A. Methyl Anthranilate
Synonyms Neroli Oil (Artificial).
Chemical Structure 2-Aminobenzoic acid methyl ester, (C8H9NO2).
17 ml of distilled water. The resulting methyl anthranilate sulphate thus obtained gets crystallized in the cold, which may be further purified by recrystallization from alcohol. Finally the pure desired ester is regenerated by treatment with dilute NaOH solution (2 N) carefully.
Characteristic Features It is a crystalline mass having a powerful pleasant taste. It has a peculiar odour that mostly resembles to orange blossoms and certain varieties of grape. It gives an inherent blue-violet fluorescence which is distinctly visible in any volatile oil containing it. Methyl anthranilate has the following physical parameters, namely: d 1.168; mp 24-25°C; bp15 135.5°C.
It is slightly soluble in water, but freely soluble in ethanol and ether.
Identification It may be identified by preparing its derivatives, such as: Picrate (mp 104°C); Benzoate (mp 100°C).
Uses
1. It is used frequently as a perfume for ointments.
2. It is also employed for the manufacture of synthetic perfumes.
Occurrence It occurs in a good number of medicinal herbs, for instance: Flowers of Robinia pseudoacacia L. (Family: Fabaceae)-Black Locust, False Acacia; Citrus sinensis (Linn.) Osbeck. (Family: Rutaceae)-Sweet Orange; Cananga odorata (Lam.) Hook. f. & Thoms. (Family:
Annonaceae)-Ylang-Ylang, Cananga; Jasminum officinale Linn. var grandiflorum Bailey., (Family: Oleaceae)-Jasmine. It is also found in bergamot, other essential oils and in grape juice. It is also obtained synthetically by carrying out the esterification of anthranilic acid with methanol in the presence of HCl.
Isolation Methyl anthranilate may be isolated from the essential oils very conveniently by shaking the volatile oil with cold dilute sulphuic acid (2 N) i.e., 1 ml of conc. H2SO4 dissolved slowly in
17 ml of distilled water. The resulting methyl anthranilate sulphate thus obtained gets crystallized in the cold, which may be further purified by recrystallization from alcohol. Finally the pure desired ester is regenerated by treatment with dilute NaOH solution (2 N) carefully.
Characteristic Features It is a crystalline mass having a powerful pleasant taste. It has a peculiar odour that mostly resembles to orange blossoms and certain varieties of grape. It gives an inherent blue-violet fluorescence which is distinctly visible in any volatile oil containing it. Methyl anthranilate has the following physical parameters, namely: d 1.168; mp 24-25°C; bp15 135.5°C.
It is slightly soluble in water, but freely soluble in ethanol and ether.
Identification It may be identified by preparing its derivatives, such as: Picrate (mp 104°C); Benzoate (mp 100°C).
Uses
1. It is used frequently as a perfume for ointments.
2. It is also employed for the manufacture of synthetic perfumes.
