Chemical Properties
dark brown liquid
Chemical Properties
Butyl anthranilate has a sweet, faint, fruit (plum, petigrain) note.
Occurrence
Reported present in peppermint oil from Brazil, Achillea ageratum, tea and in apple aroma.
Preparation
Prepared by transesterification of methyl anthranilate (methyl 2-aminobenzoate) with n-butyl alcohol in the presence of HCl.
Definition
ChEBI: A benzoate ester obtained by formal condensation of the carboxy group of anthranilic acid with the hydroxy group of butanol. Found in several fruit species, it is used as a flavouring and fragrance agent and also exhibits insect repellent properties.
Taste threshold values
Taste characteristics at 50 ppm: floral, green, fruity, sweet citrus, waxy character.
General Description
Dark brown liquid. Insoluble in water.
Air & Water Reactions
Sensitive to air and light. Insoluble in water. BUTYL ANTHRANILATE will hydrolyze under high and low pH conditions. .
Reactivity Profile
BUTYL ANTHRANILATE is an aminophenyl ester derivative. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Fire Hazard
Flash point data for BUTYL ANTHRANILATE are not available. BUTYL ANTHRANILATE is probably combustible.
Metabolism
Esters of benzoic acid are presumably either hydrolysed and then metabolized according to the normal pattern for the alcohol and acid produced, or possibly in some cases the ring may be hydroxylated and the product excreted as a glucuronide or sulphate ester . H-Butanol and isobutanol are rapidly oxidized in vivo, presumably to the aldehyde and acid ; only small amounts were excreted by rabbits as the glucuronic acid conjugates
