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Methyl anthranilate

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? (1) ??? : ? ??? ???? 23.8℃????? ??.

??(2) ?? : ? ?? 1mL? 30℃? ???? ?? ?? 60% ??? 6mL? ?? ?, ? ?? ????? ??.

??(3) ??? : ? ??? ??? ? 1.582～1.584??? ??.

??(4) ?? : ? ??? ??? ????? ? ?????? ?? ??? ?, 1 ????? ??.

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? (1) ? ?? 0.1g? ??(1→10)? ??? ???????? 1mL ? β-??? 0.1g? ???????? 5mL? ?? ? 2mL? ??? ???? ??? ???.

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? ? ?? 0.5g? ??? ?? ????? ? ????? ? ?????????? ?? ????.

0.5N ?????????? 1mL ＝ 75.58mg C₈H₉NO₂

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Methyl anthranilate, also known as MA, methyl 2-amino benzoate or carbo methoxy aniline, is an ester of anthranilic acid. Its chemical formula is C₈H₉NO₂.

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Methyl Anthranilate occurs in a large number of blossom essential oils (e.g., neroli, ylang-ylang, and jasmine oils), grapes, and citrus oils. It occurs as white crystals (mp 24–25°C), or a yellowish liquid, that show blue fluorescence and have an orange blossom odor. Methyl anthranilate is prepared by esterification of anthranilic acid with methanol or by reaction of isatoic anhydride with methanol.
It is used in a large number of blossom fragrances. However, its use in perfumes for soaps and cosmetics is limited because it causes discoloration. It is used in flavor compositions (e.g., in grape and citrus flavors).

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Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes or hybrids thereof, and in bergamot, black locust, champaca , gardenia, jasmine, lemon, mandarin, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate.It is also secreted by the musk glands of foxes and dogs, and lends a "sickly sweetness" to the smell of rotting flesh.

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Methyl anthranilate acts as a bird repellent. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and golf courses. Dimethyl anthranilate (DMA) has a similar effect. It is also used for the flavor of grape Kool Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs.
Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery . It is also used to produce Schiff's Bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol - produced by combining methyl anthranilate and hydroxyl citronellal.

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ChEBI: Methyl anthranilate is a benzoate ester that is the methyl ester of anthranilic acid. It has a role as a metabolite and a flavouring agent. It derives from an anthranilic acid.

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By heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.

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Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence.

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Methyl anthranilate is sensitive to air and light. Slightly water soluble .

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An amine and ester. 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.

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Methyl anthranilate is combustible.

Toxicology

Methyl anthranilate is a colorless liquid that has a sweet, fruity, grape-like flavor. It is found in the essential oils of orange, lemon, and jasmine and has been widely used to create imitation Concord grape flavor. Table 10.8 shows the acute toxicity of methyl anthranilate. Methyl anthranilate promotes some allergic reactions on human skin, which has led to it being prohibited for use in cosmetic products.

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. A skin irritant. See also ESTERS. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx.

Safety

Methyl anthranilate is a plant-based compound with a long history of use as a flavor additive for foods and  beverages, and as an aromatic used extensively in perfumery. As such,  the US Department of Agriculture (USDA) and the Food and Drug  Administration (FDA) have approved MA as "generally recognized as safe".

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It is probable that this ester is hydrolysed and the anthranilate is excreted mostly as oaminobenzoyl glucuronide (Charconnet-Harding, Dalgliesh & Neuberger, 1953).

Solubility in organics

Methyl anthranilate is soluble in ethanol and propylene glycol. It is insoluble in paraffin oil.

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