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L-tyrosine powder, CAS 60-18-4, Molecular formula C9H11NO3, white to off white powder. Soluble in acid and alkali solutions, slightly soluble in water, insoluble in absolute ethanol, ether and acetone. It is an important nutritional essential amino acid and plays an important role in human and animal metabolism, growth and development.
It is widely used in food, feed, medicine, chemical industry and other industries. It is often used as a nutritional supplement for phenylketonuria patients, and as a raw material for the preparation of polypeptide hormones, antibiotics, L-dopa, melanin, p-hydroxycinnamic acid, p-hydroxystyrene and other pharmaceutical and chemical products. However, with the discovery of more high-value L-tyrosine derivatives such as danshensu, resveratrol and hydroxytyrosol in vivo, L-tyrosine is increasingly developing towards platform compounds.
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Chemical Formula |
C9H11NO3 |
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Exact Mass |
181 |
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Molecular Weight |
181 |
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m/z |
181 (100.0%), 182 (9.7%) |
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Elemental Analysis |
C, 59.66; H, 6.12; N, 7.73; O, 26.49 |
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L-tyrosine powder, as an aromatic non essential amino acid, is endowed with unique chemical properties and biological activity by its phenolic hydroxyl and amino groups in its molecular structure. Since its first separation from cheese in 1846, its application has expanded from basic nutritional supplements to diverse fields such as medicine, food, daily chemical products, agriculture, and scientific research, forming an interdisciplinary technical system.
Medical field: Core raw materials for neurotransmitter regulation and disease treatment
Neurotransmitter Precursors and Psychological Disease Intervention
It is a key precursor for the synthesis of dopamine, norepinephrine, and adrenaline. In the treatment of depression, supplementing L-tyrosine can increase dopamine levels in the brain and improve emotional and cognitive function in patients with mild to moderate depression. Clinical studies have shown that when combined with vitamin B6, C, and L-tryptophan, the absorption rate increases by 40%, and the relief effect on anxiety type depression is significant. In addition, as an adjuvant therapy for Parkinson's disease, L-tyrosine can supplement the loss of dopaminergic neurons in the substantia nigra and improve symptoms of bradykinesia.
Nutritional intervention for genetic metabolic diseases
Patients with phenylketonuria (PKU) suffer from L-tyrosine deficiency due to phenylalanine hydroxylase deficiency and require lifelong supplementation of L-tyrosine to maintain normal growth and development. The National Safety Standard for Infant Formula Food in China clearly stipulates that the L-tyrosine content.
Raw materials for drug synthesis
L-tyrosine is a core raw material for the preparation of peptide hormones (such as thyrotropin releasing hormone), antibiotics (such as polymyxin E), and L-dopa (a drug for treating Parkinson's disease). Its derivative N-acetyl-L-tyrosine has been used to develop new antidepressant drugs due to its stronger ability to penetrate the blood-brain barrier.
Food Industry: Drivers of Nutritional Fortification and Functional Innovation
Nutritional fortification of high protein foods
Adding L-tyrosine to dairy products, meat products, and protein bars can significantly increase the protein content and bioavailability of the products. For example, adding 0.5% L-tyrosine to whey protein powder increases the PDCAAS (protein digestibility corrected amino acid fraction) value from 1.0 to 1.2, which is closer to the human amino acid demand pattern.
Functional food development
Sports nutrition: By promoting adrenaline synthesis, it delays exercise fatigue. Supplementing with 1.5g L-tyrosine before endurance exercise can prolong athletes' exercise time by 12%.
Food processing aids
Maillard reaction with reducing sugar produces meat flavor substances, which are widely used in the preparation of meat flavor essence. It can also inhibit the formation of magnesium ammonium phosphate crystals in canned shrimp and crab, extending the product shelf life.
In the field of daily chemical products: active ingredients for whitening, anti-aging, and skin repair
Research and development of whitening cosmetics
Reduce melanin production by competitively inhibiting tyrosinase activity. The clinical test showed that the skin color brightness (L * value) of the subjects increased by 1.8 and the melanin index decreased by 15% after the whitening essence containing 2% L-tyrosine powder was used continuously for 8 weeks. When combined with niacinamide and tranexamic acid, the synergistic whitening effect is increased by three times.
Application of anti-aging skincare products
The phenolic hydroxyl structure of L-tyrosine endows it with strong antioxidant capacity, with a DPPH radical scavenging rate of 89%, higher than vitamin C (78%). Adding 1% L-tyrosine to the anti wrinkle face cream can significantly increase the collagen content in the skin by 22% and reduce the wrinkle depth by 18%.
Hair care products
By promoting the activity of melanocytes, early white hair can be improved. Adding 0.5% L-tyrosine to hair dye can reduce the irritation of hydrogen peroxide on the scalp and improve the durability of hair dye.
Agriculture and Feed: Key Nutrients for Animal Growth and Health
Improvement of livestock and poultry production performance
Adding 0.2% L-tyrosine to piglet diets can increase daily weight gain by 8% and feed conversion rate by 6%.
Its mechanism is related to promoting growth hormone secretion and intestinal development.
Enhanced stress resistance of aquatic animals
Adding 0.1% L-tyrosine to the feed of South American white shrimp can significantly improve its low oxygen tolerance and increase the survival rate of aquaculture by 12%.
Development of serum-free culture medium
L-tyrosine is an essential component of serum-free culture media such as CHO cells and HEK293 cells. In monoclonal antibody production, supplementing L-tyrosine can increase antibody production by 15% while reducing cell apoptosis rate.
Research on Protein Structure and Function
As a standard for determining peptide nitrogen content, it is used for colorimetric quantitative analysis in the Milon reaction. Its derivative fluorescently labeled tyrosine (FITC Tyr) has been widely used in protein interaction research.
With the development of synthetic biology and delivery technology, the application boundaries of L-tyrosine will continue to expand. For example, constructing a high-yield L-tyrosine microbial cell factory through gene editing technology can reduce production costs; Targeted modification of L-tyrosine nanoparticles will achieve tumor tissue specific accumulation and enhance chemotherapy efficacy.
The early production of L-tyrosine powder mainly depends on protein hydrolysis. However, protein hydrolysis has been eliminated due to its limited material sources, complex process and products, and long cycle. L-tyrosine is mainly produced by enzymatic method, microbial fermentation method, extraction method and chemical method.
Enzymatic method
Enzymatic method, also known as microbial transformation method, mainly uses tyrosine phenol lyase (TPL, EC 4.1.99.2) in microbial cells to convert phenol, pyruvic acid and ammonia or phenol, L-serine into L-tyrosine. TPL with higher enzyme activity and more research results mainly comes from the microorganism Erwinia herbicola, Citrobacter intermedius, Citrobacter freundii and Thermophilic bacteria. Lee and Hsiao of Genex Company were the first to use Klebsiella aerogenes serine hydroxymethyltransferase and Erwinia herbicola ATCC 21434 tyrosine phenol lyase to couple the reaction of synthesizing L-serine with glycine as the substrate and the reaction of synthesizing L-tyrosine with L-serine as the substrate in 1986.
Add 0.32% phenol, 0.25 M glycine, 0.5 mM 5-pyridoxal phosphate, 0.056 M in 500 mL reaction system β- Mercaptoethanol, 1.7 mM tetrahydrofolate. Under pH 7.0 and 37 ℃, the reaction was started with 37% formaldehyde. After 16 hours, 26.3 g/L L-tyrosine was produced, and the conversion rate of glycine reached 61.4%. However, the stability of this process is poor and glycine has a strong inhibitory effect on TPL activity.
Considering the poor enzyme activity and stability in the reaction process, the use of DNA shuffling technology to improve the stability of TPL has also attracted attention in recent years. Eugene et al. of KRIBB in South Korea obtained AS6 mutant with catalytic activity increased by three times and half inactivation temperature increased by 11.2 ℃ through random mutation screening of TPL in Symbiobacterium toebii and staggered DNA shuffling.
The sequencing results showed that there were T129I or T451A mutations in the catalytic active region, and three mutations including A13V, E83K and T407A were of great help to improve the thermal stability. And Kim et al. of this research group in E Coli BL21 (DE3) over expressed the TPL with improved catalytic activity and thermal stability, and prepared the crude catalytic extract. In the 2.5L flow addition reactor system, 2.2 M phenol, 2.4 M sodium pyruvate, 0.4 mM 5-pyridoxal phosphate and 4 M ammonium chloride were added in batches, and nitrogen was filled above the reaction tank to reduce the oxidation of substrate. 130 g/L L-tyrosine could be accumulated after reaction at 40 ℃ for 30 hours, and the highest conversion rate of phenol could reach 94%.
Extraction method
The extraction method was first invented by Bracannot in 1820. He extracted glycine and leucine from gelatin sheepskin and muscle hydrolysate. After that, Bopp et al. gradually hydrolyzed tyrosine and serine from protein. The oldest process of amino acid production, namely, white matter hydrolysis extraction. Protein can be hydrolyzed by enzyme, acid or ingenuity, and the final product is amino acid.
6 M hydrochloric acid is commonly used to hydrolyze at 110 ℃ for 12-24 hours. After the excess acid is removed, the mixture of various amino acids is extracted. Finally, the relative purity of amino acids was obtained by the method of solubility difference or ion exchange resin.
By the 1930s and 1940s, more than 20 kinds of amino acids could be obtained by using the extraction method. The most famous amino acid industry is monosodium glutamate.
Today, although most amino acids can be extracted from various resources, due to the high cost of resources, low yield, environmental pollution and other reasons, it is not suitable to continue large-scale production. The extraction method for the production of cardiac tyrosine is generally to use natural protein resources as raw materials, hydrolysis, concentration, crystallization, decolorization and other steps to separate and extract cardiac tyrosine. However, because the content of L-tyramine in the extracted product is low, the yield of the extraction method is actually low, so it is not suitable for large-scale production.
FAQ
What is the benefit of L-tyrosine?
L-Tyrosine is a non-essential amino acid supplement that boosts cognitive performance, alertness, and focus, particularly under high-stress conditions, cold exposure, or sleep deprivation. It works by increasing neurotransmitters like dopamine and norepinephrine, helping to improve memory and reaction time. It may also aid in regulating mood and supporting thyroid function.
Is L-tyrosine safe to take daily?
L-tyrosine is generally considered safe for daily, short-term use (up to 3 months) by most healthy adults, often used for stress and cognitive support. While high doses (up to 150 mg/kg) have been safe in studies, long-term safety data is lacking. Potential side effects include headaches, nausea, and fatigue.
Can I take L-tyrosine if I have hypothyroidism?
Does L-tyrosine affect sleep?
L-tyrosine generally acts as a stimulant and cognitive enhancer, making it unlikely to cause sleepiness and often promoting alertness instead. By increasing neurotransmitters like dopamine and norepinephrine, it improves mental performance under stress and during sleep deprivation, which can interfere with falling asleep if taken late.
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