Phenoxyacetic acid
(Synonyms: 苯氧乙酸) 目录号 : GC39787
Phenoxyacetic acid 是一种内源性代谢产物。
Cas No.:122-59-8
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
Phenoxyacetic acid is an endogenous metabolite.
| Cas No. | 122-59-8 | SDF | |
| 别名 | 苯氧乙酸 | ||
| Canonical SMILES | O=C(O)COC1=CC=CC=C1 | ||
| 分子式 | C8H8O3 | 分子量 | 152.15 |
| 溶解度 | DMSO : 50 mg/mL (328.62 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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。
Phenoxyacetic acid herbicides and chlorophenols and the etiology of lymphoma and soft-tissue neoplasms
Public Health Rev 1989;17(1):1-37.PMID:2485916doi
The Phenoxyacetic acid herbicides and the chlorophenols are compounds of economic importance. The herbicide 2,4-D is widely used in agriculture, industry, and the home. Recently, concern has arisen over their safety as a result of studies linking these compounds with soft-tissue sarcomas and non-Hodgkin's lymphomas. We reviewed the available literature in order to advise a provincial government regulatory body and investigated methodologic issues by examining the pattern of reported cases in Alberta. We conclude that, taking into account the serious limitations on methodology in the available data, the evidence for a causal association is strongest for non-Hodgkin's lymphomas and probably reflects either a weak effect or, possibly, a confounding exposure associated with the use of 2,4-D. Given the worst-case assumptions, however, the potency of 2,4-D as a carcinogen is probably weak. Its intrinsic toxicity is less than that of alternative herbicides and the hazard posed by its use is probably much less than either the use of chemical alternatives or manual cleaning of vegetation, which carry a high risk of occupational injuries.
Comparative inter-species pharmacokinetics of Phenoxyacetic acid herbicides and related organic acids. evidence that the dog is not a relevant species for evaluation of human health risk
Toxicology 2004 Jul 15;200(1):1-19.PMID:15158559DOI:10.1016/j.tox.2004.03.005.
Phenoxyacetic acids including 2,4-dichlorophenoxyacetic acid (2,4-D) and 4-chloro-2-methylphenoxyacetic acid (MCPA) are widely utilized organic acid herbicides that have undergone extensive toxicity and pharmacokinetic analyses. The dog is particularly susceptible to the toxicity of phenoxyacetic acids and related organic acids relative to other species. Active renal clearance mechanisms for organic acids are ubiquitous in mammalian species, and thus a likely mechanism responsible for the increased sensitivity of the dog to these agents is linked to a lower capacity to secrete organic acids from the kidney. Using published data describing the pharmacokinetics of phenoxyacetic and structurally related organic acids in a variety of species including humans, inter-species comparative pharmacokinetics were evaluated using allometic parameter scaling. For both 2,4-D and MCPA, the dog plasma half-life (t(1/2)) and renal clearance (Clr; mL/h) rates did not scale as a function of body weight across species; whereas for all other species evaluated, including humans, these pharmacokinetic parameters reasonably scaled. This exceptional response in the dog is clearly illustrated by comparing the plasma t(1/2) at comparable doses of 2,4-D and MCPA, across several species. At a dosage of 5mg/kg, in dogs, the plasma t(1/2) for 2,4-D and MCPA were approximately 92-106 and 63 h, respectively, which is substantially longer than in the rat (approximately 1 and 6 h, respectively) or in humans (12 and 11 h, respectively). This longer t(1/2), and slower elimination in the dog, results in substantially higher body burdens of these organic acids, at comparable doses, relative to other species. Although these results indicate the important role of renal transport clearance mechanisms as determinants of the clearance and potential toxicity outcomes of Phenoxyacetic acid herbicides across several species, other contributing mechanisms such as reabsorption from the renal tubules is highly likely. These findings suggest that for new structurally similar organic acids, a limited comparative species (rat versus dog) pharmacokinetic analysis early in the toxicology evaluation process may provide important insight into the relevance of the dog. In summary, the substantial difference between the pharmacokinetics of phenoxyacetic acids and related organic acids in dogs relative to other species, including humans, questions the relevance of using dog toxicity data for the extrapolation of human health risk.
Solid-phase extraction of Phenoxyacetic acid herbicides in complex samples with a zirconium(IV)-based metal-organic framework
J Sep Sci 2019 Jun;42(12):2148-2154.PMID:30997954DOI:10.1002/jssc.201900243.
A zirconium(IV)-based metal-organic framework material (MOF-808) has been synthesized in a simple way and used for the extraction of phenoxyacetic acids in complex samples. The material has good thermal and chemical stability, large specific surface area (905.36 m²/g), and high pore size (22.18 Å). Besides, it contains a large amount of Zr-O groups, easy-to-form Zr-O-H bond with carboxyl groups of phenoxyacetic acids, and possesses biphenyl skeleton structure, easy to interact with compounds through π-π and hydrophobic interactions. These characteristics make the material very suitable for the extraction of certain compounds with a high extraction efficiency and excellent selectivity. The extraction conditions were optimized, and then an analytical method was successfully established and applied for analysis of actual samples. The solid-phase extraction method based on prepared material had a wide linear range of 0.2-250 μg/L and a low detection limit of 0.1-0.5 μg/L for four Phenoxyacetic acid compounds including 2,4-dichlorophenoxyacetic acid, 2-(2,4-dichlorophenoxy) propionic acid, 4-chlorophenoxyacetic acid, and dicamba. The relative standard deviations of intra- and interday precision were 1.8-3.8 and 4.3-6.9%, and the recoveries after spiking were between 77.1 and 109.3%. The results showed that the material is a desired substituent for the extraction of compounds with benzene ring structure containing carboxyl groups.
Chiral Phenoxyacetic acid analogues inhibit colon cancer cell proliferation acting as PPARγ partial agonists
Sci Rep 2019 Apr 1;9(1):5434.PMID:30931956DOI:10.1038/s41598-019-41765-2.
Peroxisome Proliferator-Activated Receptor γ (PPARγ) is an important sensor at the crossroad of diabetes, obesity, immunity and cancer as it regulates adipogenesis, metabolism, inflammation and proliferation. PPARγ exerts its pleiotropic functions upon binding of natural or synthetic ligands. The molecular mechanisms through which PPARγ controls cancer initiation/progression depend on the different mode of binding of distinctive ligands. Here, we analyzed a series of chiral Phenoxyacetic acid analogues for their ability to inhibit colorectal cancer (CRC) cells growth by binding PPARγ as partial agonists as assessed in transactivation assays of a PPARG-reporter gene. We further investigated compounds (R,S)-3, (S)-3 and (R,S)-7 because they combine the best antiproliferative activity and a limited transactivation potential and found that they induce cell cycle arrest mainly via upregulation of p21waf1/cip1. Interestingly, they also counteract the β-catenin/TCF pathway by repressing c-Myc and cyclin D1, supporting their antiproliferative effect. Docking experiments provided insight into the binding mode of the most active compound (S)-3, suggesting that its partial agonism could be related to a better stabilization of H3 rather than H11 and H12. In conclusion, we identified a series of PPARγ partial agonists affecting distinct pathways all leading to strong antiproliferative effects. These findings may pave the way for novel therapeutic strategies in CRC.
Design, synthesis, and biological evaluation of novel dual FFA1 and PPARδ agonists possessing Phenoxyacetic acid scaffold
Bioorg Med Chem 2022 Feb 15;56:116615.PMID:35051813DOI:10.1016/j.bmc.2022.116615.
The free fatty acid receptor 1 (FFA1/GPR40) and peroxisome proliferator-activated receptor δ (PPARδ) have been widely considered as promising targets for type 2 diabetes mellitus (T2DM) due to their respective roles in promoting insulin secretion and improving insulin sensitivity. Hence, the dual FFA1/PPARδ agonists may exert synergistic effects by simultaneously activating FFA1 and PPARδ. The present study performed systematic exploration around previously reported FFA1 agonist 2-(2-fluoro-4-((2'-methyl-4'-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3-yl)methoxy)phenoxy)acetic acid (lead compound), leading to the identification of a novel dual FFA1/PPARδ agonist 2-(2-fluoro-4-((3-(6-methoxynaphthalen-2-yl)benzyl)oxy)phenoxy)acetic acid (the optimal compound), which displayed high selectivity over PPARα and PPARγ. In addition, the docking study provided us with detailed binding modes of the optimal compound in FFA1 and PPARδ. Furthermore, the optimal compound exhibited greater glucose-lowering effects than lead compound, which might attribute to its synergistic effects by simultaneously modulating insulin secretion and resistance. Moreover, the optimal compound has an acceptable safety profile in the acute toxicity study at a high dose of 500 mg/kg Therefore, our results provided a novel dual FFA1/PPARδ agonist with excellent glucose-lowering effects in vivo.