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134-20-3

134-20-3 Structure

134-20-3 Structure
IdentificationMore
[Name]

Methyl anthranilate
[CAS]

134-20-3
[Synonyms]

2-AMINOBENZOIC ACID METHYL ESTER
ANTHRANILIC ACID METHYL ESTER
ANTHRANILIC ACID:METHYL ESTER
FEMA 2682
LABOTEST-BB LTBB000479
METHYL 2-AMINOBENZOATE
METHYL 2-ANTHRANILATE
METHYL ANTHRANILATE
METHYL O-AMINOBENZOATE
NEROLI
NEROLI OIL, ARTIFICIAL
2-(Methoxycarbonyl)aniline
2-amino-benzoicacimethylester
2-Carbomethoxyaniline
Benzoicacid,2-amino-,methylester
Carbomethoxyaniline
Methyl anthranylate
Methyl ester of o-Aminobenzoic acid
Methylaminobenzoate
Methylester kyseliny anthranilove
[EINECS(EC#)]

205-132-4
[Molecular Formula]

C8H9NO2
[MDL Number]

MFCD00007710
[Molecular Weight]

151.16
[MOL File]

134-20-3.mol
Chemical PropertiesBack Directory
[Appearance]

yellow to orange liquid with a smell of orange blossom
[Melting point ]

24 °C (lit.)
[mp ]

24 °C(lit.)
[Boiling point ]

256 °C (lit.)
[bp ]

256 °C(lit.)
[density ]

1.168 g/mL at 25 °C(lit.)
[vapor pressure ]

1 mm Hg ( 20 °C)
[FEMA ]

2682
[refractive index ]

n20/D 1.582(lit.)
[Fp ]

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
[Stability:]

Stable. Combustible. Incompatible with strong oxidizing agents.
[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
[Merck ]

14,6020
[JECFA Number]

1534
[Detection Methods]

GC,NMR
[BRN ]

606965
[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)
[Storage Precautions]

Light sensitive
[EPA Substance Registry System]

134-20-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

1
[RTECS ]

CB3325000
[F ]

21
[Autoignition Temperature]

986 °F
[TSCA ]

Yes
[HS Code ]

29224995
[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.
[Hazardous Substances Data]

134-20-3(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Sodium hypochlorite-->Potassium iodide-->Stannous chloride dihydrate-->Anthranilic acid-->Sodium chlorate-->Sodium formate-->Sodium benzoate-->Benzamide-->Methyl benzoate-->Neroli oil-->JasMine Oil-->PEANUT OIL-->aminoformic acid-->2-Nitrobenzoic acid-->AminobenzoicAcid
【Preparation Products】

Saccharin-->Methyl 2-(chlorosulfonyl)benzoate-->Ambroxol-->Bentazone-->Saccharin sodium dihydrate-->SACCHARIN SODIUM SALT DIHYDRATE-->Methyl 2-(methylamino)benzoate-->Pigment Red 175-->Bromhexine hydrochloride-->Methyl 2-amino-3,5-dibromobenzoate-->CALCIUM SACCHARIN-->2-AMINO-3,5-DIBROMOBENZYL ALCOHOL-->1,2-benzisothiazol-3(2H)-one 1,1-dioxide, ammonium salt-->Potassium saccharate-->AZINPHOS-ETHYL-->METHYL BIPHENYL-2-CARBOXYLATE-->2,2'-IMINODIBENZOIC ACID
Hazard InformationBack Directory
[General Description]

Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence.
[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.
[Air & Water Reactions]

This compound is sensitive to air and light. Slightly water soluble .
[Fire Hazard]

This chemical is combustible.
[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.
[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]

As perfume for ointments; manufacture of synthetic perfumes.
[Uses]

A useful synthetic intermediate.
[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.
[Definition]

ChEBI: A benzoate ester that is the methyl ester of anthranilic acid.
[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
[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.
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Methyl anthranilate(134-20-3).msds
Questions And AnswerBack Directory
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl anthranilate(134-20-3) MS
Methyl anthranilate(134-20-3) 13C NMR
Methyl anthranilate(134-20-3) 1H NMR
Methyl anthranilate(134-20-3) ESR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Methyl anthranilate(134-20-3)
[Alfa Aesar]

Methyl anthranilate, 99%(134-20-3)
[Sigma Aldrich]

134-20-3(sigmaaldrich)
[TCI AMERICA]

Methyl Anthranilate,>99.0%(GC)(134-20-3)
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