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Boc-L-aspartic Acid 1-benzyl Ester , also known as Boc Asp OBzl, CAS 30925-18-9, molecular formula C16H21NO6, molecular weight 323.341, usually exists in the form of white to almost white powder. Its application value as an intermediate in drug synthesis, energy supplement, organic synthesis raw material, catalyst carrier, and biological activity research has been widely recognized. As an important organic compound, it has wide applications in fields such as medicine, chemical industry, biotechnology, etc.
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Chemical Formula |
C16H21NO6 |
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Exact Mass |
323 |
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Molecular Weight |
323 |
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m/z |
323 (100.0%), 324 (17.3%), 325 (1.4%), 325 (1.2%) |
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Elemental Analysis |
C, 59.43; H, 6.55; N, 4.33; O, 29.69 |
Boc-L-aspartic Acid 1-benzyl Ester , as a derivative of aspartic acid, has a chemical formula of C16H21NO6 and a CAS number of 30925-18-9. It has unique chemical properties and wide application value. Boc-L-aspartate 1-benzyl ester plays an important role in fields such as medicine, chemical engineering, and biotechnology.
Applications in the field of medicine
(1) Drug synthesis intermediates
Boc-L-aspartate 1-benzyl ester serves as an important intermediate in drug synthesis and can react with other compounds to synthesize compounds with specific pharmacological effects. This characteristic makes it have broad application prospects in the field of drug development.
(2) Energy supplements
In vitro studies have shown that amino acids and their derivatives have been commercialized as energy supplements. Boc-L-aspartate 1-benzyl ester, as one of them, can affect the secretion of synthetic metabolic hormones, fuel supply during exercise, and mental performance during stress related tasks, and has a positive effect on improving exercise performance.
Applications in the field of chemical engineering
(1) Organic synthesis raw materials
Boc-L-aspartate 1-benzyl ester has a wide range of applications in the field of organic synthesis. It can be used as a raw material to participate in various organic synthesis reactions and prepare compounds with specific structures and properties. These compounds have important application value in fields such as medicine, pesticides, dyes, etc.
(2) Catalyst support
Boc-L-aspartate 1-benzyl ester has good stability and reactivity, and can be used as a carrier for catalysts to catalyze various organic synthesis reactions. By combining with other catalysts, the efficiency and selectivity of the reaction can be improved, and production costs can be reduced.
Applications in the field of biotechnology
Biological activity research-Boc-L-aspartate 1-benzyl ester plays an important role in biological activity research. By studying its biological activity, we can further understand its metabolic pathways and mechanisms of action in organisms, providing a theoretical basis for drug development and biotechnology applications.
Protein synthesis and modification-As an amino acid derivative, Boc-L-aspartate 1-benzyl ester can participate in protein synthesis and modification processes. By introducing it into proteins, the structure and function of proteins can be altered, thereby achieving regulation of protein properties. This characteristic has broad application prospects in the field of protein engineering.
Application in the field of cosmetics
Application in moisturizing cosmetics-It may exert moisturizing effects through multiple mechanisms. On the one hand, its molecular structure may contain hydrophilic groups that can form hydrogen bonds with water molecules, thereby adsorbing and retaining water. When applied to the surface of the skin, it can increase the moisture content of the stratum corneum, keeping the skin moist. On the other hand, it may help repair and strengthen the skin's barrier function. The normal functioning of the skin barrier is crucial for preventing water loss, and Boc-Laspartic Acid 1-benzyl Ester may promote the repair and reconstruction of the skin barrier by interacting with lipids or proteins in the skin, reducing water evaporation.
Boc-L-aspartic Acid 1-benzyl Ester may be added to some moisturizing face cream, lotion and essence.For example, a brand of moisturizing face cream contains hyaluronic acid, ceramide, etc. in addition to it. This face cream can quickly replenish moisture for the skin after use, and keep the skin moist for a long time to reduce the occurrence of dry skin, peeling and other phenomena.
Application in whitening cosmetics-May exert whitening effects by inhibiting the production of melanin.The generation of melanin is a complex biochemical process involving multiple enzymes and signaling pathways. Boc-Laspartic Acid 1-benzyl Ester may interfere with certain key processes, such as inhibiting tyrosinase activity.
Tyrosinase is a key enzyme in the process of melanin production, and inhibiting its activity can reduce melanin synthesis, thereby achieving whitening effects. In addition, it may also promote the metabolism and excretion of melanin, accelerate the breakdown and clearance of existing melanin in the skin, and gradually make the skin fair.Boc-L-aspartic Acid 1-benzyl Ester, vitamin C and nicotinamide were added to a whitening essence. After being used for a period of time, this essence can obviously improve the dull phenomenon of the skin, making the skin more bright and shiny.
At the same time, it also has a certain effect of uniform skin tone, reducing the appearance of pigmentation and freckles.
Application in repairing cosmetics-After being affected by external environmental stimuli, UV damage, or cosmetic allergies, the skin may experience impaired barrier function, inflammatory reactions, and other issues. Boc-Laspartic Acid 1-benzyl Ester may improve these issues by promoting the regeneration and repair of skin cells. It can stimulate the proliferation and differentiation of skin cells, accelerating the healing process of damaged skin.
In addition, it may also have anti-inflammatory effects, reducing skin inflammation and relieving discomfort symptoms such as redness, swelling, and itching.
This, ceramide and Centella asiatica extract were added to a repair facial mask. This facial mask is suitable for people with sensitive and damaged skin.
After use, it can quickly relieve skin discomfort and promote skin repair and regeneration.
Long term use can improve skin sensitivity and enhance skin tolerance.
Food developed to improve cognitive function
In some elderly nutritional supplements, Boc-Laspartic Acid 1-benzyl Ester is used in combination with other cognitive enhancing ingredients such as phosphatidylserine and DHA.
Clinical trials have found that elderly people who consume this supplement for a long time have improved performance in cognitive tests.
With the increase of incidence rate of metabolic diseases such as diabetes, the demand for food to regulate blood sugar is increasing.
Boc-Laspartic Acid 1-benzyl Ester may have the potential to regulate blood sugar.
Some experimental studies suggest that it may regulate blood glucose levels by affecting insulin secretion or its mechanism of action. The compound is added to some special foods for diabetes patients, such as low sugar biscuits, sugar free drinks, etc.
For example, Boc-L-aspartic Acid 1-benzyl Ester is added to a low sugar biscuit. After the eating test of diabetes patients, it is found that the biscuit has little effect on blood sugar after eating, which is helpful for diabetes patients to control blood sugar.
Application in Food Flavor Improvement-Boc-Laspartic Acid 1-benzyl Ester has certain flavor characteristics that can enhance the freshness and sweetness of food. Adding this compound to seasonings, soups, and other foods can enhance the overall flavor of the food. For example, adding an appropriate amount of Boc-Laspartic Acid 1-benzyl Ester to chicken essence seasoning can make the freshness and taste of chicken essence more rich. Consumers who use chicken essence with this compound added during cooking can clearly feel the enhanced flavor of the dish.
In addition to enhancing flavor, Boc-Laspartic Acid 1-benzyl Ester can also improve the taste of food. In some beverages, it can increase the richness and smoothness of the drink. For example, adding this compound to fruit juice drinks can make the taste of the juice softer and reduce its sourness.
Meanwhile, in some dairy products such as yogurt, cheese, etc., adding Boc-Laspartic Acid 1-benzyl Ester can improve the texture and taste of dairy products, making them more delicate and refreshing.
Application examples in food preservation-Food is prone to oxidation reactions during storage and processing, leading to food spoilage, nutrient loss, and flavor changes. Boc-Laspartic Acid 1-benzyl Ester has certain antioxidant activity, which can scavenge free radicals and delay the oxidation process of food. In some foods with high oil content, such as fried foods, nuts, etc., adding this compound can extend the shelf life of the food. For example, in potato chip production, adding Boc-Laspartic Acid 1-benzyl Ester can effectively prevent oxidation and rancidity of potato chips during storage, maintaining their crispy texture and original flavor.
Microbial contamination is one of the main causes of food spoilage. Boc-Laspartic Acid 1-benzyl Ester may have certain antibacterial effects, which can inhibit the growth and reproduction of certain microorganisms. Adding this compound to some fresh foods, such as meat, seafood, etc., can reduce the number of microorganisms and extend the shelf life of the food. For example, adding a preservative containing Boc-Laspartic Acid 1-benzyl Ester to fresh meat packaging can reduce the number of bacteria on the surface of fresh meat, delay its spoilage, and ensure its quality and safety.
Application examples in functional foods
Boc-Laspartic Acid 1-benzyl Ester is rich in amino acids, which are essential nutrients for the human body. Amino acids play an important role in maintaining normal physiological functions, promoting growth and development, and repairing tissues. In some foods for special populations, such as infant formula and athlete nutrition supplements, they can be added as nutritional fortifiers. For example, adding an appropriate amount of Boc-Laspartic Acid 1-benzyl Ester to infant formula can supplement amino acids and meet the nutritional needs of infants and young children for rapid growth and development.
This reaction is carried out under mild conditions and has the advantages of mild reaction conditions, simple operation, and high yield.
Detailed synthesis steps
Boc L-aspartic acid (4 g, approximately 30 mmol);Benzyl alcohol(appropriate amount, excess to increase reaction yield);Catalysts (such as sulfuric acid, p-toluenesulfonic acid, etc., in small amounts)
(1) In a dry 500 mL round bottomed flask, add Boc-L-aspartic acid and an appropriate amount of anhydrous ethanol as a solvent, stirring until completely dissolved.(2) Subsequently, benzyl alcohol and catalyst were sequentially added to the flask and thoroughly mixed.
Heat the reaction mixture to a certain temperature (such as reflux temperature) and stir the reaction at this temperature for several hours (such as 4-6 hours).During the reaction process, the reaction progress can be monitored by TLC (thin layer chromatography).
After the reaction is complete, cool the reaction mixture to room temperature and dilute with an appropriate amount of water.Use a rotary evaporator to remove most of the solvent and obtain a concentrated solution.
Transfer the concentrated solution to a separating funnel, add an appropriate amount of saturated sodium bicarbonate solution to neutralize the remaining acid, and extract with ethyl acetate.Merge the organic phases, dry with anhydrous sodium sulfate, and use a rotary evaporator again to remove the solvent.
The obtained product is vacuum dried to obtain white to almost white Boc-L-aspartate 1-benzyl ester powder.
FAQ
What is this drug?
It is a highly important protected amino acid derivative, commonly used as a key building block in peptide synthesis and organic pharmaceutical chemistry. Its molecular structure is modified with a Boc protecting group on the amino group and a benzyl ester group at the 1-position carboxyl site, which enables selective reaction at different functional sites during synthetic routes. This compound features stable chemical properties, good stereochemical purity, and convenient deprotection conditions, making it widely applied in the preparation of polypeptide drugs, chiral intermediates, and complex bioactive molecule synthesis.
What is its main application?
It is mainly used for solid-phase peptide synthesis and chiral intermediate preparation.
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