18189-02-1

Usage

Uses

Used in the Fragrance Industry:
Isopropyl anthranilate is used as a fragrance ingredient for its fruity, sweet, and floral odor, adding a pleasant scent to personal care products such as perfumes and lotions.
Used in the Food Industry:
Isopropyl anthranilate is used as a flavoring agent for its grape-like aroma, often added to beverages and confectionery to enhance their taste and aroma profile.

InChI:InChI=1/C8H15NO2/c1-3-10-8(11-4-2)6-5-7-9/h8H,3-6H2,1-2H3

Upstream product

• 947-80-8 isopropyl 2-nitrobenzoate 
• 118-92-3 anthranilic acid 
• 67-63-0 isopropyl alcohol 
• 118-48-9 isatoic anhydride 
• 612-25-9 2-Nitrobenzyl alcohol 
• 134-20-3 2-carbomethoxyaniline 
• 64001-48-5 2-(sulfinylamino)benzoyl chloride 

Downstream Products

• 100116-61-8 N-chloroacetyl-anthranilic acid isopropyl ester 
• 1366542-29-1 isopropyl 2-(4-methoxycyclohexylamino)benzoate 
• 1366542-32-6 isopropyl 2-(4-methoxycyclohexylamino)benzoate 
• 180335-18-6 C₁₆H₁₇N₃O₂ 
• 101689-26-3 2-(4-Hydroxy-3,6-dioxo-5-undecyl-cyclohexa-1,4-dienylamino)-benzoic acid isopropyl ester 

Relevant academic research and scientific papers

Synthesis of 3-phenylbenzo[c]isoxazoles by thermocyclization of 2-azidobenzophenones

3-Phenylbenzo[c]isoxazoles were synthesized by non-catalytic thermolysis of 2-azidobenzophenones in dry xylene with quantitative yields. The trace content of water in solvents reduces the yields of the reaction products. 2-Azidobenzoic acid esters are sta

Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists

Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here we analyzed structure-activity relationships of a battery of 36 non-steroidal structural variants of methyl anthranilate including 23 synthesized compounds. We identified structural requirements that lead to more potent AR antagonists. Specific compounds inhibit the transactivation of wild-type AR as well as AR mutants that render treatment resistance to hydroxyflutamide, bicalutamide and the second-generation AR antagonist enzalutamide. This suggests a distinct mode of inhibiting the AR compared to the clinically used compounds. Competition assays suggest binding of these compounds to the AR ligand binding domain and inhibit PCa cell proliferation. Moreover, active compounds induce cellular senescence despite inhibition of AR-mediated transactivation indicating a transactivation-independent AR-pathway. In line with this, fluorescence resonance after photobleaching (FRAP) - assays reveal higher mobility of the AR in the cell nuclei. Mechanistically, fluorescence resonance energy transfer (FRET) - assays indicate that the amino-carboxy (N/C)-interaction of the AR is not affected, which is in contrast to known AR-antagonists. This suggests a mechanistically novel mode of AR-antagonism. Together, these findings indicate the identification of a novel chemical platform as a new lead structure that extends the diversity of known AR antagonists and possesses a distinct mode of antagonizing AR-function.

Transition-metal-catalyst-free synthesis of anthranilic acid derivatives by transfer hydrogenative coupling of 2-nitroaryl methanols with alcohols/amines

By using a transfer hydrogenative coupling strategy, we herein describe a new method for the efficient synthesis of anthranilic acid derivatives, a significantly important class of compounds with extensive applications in organic synthesis and the discovery of bioactive molecules, from 2-nitroaryl methanols and readily available alcohols/amines. The synthesis proceeds with the merits of no need for a transition metal catalyst, operational simplicity, broad substrate scope, good functional tolerance, and high step efficiency, which offers a useful alternative to access anthranilic acid derivatives.

Preparation method of anthranilate and amide compounds

The invention discloses a preparation method of anthranilate and amide compounds. The method comprises the following steps: adding an aromatic compound containing adjacent hydroxymethyl and nitro substituent groups, an alcohol or an amine and a solvent into a reactor, adding an alkali as a promoter, introducing an inert gas, carrying out a stirring reaction at 100-110 DEG C for 16-20 h, and carrying out separation and purification to obtain the anthranilate or amide compounds. The preparation method has the advantages of simple synthesis steps, safety in operation, non-toxicity and low price of raw materials, high yield of the final product, and facilitation of industrial production.

Potassium phosphate / benzyltriethylammonium chloride as efficient catalytic system for transesterification

Potassium phosphate (K3PO4) in the presence of benzyltriethylammonium chloride have been found to catalyses the transesterifications of a wide variety of aliphatic and aromatic esters with primary and secondary alcohols affording the corresponding esters in good-to-excellent yields.

On the reaction of anthranilic acid with thionyl chloride: Iminoketene intermediate formation

2-(Sulfinylamino) benzoyl chloride is formed on treating anthranilic acid with thionyl chloride. The formation of iminoketene intermediate from 2-(sulfinylamino) benzoyl chloride is established and the reactions carried out using the intermediate are described.

2-Arylaminopyrimidine derivatives as PLK inhibitors

Anilino-pyrimidine and 1,2,4-triazine compounds (1) are new. Anilino-pyrimidine and 1,2,4-triazine compounds of formula (1), their tautomers, racemates, enantiomers and/or diastereomers and acid-addition salts are new. X : NR 1a>, O or S; Y : CH or N; Z : hydrogen, halo, (halo)1-3C alkyl, 2-3C alkenyl, 2-3C alkynyl, formyl, 1-3C (halo)alkylcarbonyl, 2-3C alkenyl-, 2-3C alkynyl-carbonyl or pseudohalo; A : (hetero)aryl group (i) or (ii); R a> - R f>e.g. hydrogen, halo or nitro; R 1> and R 1a>hydrogen or methyl; R 2>e.g. Cl, Br, I, OR 6>; R 3>e.g. -CONR 1>-L-Q 3-Q 4-R 9>, -NR 1>-CO-L-Q 3-Q 4-R 9>; R 4>e.g. OR 6>, COR 6>, CONR 6>R 7>, NR 6>R 7>, NR 6>COR 7>, NR 6>SO 2R 7>, N=CR 6>R 7>, SR 6>, SOR 6>, SO 2R 6>, SO 2NR 6>R 7> or pseudohalogen, or any of 1-8C alkyl, 2-10C alkenyl or alkynyl, 3-8C cycloalkyl, (hetero)aryl or heterocyclyl; R 5>hydrogen, halo, trifluoromethyl, 1-3C alkyl or OR 6>; R 6>, R 7>e.g. hydrogen or any of 1-5C alkyl, 2-5C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; L : e.g. bond or residue of 1-16C alkyl, 2-16C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; Q 3 and Q 4bond or a mono- or bi-cyclic heterocyclyl, optionally substituted by one or more of Me, Et, halo, amino, hydroxy or pseudohalo; R 9>as L but not a bond; and T : N, O or S. Full definitions are given in the DEFINITIONS (Full Definitions) field. [Image] [Image] ACTIVITY : Cytostatic; Antiinflammatory; Immunosuppressive; Virucide; Anti-HIV; Dermatological; Nootropic; Neuroprotective; Nephrotropic; Vulnerary; Antibacterial; Fungicide; Antiparasitic; Antipsoriatic; Osteopathic; Cardiovascular-Gen; Vasotropic; Gastrointestinal-Gen. MECHANISM OF ACTION : Kinase inhibitor; Polo-like kinase (PLK) inhibitor. In a trial, (1) was found to have EC 50 against recombinant human PLK1 of below 5, generally 1 mu M. No results for specific compounds were given.

Na2CO3/SOCl2: A mild and convenient reagent for the preparation of isopropyl carboxylates

Na2CO3/SOCl2 has been used for esterification of aliphatic and aromatic acids with isopropanol. This esterification method is compatible with a wide assortment of functional groups.

Steric effects in acid-catalyzed decomposition and base-catalyzed cyclization of 1-(2-alkoxycarbonyl-phenyl)-3-phenyltriazenes

Eight derivatives of 1-(2-alkoxycarbonylphenyl)-3-phenyltriazene (R = methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, and allyl) have been synthesized and their UV-VIS, IR, 1H and 13C NMR spectra measured. The NMR spectra have been interpreted in detail. The kinetics of acid-catalyzed decomposition and base-catalyzed cyclization of the title compounds have been measured in 52.1% w/w methanol at 25.0 °C. The unit reaction order has been verified and the cyclization product has been identified. The pH-profiles obtained have been used to calculate the catalytic rate constants kA (acid-catalyzed decomposition) and kB (base-catalyzed cyclization) of all the derivatives; the constants have been interpreted with regard to inductive and steric effects. The catalytic rate constant kA has been found to be independent of the substituents. The catalytic rate constant kB depends statistically significantly upon both inductive and steric effects, the sensitivity to the former being more significant. The experimental results and their interpretation confirm the base-catalyzed cyclization mechanism with formation of tetrahedral intermediate as the rate-limiting step.