Basic information Content analysis Chemical properties Amount of usage limit Application Preparation Category Toxic Toxicity Acute toxicity Flammability Hazardous characteristics Storage characteristics Fire extinguishing agent Safety Supplier Related
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Methyl anthranilate

Basic information Content analysis Chemical properties Amount of usage limit Application Preparation Category Toxic Toxicity Acute toxicity Flammability Hazardous characteristics Storage characteristics Fire extinguishing agent Safety Supplier Related

Methyl anthranilate Basic information

Product Name:
Methyl anthranilate
Synonyms:
  • NEROLI
  • NEROLI OIL, ARTIFICIAL
  • 2-AMINOBENZOIC ACID METHYL ESTER
  • ANTHRANILIC ACID METHYL ESTER
  • ANTHRANILIC ACID:METHYL ESTER
  • METHYL 2-ANTHRANILATE
  • METHYL 2-AMINOBENZOATE
  • Methl-O-Aminobenzoate
CAS:
134-20-3
MF:
C8H9NO2
MW:
151.16
EINECS:
205-132-4
Product Categories:
  • Building Blocks
  • C8 to C9
  • Benzene derivatives
  • Aromatic Esters
  • Aromatics
  • Carbonyl Compounds
  • CARBOXYLICESTER
  • pharmacetical
  • Chemical Synthesis
  • Citrus aurantium (Seville orange)
  • Esters
  • Nutrition Research
  • Flavor
  • Halogenated Heterocycles ,Pyrimidines
  • Organic Building Blocks
  • Phytochemicals by Plant (Food/Spice/Herb)
Mol File:
134-20-3.mol
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Methyl anthranilate Chemical Properties

Melting point:
24 °C(lit.)
Boiling point:
256 °C(lit.)
Density 
1.168 g/mL at 25 °C(lit.)
vapor pressure 
1 mm Hg ( 20 °C)
refractive index 
n20/D 1.582(lit.)
FEMA 
2682 | METHYL ANTHRANILATE
Flash point:
220 °F
storage temp. 
-20°C Freezer
solubility 
alcohol: freely soluble(lit.)
pka
pK1:2.23(+1) (25°C)
form 
Liquid
color 
Clear yellow-brown
Odor
grape odor
PH
7.5-8 (H2O, 20℃)Aqueous solution
explosive limit
1.4-7.8%(V)
Water Solubility 
slightly soluble
Sensitive 
Air Sensitive
JECFA Number
1534
Merck 
14,6020
BRN 
606965
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
VAMXMNNIEUEQDV-UHFFFAOYSA-N
CAS DataBase Reference
134-20-3(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid, 2-amino-, methyl ester(134-20-3)
EPA Substance Registry System
Methyl anthranilate (134-20-3)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
1
RTECS 
CB3325000
21
Autoignition Temperature
986 °F
TSCA 
Yes
HS Code 
29224995
Hazardous Substances Data
134-20-3(Hazardous Substances Data)
Toxicity
LD50 orally in rats, mice: 2910, 3900 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964)

MSDS

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Methyl anthranilate Usage And Synthesis

Content analysis

Accurately weigh about 1.0 g of the sample; determine the amount based on the ester assay (OT-18). The equivalent factor (e) in the calculation takes 75.59.

Chemical properties

It appears as colorless to pale yellow liquid; it has blue fluorescence with orange blossom aroma. It has a freezing point of 24 °C with a boiling point of 273 ° C and a temperature of 132 ° C (1.87 kPa). It is soluble in ethanol, ether and other organic solvents, slightly soluble in water and glycerol. Rat oral LD50:2910mg/kg, Adl 0~1.5mg/kg (FAO/WHO1994).

Amount of usage limit

FEMA (mg/kg 1998 revised): baked goods 38; no alcohol drinks 40; alcoholic beverages 0.2 to 2.0; gums 200 to 1583; frozen dairy products 40; fruit ice 40; gel, pudding 20; 80~161; jam, jelly 6; soft candy 80.

Application

  • O-aminobenzoic acid methyl ester is allowable food spices as provided in the "food additives use health standards" in China. It can be used for the preparation of watermelon, citrus, grapes, strawberries and other fruit flavor and wine flavor. Its usage amount in chewing gum is 2200mg/kg; in candy, it is 56mg/kg; in pudding, it is 23 mg/kg; cold drink: 21mg/kg; baking food: 20mg/kg; soft drinks: 16rng/kg; alcohol: 0.2mg/kg.
  • This product can be used as intermediates of pesticide and saccharin. Methyl anthranilate has a sweet aroma of towers and have a grape-like flavor upon dilution. It can be used for the blend of cheap artificial flower oil as well as for soap spice or grape flavor. China GB 2760-86 provides it as allowable food spices. It is mainly used to prepare grapes, citrus, rosley, strawberries and watermelon and other flavor. Anthranilates can react with aldehyde to produce valuable soap-based spices. For example, hydroxy aromatic aldehyde can react with the methyl anthranilate to obtain the following spices. This kind of fragrance has a commercially available product under the trade name Aurantiol. Rat-oral has a LD50: 2910mg /kg; for mice, it is 3900mg/kg.
  • Used for organic synthesis
  • Used for the synthesis of spices, drugs and so on.
  • GB 2760-1996 provides it as temporarily allowable food spices. It is mainly used to prepare grapes, citrus, rosley, strawberries and watermelon and other types of flavor, but also as the raw materials for the preparation of artificial orange oil.
  • It can be used to prepare flavors of jasmine, orange blossom, gardenia, narcissus, tuberose, white orchid and ylang. It is often used in combination with orange leaf oil in the oriental flavor, heavy flower type and sweet wood type. In the edible flavor, it is not only suitable for grape type, but also for berries, strawberries, watermelon, honey, citrus and other types. It can also be used in wine flavor.

Preparation

Dissolve the anthranilic acid in 5 times the volume of methanol; send into hydrogen chloride; stand 1 h after saturation; then heat to reflux 1h; steam the excess amount of methanol, add sodium hydroxide solution, make it precipitated and obtain the final product through steam distillation or vacuum distillation.
In the presence of sulfuric acid, the o-nitrobenzoic acid and methanol are subject to esterification to generate o-nitrobenzoic acid methyl ester, and then reduced by stannous chloride in ethanol solution, neutralized with alkali and then subject to steam distillation to  derive it.
It can be obtained through the esterification of o-benzoyl formate sodium, sodium hypochlorite and methanol.
In nature, o-aminobenzoic acid methyl ester exists in the tower flower oil, orange blossom oil, ylang, jasmine oil, tuberose oil and so on. Industrial manufacturing is generally achieved by esterification of o-aminobenzoic acid with methanol. The anthranilic acid methanol solution was heated to 65 ° C; add drop wise of sulfuric acid, and generate the sulfate of methyl anthranilate upon reaction at 75 °C. Then neutralize with sodium hydroxide solution to precipitate methyl anthranilate. After extraction with toluene, the toluene extract is washed and the toluene is distilled off. The crude o-aminobenzoate is subjected to vacuum distillation under the conditions of sodium carbonate. The finished fraction is cooled to below 12-15 ° C so that the methyl anthranilate is precipitated out. Another method is by the phthalic anhydride by ammoniation, degradation and esterification to obtain this product.
To the 0 ℃ of ammonia, add phthalic anhydride within 1~2 min. When the temperature rose to 48~50 ℃, add 5 ℃ sodium hydroxide solution; control the temperature at 70 ℃ so that the reaction liquid is maintained alkaline. Under the 60~65 ℃, drain the ammonia for 10 h to obtain the sodium o-formamidobenzoate solution. The mixture was cooled to-12 °C; methanol was added at-10 °C, and a solution of sodium hypochlorite at-10 ° C was added with stirring, and the mixture was allowed to react at 0 °C for 1 hour. And then heat to about 20 ℃. Use potassium iodide starch solution to test until a colorless reaction is reached. Heat to 45 °C to dissolve, transfer into the sedimentation tank for 8h, separate out the mother liquor, take the oil layer for filtration and then stand for layering to obtain the o-aminobenzoic acid methyl ester with the yield of 90% or more.

Category

Flammable liquids

Toxic

grading poisoning

Toxicity

ADI 0~1.5 mg/kg FAO/WHO, 1994);
GRAS (FDA, § 182.60, 2000);
LD50: 2910mg/kg (rat, oral);

Acute toxicity

oral-rat LD50: 2910 mg/kg; oral-mouse LD50: 3900 mg/kg
Stimulate Data Skin-Rabbit 500 mg/24 h moderate

Flammability Hazardous characteristics

Flammable; combustion produces toxic nitrogen oxide fumes

Storage characteristics

warehouse ventilated, low temperature and dry.

Fire extinguishing agent

dry powder, foam, sand, carbon dioxide, mist water.

Description

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.

Chemical Properties

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).

Chemical Properties

Methyl anthranilate has a characteristic orange-flower odor and a slightly bitter, pungent taste. May be prepared by heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.

Chemical Properties

Methyl anthranilate has a characteristic orange-flower odor and slightly bitter, pungent taste.

Chemical Properties

yellow to orange liquid with a smell of orange blossom

Occurrence

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.

Uses

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.

Uses

A useful synthetic intermediate.

Uses

As perfume for ointments; manufacture of synthetic perfumes.

Definition

ChEBI: A benzoate ester that is the methyl ester of anthranilic acid.

Preparation

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

Aroma threshold values

Detection: 3 ppb

Taste threshold values

Taste characteristics at 25 ppm: sweet, fruity, concord grape, with a musty and berry nuance.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 3599, 1992 DOI: 10.1016/S0040-4039(00)92512-7

General Description

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

Air & Water Reactions

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

Reactivity Profile

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.

Fire Hazard

Methyl anthranilate is combustible.

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.

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.

Metabolism

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

Toxicity evaluation

Even though MA is palatable to humans, it is an irritant to birds. The bird-repellent properties of MA and related compounds were discovered in the late 1950s (25). The mode of action is via the trigeminal nerve. Thus, all avian species tested so far perceive MA as an irritant, not as a taste repellent per se.

Methyl anthranilateSupplier

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Product Name:NEROLI
CAS:134-20-3
Purity:99%
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Product Name:Methyl anthranilate
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Product Name:Methyl anthranilate
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Product Name:Methylanthranilate
CAS:134-20-3
Purity:99% HPLC Package:25KG;200KG;5KG;1KG;1T Remarks:134-20-3