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.
Uses
Methyl 2-(Methylamino)benzoate is one of many volatile components from mango cultivars.
Uses
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.
Preparation
By methylation of methyl anthranilate or esterification of N-methylanthranillic 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.
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 LD
50 value in rats was reported as 3.7 ml/kg (Levenstein, 1974). The acute oral LD
50 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 LD
50 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.
