Methyl 2-(methylamino)benzoate

Description

Methyl 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 properties

Methyl 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.

Chemical properties

Methyl-n-methylanthranilate has an orange and mandarin peel-like odor and a musty, grape-like flavor; somewhat more berry-like than grape.

Occurrence

Reported 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.

The Uses of Methyl 2-(methylamino)benzoate

Methyl 2-(Methylamino)benzoate is one of many volatile components from mango cultivars.

The Uses of Methyl 2-(methylamino)benzoate

It is used as a flavorant in a wide range of foods (particularly flour and sugar confections).

Production Methods

Methyl 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.

Definition

ChEBI: Methyl N-methylanthranilate is a methyl ester resulting from the formal condensation of the carboxy group of N-methylanthranilic acid with methanol. It has a role as a fungal metabolite, a plant metabolite and an animal metabolite. It is a benzoate ester, a methyl ester, a secondary amino compound and a substituted aniline. It is functionally related to a N-methylanthranilic acid.

Preparation

By methylation of methyl anthranilate or esterification of N-methylanthranillic acid.

Taste threshold values

Taste 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 evaluation

The 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 Profile

Poison by intravenous route. Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.