Methyl anthranilate

Manufactured by Merck Group

Sourced in United States

Methyl anthranilate is a colorless to pale yellow liquid chemical compound. It is the methyl ester of anthranilic acid, with the molecular formula C8H9NO2. Methyl anthranilate is commonly used as a flavoring agent and an intermediate in the production of various chemical compounds.

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Anthranilate (5 citations)

8 protocols using methyl anthranilate

Spectral Analysis of Methyl Anthranilate

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NMR spectra were acquired by containing Me4Si as internal standard on Varian Unity-Inova 500 MHz and 125 MHz spectrometers (Varian Inc., Palo Alto, CA, USA) using solvent chloroform-d (Cambridge Isotope Laboratories (CIL), Inc., Tewksbury, MA, USA). ESI (electrospray ionization) low-resolution LC-MS data were obtained with an Agilent Technologies 6120 quadrupole mass system (Agilent Technologies, Santa Clara, CA, USA) and Waters Alliance Micromass ZQ LC-MS system (Waters Corp, Milford, MA, USA) using reversed-phase column (Phenomenex Luna C18 (2) 100 Å, 50 mm×4.6 mm, 5µm) (Phenomenex, Torrance, CA, USA) at a flow rate 1.0 mL/min at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University (Seoul, Korea). Methyl anthranilate with purity 98.0% was purchased from Sigma-Aldrich Co. LLC (St. Louis, MO, USA).
Methyl anthranilate : colorless to pale yellow liquid; ¹H NMR (500 MHz, CDCl3) : ^δ_H 7.85 (1H, dd, J=8.5, 1.7 Hz), 7.24 (1H, ddd, J=1.9 Hz, 7.4 Hz), 6.64 (1H, s), 6.63 (1H, m), 3.85 (1H, s, OCH₃); ¹³C NMR (125 MHz, CDCl₃) : ^δ_c 168.6, 150.5, 134.1, 131.2, 116.7, 116.2, 110.7, 51.5; LR-ESI-MS m/z : 151.17 [M+H]⁺.

Park H.J., Kim K., Lee E.Y., Hillman P.F., Nam S.J, & Lim K.M. (2024). Methylanthranilate, a Food Fragrance Attenuates Skin Pigmentation through Downregulation of Melanogenic Enzymes by cAMP Suppression. Biomolecules & Therapeutics, 32(2), 231-239.

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Thrips Attractants from Tea and Plants

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Twenty types of compounds, derived from tea plants and plant-derived semiochemicals attracted to other thrips, were used in our trials [4 (link),24 (link),25 (link),26 (link)]. In particular, 4-acetylpyridine, p-anisaldehyde, decanal, eugenol, farnesene (mixture of isomers, α-farnesene, and (E)-β-farnesene), geraniol, (Z)-3-hexenol, (Z)-3-hexenyl butyrate, limonene, methyl anthranilate, methyl benzoate, 3-methyl butanal, methyl isonicotinate, methyl salicylate, β-myrcene, nonanal, (E)-β-ocimene, (−)-α-pinene, (+)-α-pinene, and γ-terpinene were all purchased from Sigma-Aldrich (St. Louis, MO, United States) (Table S1). Hexane (HPLC grade, CNW Technologies GmbH (Düsseldorf, Germany)) was chosen as solvent, and the abovementioned synthetic volatiles were diluted to a specific concentration.

Xiu C., Zhang F., Pan H., Bian L., Luo Z., Li Z., Fu N., Cai X, & Chen Z. (2022). Evaluation of Selected Plant Volatiles as Attractants for the Stick Tea Thrip Dendrothrips minowai in the Laboratory and Tea Plantation. Insects, 13(6), 509.

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Synthesis of Methyl Anthranilate Silver Nanoparticles

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Methyl anthranilate was procured from Sigma Aldrich (Mumbai, India), and silver nitrate in the form of solid crystals was purchased from Thomas Baker (Mumbai, India). Methanol was of HPLC grade and purchased from S.D. Fine Chemicals Ltd. (Mumbai, India). Triethanolamine and polyethylene glycol (PEG) were obtained from S.D. Fine Chemicals Ltd. (Mumbai, India). Carbopol-934 was purchased from B.S. Goodrich, Pleveland. Other agents used in experimentation were of analytical grade.

Ghazwani M., Hani U., Alqarni M.H, & Alam A. (2023). Development and Characterization of Methyl-Anthranilate-Loaded Silver Nanoparticles: A Phytocosmetic Sunscreen Gel for UV Protection. Pharmaceutics, 15(5), 1434.

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Synthesis of N-octanoylanthranilic Acid

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The PQS cleavage product, N-octanoylanthranilic acid, was synthesized according to the method described by Wells et al. (1952 (link)) with some modifications. Briefly, octanoyl chloride (Sigma Aldrich, Taufkirchen, Germany) was added dropwise to a solution of methyl anthranilate (Sigma Aldrich, Taufkirchen, Germany) dissolved in ethyl acetate at 0°C while stirring. Following heating to 50°C for 5 min the solution was stirred over night at room temperature resulting in a clear solution. Subsequently, this solution was successively washed with water, 1 M sodium hydroxide, 1 M hydrochloric acid and finally with brine. After drying with Na₂SO₄ the organic solvent was removed by evaporation leading to a crude oil of methyl N-octanoylanthranilate which was used without further purification. Hydrolysis of the acylated anthranilate was carried out with 0.5 M sodium hydroxide solved in ethanol. The reaction mixture was refluxed for 3 h. After cooling, the solution was acidified with 4 M hydrochloric acid and extracted two times with n-hexane. Evaporation yielded crude N-octanoylanthranilic acid which was recrystallized in n-hexane. ESI-TOF/MS for C₁₅H₂₂NO₃⁺ ([M + H]⁺): calculated m/z = 264.159; found m/z = 264.114.
CORM-2, a carbon monoxide releasing molecule, and PQS were purchased from Sigma Aldrich (Taufkirchen, Germany).

Tettmann B., Niewerth C., Kirschhöfer F., Neidig A., Dötsch A., Brenner-Weiss G., Fetzner S, & Overhage J. (2016). Enzyme-Mediated Quenching of the Pseudomonas Quinolone Signal (PQS) Promotes Biofilm Formation of Pseudomonas aeruginosa by Increasing Iron Availability. Frontiers in Microbiology, 7, 1978.

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Analytical Standards for Aroma Compounds

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Dichloromethane, ethyl acetate, absolute ethanol (99%), and anhydrous sodium sulfate were purchased from VWR International (Leuven, Belgium). Standards of ethyl benzoate, methyl anthranilate, phenylacetaldehyde, 2-methylbutanal, 3-methylbutanal, heptan-2-one, heptan-2-ol, 2-methylbutyl acetate, trans-2-nonenal, methional, isobutyl acetate, benzaldehyde, myrcene, linalool, ethyl heptanoate, ethyl octanoate, 2-phenylethyl acetate, ethyl acetate, ethyl butanoate, isoamyl propionate, acetophenone, and 2-acetylthiophene were purchased from Sigma-Aldrich (Bornem, Belgium). Standard of nonan-2-one was purchased from Janssen Chimica (Geel, Belgium). Standards of dimethyltrisulfide and 1-octen-3-ol were purchased from Acros Organics (Geel, Belgium). Standard of 3-methylbutan-1-ol was purchased from Merck Millipore (Burlington, NJ, USA). Standard of acetoin was purchased from Supelco (Bellefonte, PA, USA).

Collin S., Fisette T., Pinto A., Souza J, & Rogez H. (2023). Discriminating Aroma Compounds in Five Cocoa Bean Genotypes from Two Brazilian States: White Kerosene-like Catongo, Red Whisky-like FL89 (Bahia), Forasteros IMC67, PA121 and P7 (Pará). Molecules, 28(4), 1548.

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Synthesis and Purification of DNP-Amino Acids

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Dinitrophenylated (DNP) amino acids—DNP-alanine, DNP-norvaline, DNP-norleucine, and DNP-α-amino-n-octanoic acid, were purchased from Sigma–Aldrich. The sodium salts of the DNP-amino acids were prepared by titration as described in [10 (link),11 (link),13 (link),14 (link),15 (link),16 (link),17 (link),18 (link),19 (link)]. Adenine, adenosine, adenosine monophosphate Na salt, adenosine diphosphate Na salt, adenosine triphosphate Na salt, 4-amino phenol, benzyl alcohol, caffeine, coumarin, methyl anthranilate, p-nitrophenyl-α-D-glucopyranoside, sorbitol, sucrose, trehalose, phenol, 2-phenylethanol, trimethylamine N-oxide (TMAO), and vanillin were purchased from Sigma-Aldrich and used without further purification as reported in [10 (link),11 (link),13 (link),14 (link),15 (link),16 (link),17 (link),18 (link),19 (link)].

da Silva N.R., Ferreira L.A., Madeira P.P., Teixeira J.A., Uversky V.N, & Zaslavsky B.Y. (2020). Linear Relationships between Partition Coefficients of Different Organic Compounds and Proteins in Aqueous Two-Phase Systems of Various Polymer and Ionic Compositions. Polymers, 12(7), 1452.

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Solvatochromic Probes and Osmolytes

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Polyethylene glycol-8000 (Lot 091M01372 V) with an average molecular weight (M w ) of 8000 and polyethylene glycol-10000 (Lot 043K2522) with an average molecular weight (M w ) of 10000 were purchased from Sigma-Aldrich (St. Louis, MO, USA). The solvatochromic probes 4-nitro phenol (reagent grade, >98%) was purchased from Aldrich (Milwaukee, WI, USA) and 4-nitroanisole (>97%, GC) was received from Acros Organics. Reichardt's carboxylated betaine dye, 2,6-diphenyl-4-[2,6diphenyl-4-(4-carboxyphenyl)-1-pyridino]phenolate, sodium salt was kindly provided by Professor C. Reichardt (Philipps University, Marburg, Germany).
Sorbitol, trimethylamine N-oxide (TMAO), and trehalose were purchased from Sigma-Aldrich, and sucrose was received from USB (Cleveland, OH, USA). 4-Amino phenol, benzyl alcohol, caffeine; coumarin, methylanthranilate, 4-nitrophenyl-␣-D-glucopyranoside, phenol, 2-phenylethanol, vanillin, and o-phthaldialdehyde (OPA) reagent (complete) were purchased from Sigma-Aldrich. All compounds were of 98-99% purity and used as received without further purification. All salts and other chemicals used were of analytical-reagent grade.

da Silva N.R., Ferreira L.A., Madeira P.P., Teixeira J.A., Uversky V.N, & Zaslavsky B.Y. (2015). Analysis of partitioning of organic compounds and proteins in aqueous polyethylene glycol-sodium sulfate aqueous two-phase systems in terms of solute-solvent interactions. Journal of chromatography. A, 1415.

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Solvatochromic Probes and Osmolytes

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Polyethylene glycol-8000 (Lot 091M01372V) with an average molecular weight (M w ) of 8,000 and polyethylene glycol-10000 (Lot 043K2522) with an average molecular weight (M w ) of 10,000 were purchased from Sigma-Aldrich (St. Louis, MO, USA). The solvatochromic probes 4-nitro phenol (reagent grade, >98%) was purchased from Aldrich (Milwaukee, WI, USA) and 4-nitroanisole (>97%, GC) was received from Acros Organics. Reichardt's carboxylated betaine dye, 2,6-diphenyl-4-[2,6-diphenyl-4-(4-carboxyphenyl)-1-pyridino]phenolate, sodium salt was kindly provided by Professor C. Reichardt (Philipps University, Marburg, Germany).
Sorbitol and trimethylamine N-oxide (TMAO) were purchased from Sigma-Aldrich, and sucrose was received from USB (Cleveland, OH, USA). Benzyl alcohol, caffeine; coumarin, methyl anthranilate, 4-nitrophenyl-␣-d-glucopyranoside, phenol, 2-phenylethanol, vanillin, and o-phthaldialdehyde (OPA) reagent (complete) were purchased from Sigma-Aldrich. All compounds were of 98-99% purity and used as received without further purification. All salts and other chemicals used were of analytical-reagent grade.

da Silva N.R., Ferreira L.A., Madeira P.P., Teixeira J.A., Uversky V.N, & Zaslavsky B.Y. (2015). Effect of sodium chloride on solute-solvent interactions in aqueous polyethylene glycol-sodium sulfate two-phase systems. Journal of chromatography. A, 1425.

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