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Methyl 2-(methylamino)benzoate

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Methyl 2-(methylamino)benzoate Basic information
Methyl 2-(methylamino)benzoate Chemical Properties
Safety Information
Methyl 2-(methylamino)benzoate Usage And Synthesis
  • DescriptionMethyl n-methylanthranilate has an orange and mandarin peel-like odor with a musty, grape-like flavor. It is somewhat more berry-like than grape. May be prepared by methylation of methyl anthranilate or esterification of N-methylanthranilic acid.
  • Chemical PropertiesMethyl-n-methylanthranilate has an orange and mandarin peel-like odor and a musty, grape-like flavor; somewhat more berry-like than grape.
  • Chemical PropertiesMethyl N-Methylanthranilate is the main component of petitgrain oils from mandarin leaves and is also found in mandarin oil. It is a pale yellow, fluorescent liquid with a delicate mandarin odor. The ester can be prepared by methylation ofmethyl anthranilate. It is used in soap and cosmetic perfumes as well as in aromas, particularly for mandarin flavors.
  • OccurrenceReported found in mandarin essential oil and mandarin leaves essential oil (50 to 76.5%); also reported in the oil from bulbs of Kaempferia ethelae L., in orange petitgrain, and in the oil from hyacinth flowers. Also reported found in starfruit, orange peel oil and grapefruit juice.
  • UsesIt is used as a flavorant in a wide range of foods (particularly flour and sugar confections).
  • Production MethodsMethyl N-methanthranilate is a component of mandarin and mandarin tree leaf essential oil. It is also found in oil from bulbs of Kaempferia ethelae L., hyacinth flowers, and orange petitgrain . It is synthesized by methylation of methyl anthranilate or esterification ofN-methylanthranilic acid.
  • PreparationBy methylation of methyl anthranilate or esterification of N-methylanthranillic acid.
  • Taste threshold valuesTaste characteristics at 10 ppm: fruity grape skin, anthranilate-like with a woody and floral nuance
  • Synthesis Reference(s)The Journal of Organic Chemistry, 49, p. 3373, 1984 DOI: 10.1021/jo00192a024
  • Toxicity evaluationThe acute oral LD50 value in rats was reported as 3.7 ml/kg (Levenstein, 1974). The acute oral LD50 in female rats was reported to be between 2.25 g/kg (no deaths) and 3.38 g/kg (100% deaths) (Gaunt, Sharratt, Grasso & Wright, 1970). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Levenstein, 1974). The LC 50 for larvae of Tribolium destructor was found to be 0-1151 mg/cm3 (Vasechko, Kuznetsov, Smelyanets & Guznenok, 1970).
  • Safety ProfilePoison by intravenous route. Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.
Methyl 2-(methylamino)benzoate Preparation Products And Raw materials
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