermediates, and thus cause more serious harm to marine ecology, the intermediates of C9 aromatics (n-propylbenzene, isopropylbenzene, 2-ethyltoluene, 3-ethyltoluene, 4-ethyltoluene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, and indene) in the process of natural attenuation were studied under the marine conditions simulated by a microcosm. The acute toxic effects of 12 intermediates with longer residual time on Phaeodactylum tricornutum were also ascertained. Twenty natural attenuation intermediates of C9 aromatics were identified. These products primarily include the derivatives of phenols, aromatic alcohols, aromatic aldehydes, aromatic ketones, and aromatic acids, as well as an aromatic lactone compound. No intermediates of 1,3,5-trimethylbenzene and indene during the attenuation process were determined. The indirect photooxidation initiated by hydroxyl radical might play an essential role in the formation of intermediates of C9 aromatic. Based on the 96-h EC50 values for P. tricornutum, the toxicity of the 12 intermediates, in descending order, was: 4-ethylphenol, 2-methylacetophenone, 2,3-dimethylbenzyl alcohol, 4-methylacetophenone, 3-methylacetophenone, 1-phenyl-1-propanol, 1-(2-methylphenyl) ethanol, 2-phenyl-2-propanol, 3,4-Dimethylbenzoic acid, 2,4-dimethylbenzoic acid, 2,5-dimethylbenzoic acid, then 4-tolylacetic acid. The 96-h EC50 values of the intermediates of C9 aromatics to P. tricornutum ranged from 8.4 to 199.1 mg/L, which were lower than that of their corresponding parent compound. The findings provided essential fundamental insights for the assessment of marine environmental risk of C9 aromatics leakage accidents, and subsequent emergency disposal countermeasures.
An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA)
Eur J Med Chem 2002 Oct;37(10):825-8.PMID:12446040DOI:10.1016/s0223-5234(02)01406-x.
5,6-Dimethylxanthenone-4-acetic acid (DMXAA) is a novel anticancer agent with a number of unique activities, and is in clinical trial. The current synthesis of DMXAA involves six steps, beginning with a heterogeneous reaction to form an isonitrosoacetanilide, and gives an overall yield of 11% from 2,3-dimethylaniline. We report an alternative synthesis of the key intermediate 3,4-dimethylanthranilic acid via nitration of 3,4-Dimethylbenzoic acid and separation of the key desired isomer by ready crystallisation. This, together with improvements in the rest of the synthesis, provide a shorter and higher-yielding route to DMXAA (22% overall from 3,4-Dimethylbenzoic acid).
Toxicokinetics and metabolism of pseudocumene (1,2,4-trimethylbenzene) after inhalation exposure in rats
Int J Occup Med Environ Health 2002;15(1):37-42.PMID:12038862doi
The objective of this study was to evaluate the toxicokinetics and metabolism of pseudocumene after inhalation exposure. Male Wistar rats were exposed to pseudocumene vapors at nominal concentrations of 25,100 or 250 ppm in the dynamic inhalation chambers for 6 h. Blood samples were collected during (between 1st and 6th h) and after exposure (betwen 6th min and 6th h). Blood concentrations of pseudocumene were estimated by gas chromatography using the headspace technique. During a six-hour exposure, the concentration of pseudocumene in blood increased rapidly within the first 2 h reaching then a plateau. The elimination of pseudocumene from blood followed an open two-compartment model. Urine samples were collected from the exposed animals, and metabolites were analyzed by gas chromatography with a flame ionization detector. Three metabolites were measured in the rat urine after hydrolysis: 3,4-Dimethylbenzoic acid (3,4-DMBA), 2,4-dimethylbenzoic acid (2,4-DMBA) and 2,5-dimethylbenzoic acid (2,5-DMBA). A significant linear correlation was found between the level of exposure and the concentration of dimethylbenzoic acids. The enzyme kinetics of pseudocumene biotransformation was calculated by Lineweaver-Burk equation. Metabolic constants, Km (mg/l) and Vmax (mg/h/kg), the parameters for pseudocumene biotransformation by rats were estimated (3,4-DMBA - Km = 28, Vmax = 96; 2,4-DMBA - Km = 7, Vmax = 25; 2,5-DMBA - Km = 7, Vmax = 23).
Species-specific enhancement of enterohemorrhagic E. coli pathogenesis mediated by microbiome metabolites
Microbiome 2019 Mar 20;7(1):43.PMID:30890187DOI:10.1186/s40168-019-0650-5.
Background: Species-specific differences in tolerance to infection are exemplified by the high susceptibility of humans to enterohemorrhagic Escherichia coli (EHEC) infection, whereas mice are relatively resistant to this pathogen. This intrinsic species-specific difference in EHEC infection limits the translation of murine research to human. Furthermore, studying the mechanisms underlying this differential susceptibility is a difficult problem due to complex in vivo interactions between the host, pathogen, and disparate commensal microbial communities. Results: We utilize organ-on-a-chip (Organ Chip) microfluidic culture technology to model damage of the human colonic epithelium induced by EHEC infection, and show that epithelial injury is greater when exposed to metabolites derived from the human gut microbiome compared to mouse. Using a multi-omics approach, we discovered four human microbiome metabolites-4-methyl benzoic acid, 3,4-Dimethylbenzoic acid, hexanoic acid, and heptanoic acid-that are sufficient to mediate this effect. The active human microbiome metabolites preferentially induce expression of flagellin, a bacterial protein associated with motility of EHEC and increased epithelial injury. Thus, the decreased tolerance to infection observed in humans versus other species may be due in part to the presence of compounds produced by the human intestinal microbiome that actively promote bacterial pathogenicity. Conclusion: Organ-on-chip technology allowed the identification of specific human microbiome metabolites modulating EHEC pathogenesis. These identified metabolites are sufficient to increase susceptibility to EHEC in our human Colon Chip model and they contribute to species-specific tolerance. This work suggests that higher concentrations of these metabolites could be the reason for higher susceptibility to EHEC infection in certain human populations, such as children. Furthermore, this research lays the foundation for therapeutic-modulation of microbe products in order to prevent and treat human bacterial infection.