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L-phenylalanine powder is an organic compound with the molecular formula of C9H11NO2. Colorless to white flake crystals or white crystalline powder. Slightly special smell and bitter taste. Stable in heat, light and air. It is mainly used for biochemical research, preparation of culture medium and nutrition research. Nutritional supplements. One of the essential amino acids. In most food proteins, there are almost no restricted amino acids. L-phenylalanine can be added to baked food. In addition to strengthening phenylalanine, L-phenylalanine can react with sugars to form amino carbonyl group, which can improve the flavor of food.
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Chemical Formula |
C9H11NO2 |
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Exact Mass |
177 |
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Molecular Weight |
177 |
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m/z |
165 (100.0%), 166 (9.7%) |
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Elemental Analysis |
C, 65.44; H, 6.71; N, 8.48; O, 19.37 |
L-phenylalanine powder (L-phenylalanine) is an essential amino acid, and its powder form has a wide range of applications in various fields such as food, medicine, chemical engineering, agriculture, and scientific research. The following is a detailed explanation of its purpose:
Food Industry: Core Raw Materials for Nutritional Fortification and Flavor Improvement
L-phenylalanine is one of the eight essential amino acids for the human body and is crucial for maintaining normal physiological functions. In the food industry, L-phenylalanine is often used as a nutritional fortifier, added to various foods to supplement the deficiency of amino acids in food, especially for infant formula foods, sports nutrition products, and special medical formula foods.
Infants and young children are in a critical period of growth and development, and their demand for essential amino acids is particularly urgent. The addition of L-phenylalanine helps to make infant formula foods closer to the amino acid composition of breast milk, supporting the development of their brain and nervous system.
After high-intensity training, athletes experience a significant increase in amino acid consumption in their bodies. L-phenylalanine, as a key ingredient in sports drinks, protein bars, and other products, can quickly supplement amino acids, promote muscle repair and energy recovery, and improve athletic performance.
Nutritional fortifiers: the core raw material for enhancing the nutritional value of food
The addition of L-phenylalanine not only directly increases the amino acid content of food, but also helps optimize the overall nutritional formula of food. By precisely controlling the amount of L-phenylalanine added, the nutritional value label of food can be enhanced to meet consumers' demand for healthy food. Clearly labeling the content of L-phenylalanine on food packaging helps consumers understand the nutritional characteristics of the product and choose foods that meet their own needs. Among similar products, adding L-phenylalanine to enhance nutritional value can create product differentiation and enhance market competitiveness.
L-phenylalanine can undergo amino carbonyl reaction (Maillard reaction) with sugars in food processing, generating compounds with special flavors, significantly improving the aroma and taste of food. In baked goods such as bread and cakes, L-phenylalanine reacts with reducing sugars to produce flavors such as caramel and nutty, enhancing the sensory quality of the product and attracting consumers. In dairy products such as yogurt and cheese, L-phenylalanine participates in the Maillard reaction, enhancing the flavor complexity of the product and meeting consumers' expectations for high-quality dairy products.
In seasonings such as oil and sauce, L-phenylalanine generates compounds with meat and grilled flavors through the Maillard reaction, enhancing the freshness and layering of seasonings and enriching cooking options. In the field of compound seasoning, ready to eat food and other fields, L-phenylalanine powder can be combined with other amino acids, essence and other flavor substances to develop a unique compound flavor to meet the taste preferences of different consumers. By optimizing the addition amount and reaction conditions of L-phenylalanine, the stability of food flavor can be improved, the shelf life of products can be extended, and flavor loss can be reduced.
Sweetener synthesis: key raw material for aspartame production
L-phenylalanine is the core raw material for synthesizing Aspartame. Aspartame, as a low calorie high-intensity sweetener, has a sweetness 200 times that of sucrose and is widely used in sugar free beverages, chewing gum, candies, and other foods. The synthesis of aspartame usually uses L-phenylalanine and L-aspartic acid as raw materials and is generated through chemical methods. The quality of L-phenylalanine directly affects the purity and sweetness of aspartame, which in turn affects the taste and quality of the final product.
Chemical industry: key raw materials for the synthesis of fragrances and dyes
L-phenylalanine is an important raw material for synthesizing various natural spice mimetics with floral and fruity characteristics. The benzene ring in its molecular structure endows the compound with aromaticity, while the amino and carboxyl groups can introduce functional groups through chemical reactions, thereby replicating the chemical skeleton of natural flavors. Through oxidation reaction, L-phenylalanine can be converted to phenylacetaldehyde. This compound has the aroma of hyacinth and is widely used in the formulation of floral essence. For example, phenylacetaldehyde is the core ingredient for preparing rose, lilac and other floral essence, with pure fragrance and lasting fragrance.
L-phenylalanine can generate phenylethanol through reduction reaction. Its sweet rose fragrance makes it a key component of perfume and cosmetic essence. Phenylethanol can not only be used directly as a fragrance, but also derive more fragrance variants through esterification reactions. Methyl cinnamate, ethyl cinnamate and other compounds, which are synthesized from L-phenylalanine, have strong fruit aroma and are commonly used in the preparation of fruit essence. These ester compounds play an important role in food essence such as beverages and candy.
Spice synthesis field
The molecular structure plasticity of L-phenylpropanolamine makes it an ideal platform for the design of novel spice molecules. By introducing different substituents or coupling with other spice molecules, new compounds with unique aroma characteristics can be synthesized. Nitrogen containing heterocyclic compounds such as pyridine and pyrazine can be synthesized through cyclization reaction using L-phenylalanine as raw material. These compounds have characteristic aroma such as nutty aroma and roasted aroma, and are widely used in baked food and tobacco essence.
Synthesis of macrocyclic fragrances: By utilizing the amino acid properties of L-phenylalanine, macrocyclic lactone fragrances can be synthesized through multi-step reactions. These compounds have musky aroma and are indispensable fixatives in high-end perfume and cosmetics.
Chiral spice synthesis: The chiral center of L-phenylalanine makes it an important raw material for synthesizing chiral spices. Through asymmetric synthesis technology, spice molecules with specific optical activity can be prepared to meet consumers' demand for natural aroma.
L-phenylalanine can endow flavor molecules with new functional properties through chemical modification, and broaden its application in essence formulations. Combining L-phenylalanine with polymer materials can prepare sustained-release spice microspheres. This kind of flavor can be released slowly in the essence system, which can extend the fragrance retention time and improve the use experience of the product. By introducing photoresponsive groups, photosensitive L-phenylalanine derivatives can be synthesized.
This kind of perfume can release fragrance under light conditions, and is suitable for innovative fields such as light essence and intelligent packaging. L-phenylalanine derivatives can be combined with functional groups such as antibacterial and antioxidant to prepare bioactive spice molecules. These types of spices not only provide pleasant aromas in cosmetics and personal care products, but also have skincare benefits.
L-phenylalanine powder, as a multifunctional amino acid supplement, demonstrates broad application prospects in the fields of neurological health, metabolic regulation, and disease treatment. From molecular mechanisms to clinical practice, it provides scientific intervention strategies for complex diseases such as depression, obesity, and phenylketonuria by participating in neurotransmitter synthesis, protein metabolism, and energy balance. Looking ahead, with advancements in personalized nutrition and novel delivery technologies, L-phenylalanine powder is poised to become a vital tool in precision medicine and health management, contributing significantly to human health and well-being.
There are many methods to prepare L-phenylalanine, including protein hydrolysis, direct fermentation, chemical synthesis, etc. Chemical synthesis methods include benzaldehyde method and phenylacetaldehyde method.
1. Benzaldehyde method:
Acetaminocinnamic acid is produced by the reaction of benzaldehyde and acetylglycine, and then acetyl DL phenylalanine (Ac DL phe) is obtained by catalytic hydrogenation reduction. Finally, it is hydrolyzed by aminoacylase to generate L-phenylalanine.
Separation Adjust the pH of the enzyme hydrolysate to 4.8-5.1 with 6mol/L HCl, reduce the pressure and concentrate it to about 35L, place it at 0 ℃ for crystallization overnight, filter it for crystallization, wash it with 10L cold ethanol, dry it at 80 ℃ for 3-4h to obtain L-phe crude product, combine the filtrate and washing solution, reduce the pressure and concentrate it to about 20L to obtain Ac-D-phe solution, and repeat the enzyme hydrolysis and separation after racemization.
Racemization of Ac-D-phe Add 60L of Ac-D-phe solution into 100L reaction tank, 18.5L of acetic anhydride, stir for 30min at 25-45 ℃, and cool for 6h. Then adjust the pH value to 1.5-2.0 with concentrated HCl, crystallize at 5 ℃ overnight, filter for crystallization, wash with water, filter dry at 40 ℃ and vacuum dry to obtain Ac DL phe.
Refine in a 100L reaction tank, add 5kg L-phe crude product, add 50L deionized water, heat to 100 ℃, stir to make it completely soluble, add 0.25kg of medicinal active carbon, stir and decolorize for half an hour, filter while hot, transfer the filtrate into a 200L crystallization tank, cool to 40 ℃, add 50L of 95% ethanol at 40 ℃, adjust the pH to 5.48 with 6mol/L HCl, crystallize at 0 ℃ overnight, filter and crystallize, wash with 95% ethanol, drain, and dry at 80 ℃ for 3-4 hours, Get l-phenylalanine finished product. Mother liquor is recycled.
2. Phenylacetaldehyde method:
It is suitable for Bucherer reaction to generate phenylmethyl hydantoin, and then alkaline hydrolysis to obtain DL phenylalanine (DL phe).
After DL phe is reacted with acetic anhydride to form Ac DL phe, L-phenylalanine powder can be obtained by the above method.
3. Protein hydrolysis extraction method:
The yield of phenylalanine prepared by synthesis is low, and it is usually extracted from natural products. After the degreased soybean is hydrolyzed with hydrochloric acid, the acidic amino acids are removed, and phenylalanine and tyrosine are adsorbed with activated carbon or decolorized resin. Then, phenylalanine is dissolved and separated with solvent. Alternatively, phenylalanine in the hydrolysate can be converted into 2,5-dibromobenzene sulfonate, and then separated from amino acids such as leucine and arginine by using the difference in solubility.
Frequently Asked Questions
What is the difference between D and L-phenylalanine?
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L-phenylalanine is an essential amino acid. It is the only form of phenylalanine found in proteins. D-phenylalanine is not an essential amino acid, and its role in the body is not currently understood. DL-phenylalanine is made in a lab.
Does L-phenylalanine give you energy?
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l-Phenylalanine (Phe), is a potent releaser of the satiety hormone, cholecystokinin (CCK) and previous studies, conducted primarily in men, show that ingestion of Phe reduces energy intake.
Does phenylalanine cause weight gain?
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The phenylalanine amino acid is an essential amino acid that is important for growth and development as well as the production of several neurotransmitters and hormones. Some studies suggest this amino acid could promote weight loss, reduce chronic pain and protect against depression.
Can phenylalanine cause hair loss?
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However, sporadic case reports indicate that low phenylalanine levels may be associated with eczematous rashes, hair loss, visual problems, prolonged diarrhea, and failure to thrive in infants.
Is phenylalanine bad for your kidneys?
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Phenylalanine, along with tyrosine and tryptophan, are precursors of major uremic toxins such as p-cresyl sulfate (PCS) and indoxyl sulfate (IS), which are known to contribute to the progression of chronic kidney disease (CKD).
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