ChemicalBook > CAS DataBase List > Methyl anthranilate

Methyl anthranilate

Product Name
Methyl anthranilate
CAS No.
134-20-3
Chemical Name
Methyl anthranilate
Synonyms
METHYL 2-AMINOBENZOATE;Methyl antranilate;NEROLI;Nevoli oil;Methyl anthranylate;o-Carbomethoxyaniline;ANTHRANILIC ACID METHYL ESTER;2-amino-benzoicacimethylester;2-AMINOBENZOIC ACID METHYL ESTER;FEMA 2682
CBNumber
CB0722306
Molecular Formula
C8H9NO2
Formula Weight
151.16
MOL File
134-20-3.mol
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Methyl anthranilate Property

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
Odor Type
fruity
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
LogP
1.88 at 20℃
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

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
1
RTECS 
CB3325000
F 
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W268224
Product name
Methyl Anthranilate
Purity
natural, ≥98%, FG
Packaging
25g
Price
$108
Updated
2024/03/01
Sigma-Aldrich
Product number
W268224
Product name
Methyl Anthranilate
Purity
natural, ≥98%, FG
Packaging
100g
Price
$323
Updated
2024/03/01
Sigma-Aldrich
Product number
W268224
Product name
Methyl Anthranilate
Purity
natural, ≥98%, FG
Packaging
1kg
Price
$1830
Updated
2024/03/01
Sigma-Aldrich
Product number
W268208
Product name
Methyl Anthranilate
Purity
≥98%, FCC, FG
Packaging
sample-k
Price
$54.6
Updated
2024/03/01
Sigma-Aldrich
Product number
W268208
Product name
Methyl Anthranilate
Purity
≥98%, FCC, FG
Packaging
1kg
Price
$70.9
Updated
2024/03/01
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Methyl anthranilate Chemical Properties,Usage,Production

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.

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.

Definition

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.

Preparation

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

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.

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".

Metabolism

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.

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

Stannous chloride dihydrate Sodium benzoate Methanol solution Sodium hypochlorite Potassium iodide JasMine Oil PEANUT OIL Benzamide aminoformic acid Sodium formate Sodium chlorate Methyl benzoate Neroli oil Anthranilic acid 2-Nitrobenzoic acid AminobenzoicAcid

Preparation Products

2-AMINO-3,5-DIBROMOBENZYL ALCOHOL Methyl 2-amino-3,5-dibromobenzoate Saccharin sodium dihydrate Saccharin Methyl 2-(methylamino)benzoate 1,2-benzisothiazol-3(2H)-one 1,1-dioxide, ammonium salt Pigment Red 175 Bromhexine hydrochloride AZINPHOS-ETHYL SACCHARIN SODIUM SALT DIHYDRATE Bentazone Potassium saccharate Ambroxol CALCIUM SACCHARIN Methyl 2-(chlorosulfonyl)benzoate
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View Lastest Price from Methyl anthranilate manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Methyl Anthranilate 134-20-3
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-16
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Methl-O-Aminobenzoate 134-20-3
Price
US $60.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-05-16
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Methyl anthranilate 134-20-3
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-12

134-20-3, Methyl anthranilateRelated Search:

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