p-Toluic acid
(Synonyms: 对甲基苯甲酸; 4-Methylbenzoic acid) 目录号 : GC39427
p-Toluic acid (4-Methylbenzoic acid) 是一种被取代的苯甲酸，是合成对氨基甲基苯甲酸 (PAMBA)，对甲苯腈等的中间体。
Cas No.:99-94-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
p-Toluic acid (4-Methylbenzoic acid) is a substituted benzoic acid and can be used as an intermediate for the synthesis of para-aminomethylbenzoic acid (PAMBA), p-tolunitrile, etc.
| Cas No. | 99-94-5 | SDF | |
| 别名 | 对甲基苯甲酸; 4-Methylbenzoic acid | ||
| Canonical SMILES | O=C(O)C(C=C1)=CC=C1C | ||
| 分子式 | C8H8O2 | 分子量 | 136.15 |
| 溶解度 | DMSO : 100 mg/mL (734.48 mM; Need ultrasonic) | 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。 |
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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 | 7.3448 mL | 36.7242 mL | 73.4484 mL |
| 5 mM | 1.469 mL | 7.3448 mL | 14.6897 mL |
| 10 mM | 0.7345 mL | 3.6724 mL | 7.3448 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。
Hepatotoxicological potential of p-Toluic acid in humanised-liver mice investigated using simplified physiologically based pharmacokinetic models
Xenobiotica 2021 Jun;51(6):636-642.PMID:33781181DOI:10.1080/00498254.2021.1908643.
p-Toluic acid, a metabolite of organic solvent xylene, has a high reported no-observed-effect level (NOEL, 1000 mg/kg) in rats, possibly because of direct glycine conjugation to methylhippuric acid. In this study, plasma levels of p-Toluic acid and its glycine conjugate in mice and humanised-liver mice were evaluated after oral administrations.Although rapid conversion of p-Toluic acid to its glycine conjugate was evident from mouse plasma concentrations, the biotransformation of p-Toluic acid was slower in humanised-liver mice. The input parameters for physiologically based pharmacokinetic (PBPK) models were determined using fitting procedures to create PBPK-generated plasma concentration curves.The PBPK-modelled hepatic concentrations of p-Toluic acid in humanised-liver mice were higher than those observed in plasma. PBPK-modelled hepatic and plasma concentrations of p-Toluic acid also indicated slow elimination in humans.These results suggest that rapid conjugations of p-Toluic acid reportedly observed in rats could result in overestimation of NOELs for conjugatable chemicals when extrapolated to humanised-liver mice or humans.
Efficient Syntheses of Biobased Terephthalic Acid, p-Toluic acid, and p-Methylacetophenone via One-Pot Catalytic Aerobic Oxidation of Monoterpene Derived Bio- p-cymene
ACS Sustain Chem Eng 2021 Jun 28;9(25):8642-8652.PMID:35024250DOI:10.1021/acssuschemeng.1c02605.
An efficient elevated-pressure catalytic oxidative process (2.5 mol % Co(NO3)2, 2.5 mol % MnBr2, air (30 bar), 125 °C, acetic acid, 6 h) has been developed to oxidize p-cymene into crystalline white terephthalic acid (TA) in ∼70% yield. Use of this mixed Co2+/Mn2+ catalytic system is key to obtaining high 70% yields of TA at relatively low reaction temperatures (125 °C) in short reaction times (6 h), which is likely to be due to the synergistic action of bromine and nitrate radicals in the oxidative process. Recycling studies have demonstrated that the mixed metal catalysts present in recovered mother liquors could be recycled three times in successive p-cymene oxidation reactions with no loss in catalytic activity or TA yield. Partial oxidation of p-cymene to give p-methylacetophenone (p-MA) in 55-60% yield can be achieved using a mixed CoBr2/Mn(OAc)2 catalytic system under 1 atm air for 24 h, while use of Co(NO3)2/MnBr2 under 1 atm O2 for 24 h gave p-Toluic acid in 55-60% yield. Therefore, access to these simple catalytic aerobic conditions enables multiple biorenewable bulk terpene feedstocks (e.g., crude sulfate turpentine, turpentine, cineole, and limonene) to be converted into synthetically useful bio-p-MA, bio-p-toluic acid, and bio-TA (and hence bio-polyethylene terephthalate) as part of a terpene based biorefinery.
Rotational Spectroscopy of p-Toluic acid and Its 1:1 Complex with Water
J Phys Chem A 2017 Nov 16;121(45):8625-8631.PMID:29049883DOI:10.1021/acs.jpca.7b08984.
The structure and internal dynamics of p-Toluic acid and its 1:1 complex with water were investigated in the gas phase using chirped-pulse and cavity-based Fourier transform microwave spectroscopy. One conformer and one isomer were identified for the monomer and monohydrate, respectively. In the monohydrate, water acts as both a hydrogen bond donor and acceptor, participating in a six-membered intermolecular ring with the carboxyl group. Both a- and b-type transitions were observed for the monomer; only a-type transitions were observed for the monohydrate. Rotational transitions of both species show splittings originating from methyl internal rotation, for which the potentials include 3- and 6-fold symmetry terms of similar amplitude. For the monomer, a few b-type transitions are missing, and their intensities were found to be transferred to c-type transitions with common energy levels, which are otherwise forbidden. No splittings attributable to a water internal tunneling motion were observed for the monohydrate. Furthermore, the absence of c-type transitions in the spectrum of the monohydrate, despite the large μc dipole moment component of the equilibrium geometry obtained by ab initio calculations, is consistent with a barrierless wagging motion of the free hydrogen of water, leading to an average μc dipole moment component of zero. These results provide insights regarding the interactions between atmospheric p-Toluic acid and water in prenucleation complexes and at the air-water interface of aqueous aerosols, where p-Toluic acid may act as a surfactant.
Effects of the headspace gas composition on anaerobic biotransformation of o-, m-, and p-Toluic acid in sediment slurries
J Environ Sci Health A Tox Hazard Subst Environ Eng 2003 Jun;38(6):1099-113.PMID:12774912DOI:10.1081/ese-120019867.
Composition of the headspace gas affected the biotransformation pattern of toluic acid isomers in anoxic sediment slurries. Under an N2 atmosphere, o- and m-, and p-Toluic acid (20-25 mg L(-1)) were biotransformed in 100 days, 77 days, and 148 days, respectively, with a lag period of 50 days, 49 days, and 50 days, respectively. Under a CO2 atmosphere, the same toluic acid isomers were biotransformed by the sediment microorganisms in 16-25 days without a lag period. CO2 thus increased the biotransformation rates. The presence of H2, on the other hand, decreased the biotransformation rates: in most cases, adding H2 gas (5% and 20% to the N2 and CO2 atmospheres, respectively) not only increased the lag period but also decreased the maximum biotransformation rates. These effects were especially noticeable for the N2 atmosphere. Under N2, the maximum biotransformation rates of the toluic acid isomers were in the order o-toluic acid > m-toluic acid > p-Toluic acid. However, under CO2, the maximum biotransformation rates were reversed, i.e., p-Toluic acid > m-toluic acid > o-toluic acid. The presence of the methanogen inhibitor bromoethanesulfonic acid (BESA) slowed the biotransformation rates of p-Toluic acid, and this together with the population dynamics of the acetogenic bacteria in the sediment slurries, suggested that acetogenic bacteria were involved in the degradation pathway. However, their exact role remains unclear.
Biotransformation of p-Toluic acid in anoxic estuarine sediments under a CO2 or N2/H2 atmosphere
Chemosphere 2001 Nov;45(6-7):835-42.PMID:11695603DOI:10.1016/s0045-6535(01)00098-4.
The composition of the headspace gas affected the growth dynamics of microbial populations and the biotransformation pattern of p-Toluic acid in anoxic estuarine sediments. Under CO2 atmosphere, p-Toluic acid was transformed by the sediment microorganisms without a lag period, while under N2/H2 atmosphere, p-Toluic acid was transformed after a lag period of 55 days. Under the N2/H2 atmosphere, the methanogen population, following a rapid increase of almost two orders of magnitude, remained at a high level until just before the onset of biotransformation. We hypothesize that during the lag period, the hydrogenotrophic methanogens were removing the H2, a step which is essential before the reaction can be exergonic. Acetogenic bacteria did not initiate decarboxylation as the first step of biotransformation under either atmosphere. Neither the methanogens nor the acetogenic bacteria appeared to be directly involved in the biotransformation of p-Toluic acid under either atmosphere. Under the CO2 atmosphere, biotransformation of p-Toluic acid involved sulfate-reducing bacteria, while under N2/H2, both sulfate-reducing bacteria and other eubacteria were involved.