Home>>Analytical Standards>>N-Acetylanthranilic Acid

N-Acetylanthranilic Acid

(Synonyms: 2-乙酰氨基苯甲酸) 目录号 : GC40943

An Analytical Reference Standard

N-Acetylanthranilic Acid Chemical Structure

Cas No.:89-52-1

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产品描述

N-Acetylanthranilic acid is a substrate that can be used in the synthesis of methaqualone in the absence of a catalyst. It is also an antimicrobial metabolite produced by a number of bacterial strains. It can be produced by the enzymatic degradation of quinaldine or by hydrolysis of benzoylchymotrypsin. N-Acetylanthranilic acid displays antimicrobial activity against some plant pathogens.

Chemical Properties

Cas No. 89-52-1 SDF
别名 2-乙酰氨基苯甲酸
Canonical SMILES OC(C1=C(NC(C)=O)C=CC=C1)=O
分子式 C9H9NO3 分子量 179.2
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
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1 mM 5.5804 mL 27.9018 mL 55.8036 mL
5 mM 1.1161 mL 5.5804 mL 11.1607 mL
10 mM 0.558 mL 2.7902 mL 5.5804 mL
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Research Update

N-Acetylborrelidin B: a new bioactive metabolite from Streptomyces mutabilis sp. MII

Z Naturforsch C J Biosci 2018 Jan 26;73(1-2):49-57.PMID:29055178DOI:10.1515/znc-2017-0140.

In the course of our screening program for new bioactive compounds, a naturally new 18-membered macrolide antibiotic, N-acetylborrelidin B (1) along with borrelidin (2) were obtained from the marine Streptomyces mutabilis sp. MII. The strain was isolated from a sediment sample collected in the Red Sea at the Hurghada Coast and characterized taxonomically. Additional nine diverse bioactive compounds were reported: 6-prenyl-indole-3-acetonitrile (3), sitosteryl-3β-d-glucoside, campesterol, ferulic acid, linoleic acid methyl ester, linoleic acid, N-Acetylanthranilic Acid, indole 3-acetic acid methyl ester, indole 3-carboxylic acid, and adenosine. Structure 1 was confirmed by in-depth NMR studies and by mass spectra, and comparison with related literature data. The antimicrobial activity of the strain extract and compounds 1 and 2 were studied using a panel of pathogenic microorganisms. The in vitro cytotoxicity of compounds 1 and 2 as well as the crude extract were tested against the human cervix carcinoma cell line (KB-3-1).

Metabolism of o-[methyl-14C]toluidine in the F344 rat

Xenobiotica 1980 Jul-Aug;10(7-8):457-68.PMID:7445517DOI:10.3109/00498258009033781.

1. Following a single dose (400 mg/kg s.c.) of o-[methyl-14C]toluidine to male F344 rats, 56% of the 14C was recovered in the 24 h urine, 2.3% in the faeces and 1% as exhaled 14CO2. After 48 h, 83.9% of the 14C appeared in the urine, 3.3% in the faeces and 1.4% was exhaled. 2. Ether-extractable urinary metabolites were separated by h.p.l.c. and identified as: o-toluidine (5.1% dose); azoxytoluene (0.2%); o-nitrosotoluene (less than or equal to 0.1%); N-acetyl-o-toluidine (0.2%); N-acetyl-o-aminobenzyl alcohol (0.3%); 4-amino-m-cresol (0.6%); N-acetyl-4-amino-m-cresol (0.3%); anthranilic acid (0.3%) and N-Acetylanthranilic Acid (0.3%). 3. Acid-conjugated urinary metabolites (51% of dose), separated by paper electrophoresis and by Sephadex LH-20 chromatography, were identified as sulphates of 4-amino-m-cresol (27.8% dose), N-acetyl-4-amino-m-cresol (8.5%), and 2-amino-m-cresol (2.1%), and glucuronides of 4-amino-m-cresol (2.6%), N-acetyl-4-amino-m-cresol (2.8%) and N-acetyl-o-aminobenzyl alcohol. Evidence for a double acid conjugate of 4-amino-m-cresol was also found. 4. These results show that N-acetylation and hydroxylation at the 4 position of o-toluidine are major metabolic pathways in the rat. Minor pathways include hydroxylation at the 6 position, oxidation of the methyl group and oxidation of the amino group. Sulphate conjugates predominate over glucuronides by a ratio of 6:1.

Synthesis of methaqualone and its diphasic titration in pure and tablet forms

J Pharm Sci 1978 Mar;67(3):411-3.PMID:641736DOI:10.1002/jps.2600670339.

A one-step synthesis of methaqualone from N-Acetylanthranilic Acid and o-toluidine in the absence of a catalyst is described. A rapid diphasic titration procedure for its microestimation in pure and tablet forms, using dioctyl sodium sulfosuccinate and dimethyl yellow screened with oracet blue B, is proposed. The data were compared with those obtained from nonaqueous titration methods.

Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp

Biol Chem Hoppe Seyler 1990 Oct;371(10):1005-8.PMID:2076195DOI:10.1515/bchm3.1990.371.2.1005.

Quinaldine catabolism was investigated with the bacterial strain Arthrobacter sp., which is able to grow aerobically in a mineral salt medium with quinaldine as sole source of carbon, nitrogen and energy. The following degradation products of quinaldine were isolated from the culture fluid and identified: 1H-4-oxoquinaldine, N-acetylisatic acid, N-Acetylanthranilic Acid, anthranilic acid, 3-hydroxy-N-acetylanthranilic acid and catechol. 3-Hydroxy-N-acetylanthranilic acid was not further metabolized by this organism. A degradation pathway is proposed.

Synthesis and Resolution of Quinazolinone Atropisomeric Phosphine Ligands(,)

J Org Chem 1998 Apr 17;63(8):2597-2600.PMID:11672124DOI:10.1021/jo972105z.

The syntheses of 2-methyl-3-[2'-(diphenylphosphino)phenyl]-4(3H)-quinazolinone (MPQ, 1a) and methyl-substituted analogues were achieved in good yield by coupling N-Acetylanthranilic Acid with the corresponding phosphinoanilines. Resolution of ligand 1bwas achieved using (-)-di-&mgr;-chlorobis[(S)-dimethyl-(1-phenylethyl)aminato-C(2),N]dipalladium(II) (5). The resulting crystalline complex (S,R)-6 served to unambiguously assign the absolute configuration of antipode (R)-(-)-1b. A practical resolution of this series of ligands 1a-c was accomplished using the (benzenesulfonyl)hydrazone derivative of camphorsulfonic acid (7) as a resolving agent.