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Methyl anthranilate

Content analysis Chemical properties Amount of usage limit Application Preparation Category Toxic Toxicity Acute toxicity Flammability Hazardous characteristics Storage characteristics Fire extinguishing agent
Methyl anthranilate
Methyl anthranilate structure
CAS No.
134-20-3
Chemical Name:
Methyl anthranilate
Synonyms
NEROLI;FEMA 2682;Nevoli oil;2-AMinobenzoic;Methyl antranilate;Methyl anthanilate;methyl anthranlate;METHYL ANTHRANILATE;Carbomethoxyaniline;Methyl anthranylate
CBNumber:
CB0722306
Molecular Formula:
C8H9NO2
Formula Weight:
151.16
MOL File:
134-20-3.mol

Methyl anthranilate 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. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
alcohol: freely soluble(lit.)
form 
Liquid
pka
pK1:2.23(+1) (25°C)
color 
Clear yellow-brown
PH
7.5-8 (H2O, 20℃)Aqueous solution
Odor
grape odor
explosive limit
1.4-7.8%(V)
Water Solubility 
slightly soluble
Sensitive 
Air Sensitive
Merck 
14,6020
JECFA Number
1534
BRN 
606965
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
VAMXMNNIEUEQDV-UHFFFAOYSA-N
CAS DataBase Reference
134-20-3(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
METHYL ANTHRANILATE
FDA 21 CFR
182.60; 582.60
EWG's Food Scores
1
FDA UNII
981I0C1E5W
NIST Chemistry Reference
Benzoic acid, 2-amino-, methyl ester(134-20-3)
EPA Substance Registry System
Methyl anthranilate (134-20-3)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H303
Precautionary statements  P280g-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
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
Toxicity LD50 orally in rats, mice: 2910, 3900 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964)
NFPA 704
1
1 0

Methyl anthranilate price More Price(21)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W268208 Methyl anthranilate ≥98%, FCC, FG 134-20-3 sample-k $50 2021-03-22 Buy
Sigma-Aldrich W268208 Methyl anthranilate ≥98%, FCC, FG 134-20-3 1 kg $63 2021-03-22 Buy
Sigma-Aldrich 236454 Methyl 2-aminobenzoate ReagentPlus , ≥99% 134-20-3 50g $77 2021-03-22 Buy
Sigma-Aldrich W268208 Methyl anthranilate ≥98%, FCC, FG 134-20-3 5 kg $181 2021-03-22 Buy
Sigma-Aldrich W268224 Methyl anthranilate natural, ≥98%, FG 134-20-3 25 g $190 2021-03-22 Buy

Methyl anthranilate Chemical Properties,Uses,Production

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

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 anthranilate Preparation Products And Raw materials

Raw materials

Preparation Products


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View Lastest Price from Methyl anthranilate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-09-17 Methyl 2-aminobenzoate
134-20-3
US $85.00 / KG 1KG 99% 10kg Hong Kong Tiansheng New Material Trading Co., Ltd
2021-09-09 Methyl 2-aminobenzoate
134-20-3
US $85.00 / KG 1KG 99% 100KG Hong Kong Tiansheng New Material Trading Co., Ltd
2021-09-07 Methyl anthranilate
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US $0.00 / Kg/Drum 1KG 99.9% 100000kg per month Wuhan Mulei New Material Technology Co. Ltd

Methyl anthranilate Spectrum


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