Anthranilic Acid
(Synonyms: 邻氨基苯甲酸,NSC 144, NSC 40929) 目录号 : GC41593
An Analytical Reference Standard
Cas No.:118-92-3
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
Anthranilic Acid is a potential precursor in the synthesis of quinazolinones, including methaqualone.[1] For this reason, anthranilic acid, its esters, and its salts are categorized as List I chemicals with the Drug Enforcement Administration in the United States. Anthranilic acid is also a natural antimicrobial metabolite produced by a number of bacterial strains.[2] This product is intended for research and forensic applications.
邻氨基苯甲酸是合成喹唑啉酮（包括甲喹酮）的潜在前体。 [1]因此，邻氨基苯甲酸、其酯类及其盐类被美国缉毒署列为清单 I 化学品。邻氨基苯甲酸也是一种由许多细菌菌株产生的天然抗菌代谢物。 [2]本产品旨在用于研究和法医应用。
Reference:
[1]. Soliman, F.S., Shafik, R.M., and Elnenaey, E.A. Synthesis of methaqualone and its diphasic titration in pure and tablet forms. Journal of Pharmaceutical Sciences 67(3), 411-413 (1978).
[2]. Hund, H.K., de Beyer, A., and Lingens, F. Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp. Biological Chemistry of Hoppe-Seyler 371(10), 1005-1008 (1990).
| Cas No. | 118-92-3 | SDF | |
| 别名 | 邻氨基苯甲酸,NSC 144, NSC 40929 | ||
| 化学名 | 2-amino-benzoic acid | ||
| Canonical SMILES | OC(C1=C(N)C=CC=C1)=O | ||
| 分子式 | C7H7NO2 | 分子量 | 137.1 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 0.5 mg/ml | 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 | 7.2939 mL | 36.4697 mL | 72.9395 mL |
| 5 mM | 1.4588 mL | 7.2939 mL | 14.5879 mL |
| 10 mM | 0.7294 mL | 3.647 mL | 7.2939 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。
Medicinal chemistry of Anthranilic Acid derivatives: A mini review
Drug Dev Res 2021 Nov;82(7):945-958.PMID:34117784DOI:10.1002/ddr.21842.
Anthranilic Acid and its analogues present a privileged profile as pharmacophores for the rational development of pharmaceuticals deliberated for managing the pathophysiology and pathogenesis of various diseases. The substitution on Anthranilic Acid scaffold provides large compound libraries, which enable a comprehensive assessment of the structure activity relationship (SAR) analysis for the identification of hits and leads in a typical drug development paradigm. Besides, their widespread applications as anti-inflammatory fenamates, the amide and anilide derivatives of Anthranilic Acid analogues play a central role in the management of several metabolic disorders. In addition, these derivatives of Anthranilic Acid exhibit interesting antimicrobial, antiviral and insecticidal properties, whereas the derivatives based on anthranilic diamide scaffold present applications as P-glycoprotein inhibitors for managing the drug resistance in cancer cells. In addition, the Anthranilic Acid derivatives serve as the inducers of apoptosis, inhibitors of hedgehog signaling pathway, inhibitors of mitogen activated protein kinase pathway, and the inhibitors of aldo-keto reductase enzymes. The antiviral derivatives of Anthranilic Acid focus on the inhibition of hepatitis C virus NS5B polymerase to manifest considerable antiviral properties. The Anthranilic Acid derivatives reportedly present neuroprotective applications by downregulating the key pathways responsible for the manifestation of neuropathological features and neurodegeneration. Nevertheless, the transition metal complexes of Anthranilic Acid derivatives offer therapeutic applications in diabetes mellitus, and obesity by regulating the activity of α-glucosidase. The present review demonstrates a critical analysis of the therapeutic profile of the key derivatives of Anthranilic Acid and its analogues for the rational development of pharmaceuticals and therapeutic molecules.
An anthranilic acid-responsive transcriptional regulator controls the physiology and pathogenicity of Ralstonia solanacearum
PLoS Pathog 2022 May 26;18(5):e1010562.PMID:35617422DOI:10.1371/journal.ppat.1010562.
Quorum sensing (QS) is widely employed by bacterial cells to control gene expression in a cell density-dependent manner. A previous study revealed that Anthranilic Acid from Ralstonia solanacearum plays a vital role in regulating the physiology and pathogenicity of R. solanacearum. We reported here that Anthranilic Acid controls the important biological functions and virulence of R. solanacearum through the receptor protein RaaR, which contains helix-turn-helix (HTH) and LysR substrate binding (LysR_substrate) domains. RaaR regulates the same processes as Anthranilic Acid, and both are present in various bacterial species. In addition, anthranilic acid-deficient mutant phenotypes were rescued by in trans expression of RaaR. Intriguingly, we found that Anthranilic Acid binds to the LysR_substrate domain of RaaR with high affinity, induces allosteric conformational changes, and then enhances the binding of RaaR to the promoter DNA regions of target genes. These findings indicate that the components of the Anthranilic Acid signaling system are distinguished from those of the typical QS systems. Together, our work presents a unique and widely conserved signaling system that might be an important new type of cell-to-cell communication system in bacteria.
Nematicidal Anthranilic Acid derivatives from Laccaria species
Phytochemistry 2019 Apr;160:85-91.PMID:30802801DOI:10.1016/j.phytochem.2019.01.008.
Three undescribed natural products, the Anthranilic Acid derivatives laccanthrilic acids A, B, and C, as well as the known (3S)-1,2,3,4-tetrahydro-3-β-carboline-3-carboxylic acid were isolated from fruiting bodies of Laccaria laccata. The structures were established by 1D and 2D NMR spectroscopy, HR-(+)-ESIMS and chemical synthesis. The absolute configuration of laccanthrilic acids A and B was determined by GC-MS after hydrolytic cleavage and derivatisation of the resulting glutamic acid with methanol and Mosher's reagent and subsequent comparison with authentic synthetic samples of known absolute configuration. The absolute configuration of laccanthrilic acid C was determined by comparison of the CD spectra of laccanthrilic acids B and C with each other. Metabolic profiling of related species showed that the compounds are common in the genus Laccaria. Laccanthrilic acid B exhibited moderate nematicidal effects against Caenorhabditis elegans, which might explain to some degree the beneficial role of these fungi for the growth and survival of their host plants.
Anthranilic Acid Accumulation in Saccharomyces cerevisiae Induced by Expression of a Nonribosomal Peptide Synthetase Gene from Paecilomyces cinnamomeus BCC 9616
Chembiochem 2022 Dec 16;23(24):e202200573.PMID:36250803DOI:10.1002/cbic.202200573.
Heterologous expression of nrps33, a nonribosomal peptide synthetase gene, from Paecilomyces cinnamomeus BCC 9616 in Saccharomyces cerevisiae unexpectedly resulted in the accumulation of Anthranilic Acid, an intermediate in tryptophan biosynthesis. Based on transcriptomic and real-time quantitative polymerase chain reaction (RT-qPCR) results, expression of nrps33 affected the transcription of tryptophan biosynthesis genes especially TRP1 which is also the selectable auxotrophic marker for the expression vector used in this work. The product of nrps33 could inhibit the activity of Trp4 involved in the conversion of anthranilate to N-(5'-phosphoribosyl)anthranilate and therefore caused the accumulation of Anthranilic Acid. This accumulation could in turn result in down-regulation of downstream tryptophan biosynthesis genes. Anthranilic Acid is typically produced by chemical synthesis and has been used as a substrate for synthesising bioactive compounds including commercial drugs; our results could provide a new biological platform for production of this compound.
Anthranilic Acid from Ralstonia solanacearum plays dual roles in intraspecies signalling and inter-kingdom communication
ISME J 2020 Sep;14(9):2248-2260.PMID:32457502DOI:10.1038/s41396-020-0682-7.
Quorum sensing (QS) signals are widely utilized by bacteria to regulate biological functions in response to cell population density. Previous studies have demonstrated that Ralstonia solanacearum employs two different types of QS systems. We report here that Anthranilic Acid controls important biological functions and the production of QS signals in R. solanacearum. It was demonstrated that the biosynthesis of Anthranilic Acid is mainly performed by TrpEG. The accumulation of Anthranilic Acid and the transcription of trpEG occur in a cell density-dependent manner in R. solanacearum. Both the Anthranilic Acid and TrpEG homologues are conserved in various bacterial species. Moreover, we show that Sporisorium scitamineum sexual mating and hypha formation are strongly inhibited by the addition of exogenous Anthranilic Acid. Our results suggest that Anthranilic Acid is important for the physiology of bacteria in addition to its role in inter-kingdom communication.