Methyl 2-Aminobenzoate
Methyl anthranilate
CAS: 134-20-3
Molecular Formula: C8H9NO2
Methyl 2-Aminobenzoate - Names and Identifiers
| Name | Methyl anthranilate |
| Synonyms | Methyl anthranilate Methl-O-Aminobenzoate Methyl 2-Aminobenzoate 2-amino-3-methylbenzoate Anthranilic acid methylester Anthranilic acid methyl ester 2-Aminobenzoic acid methyl ester |
| CAS | 134-20-3 |
| EINECS | 205-132-4 |
| InChI | InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3 |
| InChIKey | VAMXMNNIEUEQDV-UHFFFAOYSA-N |
Methyl 2-Aminobenzoate - Physico-chemical Properties
| Molecular Formula | C8H9NO2 |
| Molar Mass | 151.163 |
| Density | 1.166g/cm3 |
| Melting Point | 24℃ |
| Boling Point | 256°C at 760 mmHg |
| Flash Point | 112.9°C |
| Water Solubility | slightly soluble |
| Vapor Presure | 0.0158mmHg at 25°C |
| Appearance | Clear yellow-brown Liquid |
| pKa | pK1:2.23(＋1) (25°C) |
| PH | 7.5-8 (H2O, 20℃)Aqueous solution |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.565 |
| Physical and Chemical Properties | Appearance: White Crystal Melting Point: 24 ℃ Boiling Point: 256 ℃ |
| Use | For the synthesis of spices, drugs, etc |
Methyl 2-Aminobenzoate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 1 |
| RTECS | CB3325000 |
| FLUKA BRAND F CODES | 21 |
| 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) |
Methyl 2-Aminobenzoate - Upstream Downstream Industry
Methyl 2-Aminobenzoate - Nature
Open Data Verified Data
colorless to light yellow liquid, with blue fluorescence, with orange flower fruit aroma. Soluble in ethanol, ether and other organic solvents, water-soluble and glycerol.
Last Update：2024-01-02 23:10:35
Methyl 2-Aminobenzoate - Preparation Method
Open Data Verified Data
prepared by esterification of anthranilic acid with methanol under acidic conditions and neutralization by alkali. Or by phthalic anhydride by ammonification, degradation, esterification.
Last Update：2022-01-01 10:07:48
Methyl 2-Aminobenzoate - Use
Open Data Verified Data
for the preparation of grape, cherry, strawberry, watermelon, citrus and other food flavor and wine flavor. In chewing gum, the usage amount is 2200mg/kg; In candy, 56mg/kg; In pudding, 23mg/kg; In cold drinks, 21mg/kg; In baked food, 20mg/kg; In soft drinks, 16mg/kg; 0.2mg/kg in alcohol.
Last Update：2022-01-01 10:07:48
Methyl 2-Aminobenzoate - Security information
category flammable liquids
Toxicity grading poisoning
acute toxicity oral-rat LD50: 2910 mg/kg; Oral-mouse LD50: 3900 mg/kg
stimulation data skin-rabbit 500 mg/24 hours moderate
Flammable hazard characteristics are flammable; combustion produces toxic nitrogen oxide smoke
storage and transportation characteristics warehouse ventilation and low temperature drying
Fire extinguishing agent dry powder, foam, sand, carbon dioxide, mist water
Dangerous Goods Sign Xi
hazard category code 36/37/38
Safety instructions 26-36-37/39
WGK Germany 1
RTECS number CB3325000
F 21
autoignition temperature 986 °F
TSCA Yes
customs code 29224995
toxicity LD50 orally in rats, mice: 2910, 3900 mg/kg, p. m. Jenner et al., food cosmet. Toxicol. 2,327 (1964)
Last Update：2024-04-10 22:29:15
Methyl 2-Aminobenzoate - Uses and synthesis methods
background
Since the discovery of methyl anthranilate in neroli oil in 1899, people have successively found anthranilic acid esters in many natural plants such as oranges, lemon jasmine, ylang-ylang, gardenia, etc. The existence of compounds has attracted the attention of the spice industry. Anthranilates are both esters and primary aromatic amines, so they have the dual characteristics of esters and amines. When it is added to flavors containing other aldehydes, it can undergo condensation reaction with aldehydes to produce Sch base (Sch near Base) with more stable properties and stronger aroma.
application
Most Schiff bases have dark colors, but some are light orange and have a strong aroma, which is a good agent in essence. Because such compounds have strong fruit fragrance and flower fragrance, they have been widely used in daily flavor and edible flavor. In edible flavors, it is the main flavor of grape flavor, and can also be used in various berries, melons, honey flavors, citrus, roses, violets and wine flavors. Methyl anthranilate is one of the backbone products of the perfume industry. It can also prepare about 60 kinds of spices; menthyl anthranilate obtained by transesterification with menthol is an effective sunscreen agent.
Use
Methyl anthranilate orMethyl 2-aminobenzoate naturally exists in essential oils such as citrus, tuberose, jasmine, gardenia, orange blossom, etc. It has strong fruit and flower fragrance. It is one of the backbone products of the spice industry and is widely used in daily and edible flavors. In the edible flavor, it is the main flavor of grape flavor, and can also be used in various berry, melon, honey flavor, citrus, lemon, strawberry and pineapple. About 60 kinds of fragrances can also be prepared from methyl anthranilate. For example, other anthranilate esters prepared by transesterification reaction of methyl anthranilate are one of the commonly used raw materials for flavoring, with a wide range of uses and high value; It reacts with some aldehydes to form Schiff bases with more stable properties and stronger aroma. It is a good fixative in flavors.
Preparation
Using o-nitrotoluene as the starting material:
o-nitrotoluene is oxidized to o-nitrobenzoic acid, which is then ammoniated and converted into o-aminobenzoic acid. Finally, it reacts with methanol and catalyzes esterification with an acidic catalyst to obtain methyl anthranilate
content analysis
accurately weigh about 1.0g of sample and determine it according to method 1 in ester determination method (OT-18). The equivalent factor (e) in the calculation is 75.59.
Toxicity
ADI 0~1.5 mg/kg FAO/WHO,1994).
GRAS(FDA,& sect;182.60,2000).
LD50 2910mg/kg (rat, oral).
use limit
FEMA(mg/kg 1998 revision): baked products 38; Alcohol-free beverage 40; Alcohol-containing beverage 0.2~2.0; Gum sugar 200~1583; Frozen dairy 40; Fruit ice 40; Gel and pudding 20; Hard candy 80~161; Jam and jelly 6; Fudge 80.
Last Update：2024-04-09 21:01:54
Methyl 2-Aminobenzoate - Uses and synthesis methods
Use
methyl anthranilate is a food spice allowed by the hygienic standard for the use of food additives in China. it is used to prepare watermelon, citrus, grape, strawberry and other fruit flavor and wine flavor. The usage amount in chewing gum is 2200 mg/kg; 56 mg/kg in candy; 23 mg/kg in pudding; 21 mg/kg in cold drinks; 20 mg/kg in baked food; 16rng/kg in soft drinks; 0.2 mg/kg in alcohol.
this product can be used as an intermediate for pesticides and saccharin. Methyl anthranilate has the sweet fragrance of tower flowers, and has a grape-like fragrance when diluted. It is used for the blending of cheap artificial flower oils. It also uses soap spices or grape flavors. Our GB 2760-86 stipulates that edible spices are allowed to be used. It is mainly used to prepare flavors such as grapes, oranges, roganberries, strawberries and watermelons. Anthranilates can react with aldehydes to form valuable soap-based fragrances, such as hydroxyl aromatic aldehydes and anthranilate. The following spices are obtained by the action of methyl ester. This kind of spice is already commercially available in China, and the trade name is Aurantiol. The oral LD50 was 2910mg/kg in rats and 3900mg/kg in mice.
for organic synthesis
Used to synthesize spices, drugs, etc.
GB 2760 a 1996 stipulates that it is temporarily allowed to use edible spices. It is mainly used to prepare flavors such as grapes, citrus, luogan berries, strawberries and watermelons. It is also a necessary raw material for the preparation of artificial orange oil.
can be used to prepare jasmine, orange blossom, gardenia, narcissus, tuberose, white orchid, ylang ylang and other types of flavors. It is often shared with orange leaf oil in oriental fragrance, heavy floral fragrance, and sweet wood fragrance. In edible flavor, it is not only suitable for grape type, but also for berry, strawberry, watermelon, honey, citrus and other types. It is also available in wine flavors.
Production method
dissolve anthranilic acid in methanol with 5 times the volume, pass hydrogen chloride, saturate and place for 1h, then heat and reflux for 1h, evaporate excess methanol, add sodium hydroxide solution, and make it precipitate by steam distillation or vacuum distillation.
With the participation of sulfuric acid, the o-nitrobenzoic acid and methanol are esterified into methyl o-nitrobenzoate, and then reduced with stannous chloride in ethanol solution, neutralized with alkali, and then distilled by steam.
It is obtained by esterification of sodium o-benzamide formate, sodium hypochlorite, methanol, etc.
Production method
in nature, methyl anthranilate exists in tartar oil, neroli oil, ylang ylang, jasmine oil, tuberose oil, etc. Industrial manufacturing is generally obtained by esterification of anthranilic acid and methanol. The methanol solution of anthranilic acid was heated to 65 ℃, sulfuric acid was added dropwise, and the sulfate of methyl anthranilic acid was formed at 75 ℃. Then neutralize and precipitate methyl anthranilate with sodium hydroxide solution. After extracting with toluene, washing the toluene extract and evaporating toluene, the crude methyl anthranilate was subjected to vacuum distillation in the presence of sodium carbonate, and the finished fraction was cooled to below 12-15 ℃, I .e. methyl anthranilate was precipitated. Another preparation method is to obtain this product by ammonification, degradation and esterification of phthalic anhydride.
Production method
phthalic anhydride is added into ammonia water at 0 ℃, and the solution is completed within 1~2min. when the temperature rises to 48~50 ℃, sodium hydroxide solution at 5 ℃ is added, the temperature is controlled below 70 ℃, and the reaction solution remains alkaline. Ammonia was discharged at 60~65 ℃ for 10h to obtain sodium orthoformyl carbamobenzoate solution. Cool it to -12 ℃, add methanol at -10 ℃, add sodium hypochlorite solution at -10 ℃ under stirring, and maintain the reaction below 0 ℃ for 1h. Then the temperature is raised to about 20°C and tested with potassium iodide starch solution until it is colorless. Heat to 45 ℃ to dissolve it, transfer to the sedimentation tank and stand for 8h, separate out the mother liquor, take the oil layer and filter it, then stand for stratification to obtain methyl anthranilate with a yield of more than 90%.
Heat the methanol solution of anthranilic acid to 65°C, add sulfuric acid dropwise, and react at 75°C to produce sulfate of methyl anthranilic acid. After neutralization with sodium hydroxide, methyl anthranilate is precipitated, extracted with toluene, washed the toluene extract, and evaporated to remove toluene, and finally distilled under reduced pressure in the presence of sodium carbonate to obtain the finished product.
Last Update：2024-04-09 21:01:54
Methyl 2-Aminobenzoate - Nature
| melting point | 24°C (lit.) |
| boiling point | 256°C (lit.) |
| density | 1.168 g/mL at 25°C (lit.) |
| Vapor pressure | 1mm Hg ( 20 °C) |
| refractive index | n20/D 1.582(lit.) |
| FEMA | 2682 | METHYL ANTHRANILATE |
| flash point | 220 °F |
| storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | alcohol: freely soluble(lit.) |
| acidity coefficient (pKa) | pK1:2.23(+1) (25°C) |
| morphology | Liquid |
| color | Clear yellow-brown |
| Odor | grape odor |
| PH value | 7.5-8 (H2O, 20℃)Aqueous solution |
| explosion limit value (explosive limit) | 1.4-7.8%(V) |
| water solubility | slightly soluble |
| sensitivity | Air Sensitive |
| JECFA Number | 1534 |
| Merck | 14,6020 |
| BRN | 606965 |
| stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChIKey | VAMXMNNIEUEQDV-UHFFFAOYSA-N |
| NIST chemical information | Benzoic acid, 2-amino-, methyl ester(134-20-3) |
| EPA chemical information | Methyl anthranilate (134-20-3) |
Last Update：2024-04-09 19:04:55
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View History
Raw Materials for Methyl 2-Aminobenzoate
Sodium hypochlorite
Potassium iodide
Stannous chloride dihydrate
Anthranilic acid
Sodium chlorate
Sodium formate
Benzamide
Methyl benzoate
Neroli oil
PEANUT OIL
aminoformic acid
2-Nitrobenzoic acid
AminobenzoicAcid
Potassium iodide
Stannous chloride dihydrate
Anthranilic acid
Sodium chlorate
Sodium formate
Benzamide
Methyl benzoate
Neroli oil
PEANUT OIL
aminoformic acid
2-Nitrobenzoic acid
AminobenzoicAcid
Downstream Products for Methyl 2-Aminobenzoate
Saccharin
Bentazone
Methyl 2-(methylamino)benzoate
Pigment Red 175
Bromhexine hydrochloride
Methyl 2-amino-3,5-dibromobenzoate
2-AMINO-3,5-DIBROMOBENZYL ALCOHOL
1,2-benzisothiazol-3(2H)-one 1,1-dioxide, ammonium salt
Potassium saccharate
Bentazone
Methyl 2-(methylamino)benzoate
Pigment Red 175
Bromhexine hydrochloride
Methyl 2-amino-3,5-dibromobenzoate
2-AMINO-3,5-DIBROMOBENZYL ALCOHOL
1,2-benzisothiazol-3(2H)-one 1,1-dioxide, ammonium salt
Potassium saccharate