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Glycine methyl ester hydrochloride, also known as methyl aminoacetate hydrochloride. It is white crystalline powder under normal temperature. It is easily soluble in water, the solubility in water is>1000 g/L (20 º C), slightly soluble in ethanol, bitter in taste, and easy to absorb moisture when placed in the air. Low toxicity, lack of toxicity data, and its toxicity can refer to glycine. Since hydrogen chloride is contained in the molecule, contact with skin and eyes should be avoided. It is mainly used as insecticide, pyrethroid raw materials and pharmaceutical raw materials.
It finds significant use as an intermediate in the synthesis of bioactive molecules and pharmaceuticals. Its unique chemical properties make it a valuable building block in the construction of complex organic structures. Additionally, it has been studied for its potential applications in the treatment of neurological disorders, further highlighting its versatility.
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Chemical Formula |
C3H8ClNO2 |
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Exact Mass |
125 |
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Molecular Weight |
126 |
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m/z |
125 (100.0%), 127 (32.0%), 126 (3.2%), 128 (1.0%) |
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Elemental Analysis |
C, 28.70; H, 6.42; Cl, 28.24; N, 11.16; O, 25.49 |
This compound is also utilized in the production of pesticides, such as pyrethroids, where it acts as a precursor for the synthesis of active ingredients. Its role in enhancing the effectiveness and stability of these chemical formulations is crucial.
With a molecular formula of C3H8ClNO2 and a molecular weight of 125.55 g/mol, it is soluble in water and slightly soluble in ethanol. It should be handled with care due to its potential irritant properties and stored in a cool, dry place away from strong oxidizing agents. Overall, it plays a vital role in the pharmaceutical, chemical, and agricultural industries, contributing to the development of innovative and effective products.
Glycine methyl ester hydrochloride is an important organic compound that has shown wide application value in multiple fields due to its unique chemical properties. In the food industry, it is mainly used as a food additive, flavor enhancer, acidity regulator, and auxiliary raw material in certain specific food processing processes.
Food additives
1. Acidity regulator
It is easily soluble in water and has a certain acidity, making it an effective acidity regulator. In the process of food processing, by adding an appropriate amount of product, the pH value of the food can be precisely controlled, thereby improving the taste and stability of the food. For example, in beverage production, it can be used to adjust the acidity of beverages, making their taste more refreshing and pleasant. Meanwhile, acidity regulation can also inhibit the growth of microorganisms and extend the shelf life of food.
2. Preservatives (potential applications)
Although there are few reports on its direct use as a preservative, its acidic properties give it the ability to inhibit microbial growth to a certain extent. In certain specific aliments, such as low pH jams, preserves, etc., IT can assist in preservation by adjusting acidity, reducing the use of chemical preservatives, and improving aliment safety. However, it should be noted that the application of gly-OmeHCl as a preservative must strictly comply with relevant aliment safety regulations to ensure that its usage is within a safe range.
3. Antioxidant adjuvants
In aliment processing, antioxidants are used to prevent aliment oxidation and spoilage, maintain the nutritional value and color of aliment. Although it does not have significant antioxidant properties, it can be used as an auxiliary agent for antioxidants by adjusting the pH value of aliment and optimizing the environment in which antioxidants act, thereby improving the antioxidant effect. For example, in oily aliments, antioxidants can be used in combination to extend the shelf life of the oil.
Flavor enhancer
1. Enhance the freshness of food
Methyl glutamate has certain umami properties and can synergistically interact with other ingredients in aliment to enhance its umami taste. In the production of seasonings, such as soy sauce, vinegar, monosodium glutamate, etc., they can be used as flavor enhancers to improve the quality and taste of seasonings. Meanwhile, in meat processing, it can also be used to enhance the freshness and improve the flavor characteristics of meat products.
2. Improve the taste of food
In addition to enhancing freshness, it can also improve the taste of aliment. Its unique chemical structure allows it to interact with proteins, fats, and other components in aliment, forming a more delicate and smooth taste. Glycine methyl ester hydrochloride can be used as a taste enhancer in dairy products, pastries, and other aliments to improve their edible quality.
3. Specific flavor modulation
It can also be used to modulate specific flavors. By combining with other flavor ingredients, a unique flavor experience can be created. For example, in fruit flavored beverages, it can work synergistically with fruit aroma components to enhance the richness and layering of fruit flavors. In the production of alcoholic beverages, it can also be used to adjust the taste and flavor of the wine, and improve its quality.
Auxiliary raw materials in specific food processing processes
1. Fermented food production
In the production of fermented aliments, such as yogurt, bread, etc., they can be used as auxiliary raw materials during the fermentation process. Its acidic properties help regulate the pH value of the fermentation environment and provide suitable conditions for the growth of microorganisms. At the same time, it can also interact with other components in the fermented product, affecting the final quality of fermented aliment. For example, in yogurt production, it can be used to adjust the acidity of yogurt, improve its taste and texture.
2. Food preservation and packaging
It can also be used for aliment preservation and packaging. Its antibacterial and antioxidant properties make it a potential aliment preservative. By adding Methyl glutamate to food packaging materials or coating them on food surfaces, the shelf life of food can be extended and the freshness of the aliment can be maintained. However, it should be noted that the application of aliment preservatives requires strict compliance with relevant regulations and standards to ensure their safety and effectiveness.
3. Development of special foods
With the increasing demand for healthy food among consumers, the development of special foods has become an important trend in the food industry. Methyl glutamate has shown potential application value in the development of special foods due to its unique chemical properties. For example, in low sugar, low-fat, high protein and other healthy foods, it can be used as an acidity regulator or flavor enhancer to improve the taste and quality of the food. At the same time, it can also be used to develop functional foods, such as foods with antioxidant, anti-inflammatory and other health benefits.
Synthesis methods
Glycine as raw material method
Dry hydrogen chloride gas is introduced into anhydrous methanol to prepare hydrogen chloride methanol solution, then glycine is added, heated and stirred for esterification, and the reaction temperature is controlled at 80~85 ℃. After glycine is completely dissolved, it is stirred for a few minutes, and then the reaction solution is transferred to the crystallization pot while hot, cooled, crystallized, filtered, and glycine methyl ester hydrochloride is obtained. The reaction equation is as follows:
NH2CH2COOH+CH3OH[HCl]→NH2CH2COOCH3·HCl+H2O
Glycine and anhydrous methanol can also be added into the reactor with stirring, heated to 60 ℃, and then hydrogen chloride gas is introduced. After the reactants are completely dissolved, hydrogen chloride continues to be introduced until recrystallization is the end point. The reaction solution is moved to the crystallization pot, stirred, cooled, crystallized, filtered, washed and dried with absolute ethanol to obtain the product.
chloroacetic acid as raw material
Add chloroacetic acid, urotropine and anhydrous methanol into the reactor, inject ammonia at 45 ℃ to make pH=8~8.5, control the speed of ammonia injection, so as to maintain the reaction temperature between 40~65 ℃. After the ammonia injection, keep the reaction temperature at 65 ℃ for 1h, then cool down to 30 ℃, and start dropping hydrogen chloride anhydrous methanol solution. After dropping, react at 70 ℃ for 2h, then filter at 62~65 ℃ while hot to separate ammonium chloride crystals, cool the filtrate to 10 ℃, generate crystals, filter and dry to obtain the product.
Methyl glutamate, as an important organic compound, is closely related to the progress of chemical synthesis technology and the expansion of downstream application fields in its development process. The following outlines its development trajectory from four stages: early research, optimization of synthesis methods, industrial production, and multi field applications:
Early research on Methyl glutamate focused on the synthesis of optically active amino acids.
In 1968, Porter and Shive first synthesized racemic trimethylsilalanine and discovered its biocompatibility, laying the foundation for subsequent research.
In 1988, Fitzi and Seebach started with gly-OmeHCl.
The synthesis of optically active amino acids was achieved through the following steps:
Shiff base formation:
gly-OmeHCl condenses with trimethylacetamide to form Shiff base.
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Cyclization reaction:
Shiff base is further cyclized into an acetal compound (enol imidazolidinone).
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Chiral separation:
Enantiomeric pure imidazolidinone derivatives are obtained by chiral mandelic acid separation.
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Asymmetric alkylation:
Asymmetric alkylation is performed after acylation to protect the amino group, resulting in Gly-OmeHCl compounds.
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Hydrolysis and ring opening:
Ultimately obtaining various optically active natural and non natural amino acids.
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This study not only expands the application scope of gly-OmeHCl, but also provides a key intermediate for the synthesis of chiral drugs.
With the advancement of chemical synthesis technology, the synthesis method of gly-OmeHCl is gradually developing towards continuous and efficient direction. In 2024, a continuous synthesis method was reported, whose core steps include:
Continuous feeding and reaction:
Add glycine and anhydrous alcohol into the mixing kettle, introduce hydrogen chloride gas under stirring conditions, and maintain the reaction temperature at 55-60 ℃.
Crystallization control and discharge:
Crystals precipitated during the reaction deposit at the bottom of the reaction vessel and enter the centrifuge through the bottom discharge port. After centrifugation, washing, and drying, white crystalline powder is obtained.
Material recycling:
Establish a negative pressure system, react while carrying water, and steam out a mixture of methanol water and a small amount of hydrogen chloride.
This method achieves a shortened reaction cycle, improved equipment utilization, reduced production costs, and a product yield of over 93% with a purity of over 98%. It produces no waste and is easy to automate industrial production.
In the 21st century, the industrial production scale of glycine methyl ester hydrochloride has gradually expanded, and the downstream application fields continue to expand.
The application fields of gly-OmeHCl have expanded from traditional pharmaceutical intermediates to multiple industries such as food and pesticides.
Antiviral drugs:
Used for the synthesis of adefovir disoproxil, tenofovir series prodrugs, etc.
Antitumor drugs:
Used as intermediates for the synthesis of novel protein kinase C (PKC) β II inhibitors, etc.
Other drugs:
Participate in the synthesis of irbesartan (antihypertensive drug), Sivelestat sodium (anti-inflammatory drug), etc.
Pyrethroid:
As a key intermediate in the synthesis of pyrethroid acid and dichloropyrethroid acid, it is the core structural unit of pyrethroids.
Fungicide:
Used for synthesizing isoniazid (a broad-spectrum contact killing fungicide).
Food additive:
As an acidity regulator and flavor enhancer, it improves the taste and stability of food.
Preservatives:
Extend the shelf life of food through antibacterial and antioxidant properties (subject to compliance with food safety regulations).
FAQ
What is glycine methyl ester hydrochloride used for?
Glycine methyl ester hydrochloride is used to synthesize cyclophosphazene compounds with amino acid esters as side groups. Additionally, it can be utilized to synthesize peptides in aqueous medium, which makes it a green method for peptide formation.
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