(S)-2-Amino-3-Phenylpropionic acid
L-Phenylalanine
CAS: 63-91-2;3617-44-5
Molecular Formula: C9H11NO2
(S)-2-Amino-3-Phenylpropionic acid - Names and Identifiers
| Name | L-Phenylalanine |
| Synonyms | PHE H-Phe-OH H-L-PHE-OH Phenylalanine L-Phenylalanie L-Phenylalanin L-Phenylalanine Phenyalanine, L- Phenylalanine, L- L-Alanine, phenyl- L(-)Phenylalaniline L-Antibiotic FN 1636 L-beta-Phenylalanine (S)-(-)-Phenylalanine l-beta-phenyl-alpha-alanin L-AminobenzenepropanoicAcid L-α-Amino-β-phenyl-propionsαure (S)-2-Amino-3-Phenylpropionic acid (S)-(-)-PHENYLALANINE FOR SYNTHESIS (S)-2-Amino-3-phenylpropionic acid~H-Phe-OH |
| CAS | 63-91-2 3617-44-5 |
| EINECS | 200-568-1 |
| InChI | InChI:1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12) |
| InChIKey | COLNVLDHVKWLRT-QMMMGPOBSA-N |
(S)-2-Amino-3-Phenylpropionic acid - Physico-chemical Properties
| Molecular Formula | C9H11NO2 |
| Molar Mass | 165.19 |
| Density | 1.29 |
| Melting Point | 270-275°C (dec.)(lit.) |
| Boling Point | 293.03°C (rough estimate) |
| Specific Rotation(α) | -34.1 º (c=2, water, dry basis) |
| Flash Point | 153.1°C |
| JECFA Number | 1428 |
| Water Solubility | 1-5 g/100 mL at 25 ºC |
| Solubility | Solubility in water (g/L):27g/L (20°C); Very slightly soluble in ethanol and methanol, hardly soluble in ether |
| Vapor Presure | <1 Pa (25 °C) |
| Appearance | White crystalline powder |
| Color | White to off-white |
| Merck | 14,7271 |
| BRN | 1910408 |
| pKa | 2.2(at 25℃) |
| PH | 5.0-7.0 (25℃, 0.1M in H2O) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Sensitive to light |
| Refractive Index | -34 ° (C=2, H2O) |
| MDL | MFCD00064227 |
| Physical and Chemical Properties | Solubility: H2O: 0.1 M at 20 ℃, clear, colorless WGK Germany:3 RTECS:AY7535000 |
(S)-2-Amino-3-Phenylpropionic acid - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R34 - Causes burns |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | AY7535000 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29224995 |
(S)-2-Amino-3-Phenylpropionic acid - Nature
Open Data Verified Data
White monoflaky, lobular or needle-like crystals. 283 degrees C decomposition. Very slightly soluble in ethanol, methanol.
Last Update：2024-01-02 23:10:35
(S)-2-Amino-3-Phenylpropionic acid - Preparation Method
Open Data Verified Data
after the defatted soybean was hydrolyzed with hydrochloric acid, acidic amino acids were removed, and phenylalanine and tyrosine were adsorbed with activated carbon or decolorizing resin. The phenylalanine may be dissolved and separated with a solvent.
Last Update：2022-01-01 09:26:27
(S)-2-Amino-3-Phenylpropionic acid - Standard
Authoritative Data Verified Data
This product is L-2-amino -3-phenyl propionic acid. Calculated as dried product, the content of C9H1N02 shall not be less than 98.5%.
Last Update：2024-01-02 23:10:35
(S)-2-Amino-3-Phenylpropionic acid - Trait
Authoritative Data Verified Data
- This product is white crystal or crystalline powder; Odorless.
- This product is soluble in hot water, slightly soluble in water, insoluble in ethanol; Soluble in dilute acid or sodium hydroxide solution.
specific rotation
take this product, precision weighing, add water to dissolve and quantitatively dilute to make a solution containing about 20mg per lml, and determine according to law (General 0621), the specific rotation was -33.0 ° to -35.0 °.
Last Update：2022-01-01 13:33:35
(S)-2-Amino-3-Phenylpropionic acid - Use
Open Data Verified Data
for biochemical studies, medium preparation.
Last Update：2022-01-01 09:26:27
(S)-2-Amino-3-Phenylpropionic acid - Differential diagnosis
Authoritative Data Verified Data
- appropriate amounts of the product and the phenylalanine reference product were dissolved and diluted with glacial acetic acid solution (50-100) to prepare a solution containing about 10 mg per 1 ml as the test solution and the reference solution. According to the chromatographic condition test under other amino acids, the position and color of the main spot of the test solution should be the same as that of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 983).
Last Update：2022-01-01 13:33:35
(S)-2-Amino-3-Phenylpropionic acid - Safety
Open Data Verified Data
- harmful by inhalation, ingestion and exposure. Such as the wrong to take this product, the wrong to take the consciousness does not occur spasm, can make the drink 1~2 glass of water to dilute, and then immediately sent to the hospital. Protective gear should be worn.
- in paper barrel, 25kg/barrel. Stay away from strong oxidants.
Last Update：2022-01-01 10:54:49
(S)-2-Amino-3-Phenylpropionic acid - Exam
Authoritative Data Verified Data
acidity
take 0.20g of this product, add 20ml of water to dissolve, and then measure it according to law (General rule 0631). The pH value should be 5.4~6.0.
transmittance of solution
take 0.50g of this product and add 25ml of water to dissolve it. According to ultraviolet-visible spectrophotometry (General rule 0401), determine the transmittance at 430nm wavelength, which shall not be less than 98.0%.
chloride
take 0.30g of this product and check it according to law (General rule 0801). Compared with the control solution made of 6.0 ml of standard sodium chloride solution, it should not be more concentrated (0.02%).
sulfate
take 0.70g of this product and check it according to law (General rule 0802). Compared with the control solution made of 0.02% of standard potassium sulfate solution, it should not be more concentrated ().
ammonium salt
take 0.10g of this product and check it according to law (General rule 0808). Compared with the control solution made of 2.0 ml of standard ammonium chloride solution, it shall not be deeper (0.02%).
other amino acids
take an appropriate amount of this product, add glacial acetic acid solution (50-100) to dissolve and dilute to make a solution containing about 10 mg per lml as a test solution; Take lml for precision measurement, add appropriate amount of phenylalanine reference substance and tyrosine reference substance to the same measuring flask, and add appropriate amount of glacial acetic acid solution (50-100) to dissolve, dilute with water to make about 10 mg phenylalanine and tyrosine per 1 ml. A solution of 1 mg, as a system-suitable solution. According to the thin layer chromatography (General 0502) test, draw 5ul of each of the above three solutions, respectively, on the same silica gel G thin layer plate, with n-butanol-glacial acetic acid-water (6:2:2) to develop, spread, dry, spray with ninhydrin in acetone solution (1-50), heat at 90°C until spots appear, and immediately inspect. The control solution should show a clear spot, and the system applicable solution should show two completely separated spots. If the test solution shows impurity spots, the color should not be deeper (0.5%) than the main spot of the control solution.
loss on drying
take this product, dry at 105°C for 3 hours, loss of weight shall not exceed 0.2% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Iron Salt
take l.Og of this product and check it according to law (General rule 0807). Compared with the control solution made of 0.001% of standard iron solution, it shall not be deeper ().
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
arsenic salt
take 2.0g of this product, add 23ml of water to dissolve, add 5ml of hydrochloric acid, check according to law (General rule 0822 first law), should comply with the provisions (0.0001%).
bacterial endotoxin
take this product, add human endotoxin test water, heat it in a warm water bath to dissolve it, check it according to law (General rule 1143), and the amount of endotoxin in each lg phenylalanine should be less than 25EU. (For injection)
Last Update：2022-01-01 13:33:36
(S)-2-Amino-3-Phenylpropionic acid - Content determination
Authoritative Data Verified Data
take this product about 0.13g, precision weighing, add anhydrous formic acid 3ml dissolved, add glacial acetic acid 50ml, according to the potential titration method (General rule 0701), with high gas acid titration solution (O. 1 mol/L) titration, and the results of the titration were corrected with a blank test. Each 1 ml of hydrochloric acid titration solution (0.1 mol/L) corresponds to 16.52mg of C9H1N02.
Last Update：2022-01-01 13:33:37
(S)-2-Amino-3-Phenylpropionic acid - Category
Authoritative Data Verified Data
amino acid drugs.
Last Update：2022-01-01 13:33:37
(S)-2-Amino-3-Phenylpropionic acid - Storage
Authoritative Data Verified Data
sealed storage.
Last Update：2022-01-01 13:33:37
(S)-2-Amino-3-Phenylpropionic acid - Reference Information
| FEMA | 3585 | L-PHENYLALANINE |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| properties | L-phenylalanine (PHE) is white flake crystal or crystalline powder, with slight special odor and bitter taste. About 283 ° C melting and decomposition, slightly soluble in water, insoluble in ethanol. |
| Application | L-Phenylalanine is an essential amino acid that cannot be synthesized by the human body. There are almost no limiting amino acids in the proteins of most food products. Can be added to baked food, in addition to strengthen phenylalanine, amino-carbonyl reaction with sugar, can improve the flavor of food. The food industry is mainly used as a synthetic raw material of food sweetener aspartame; It can also be used as a nutritional supplement. The refined Pharmacopoeia grade L-phenylalanine was used for the preparation of compound amino acid infusion. |
| content analysis | accurately weigh about 300mg of sample, dissolve in 3ml of formic acid and 50ml of glacial acetic acid, add 2 drops of crystal violet test solution (TS-74), with 0.1 mol/L perchloric acid titration to blue green endpoint. Perchloric acid corresponds to 16.52mg of L-phenylalanine (C9H11NO2) per mL of 0.1mol/L. |
| toxicity | LD505287mg/kg (rat, intraperitoneal injection). Safe for use in food (FDA,§ 172.320,2000). |
| usage limit | accounts for 5.8% of the total protein in food (FDA,§ 172.320,2000). F 'ema (mg/kg): baked goods 110; Frozen dairy products 60.0; Meat products 10.0; Soft candy 268; Gelatin, pudding 60.0; Dairy products 66.0; Condiment 10.0; Candy and frosting 268; sweet sauce 220. |
| Use | nutritional supplement. One of the essential amino acids. There are almost no limiting amino acids in the proteins of most food products. Can be added to baked food, in addition to strengthen the phenylalanine, and sugar from the amino carbonyl reaction, can improve the flavor of food. It can also be used to prepare amino acid infusion and comprehensive amino acid preparation. According to China GB 2760-86 regulations can be used as spices. used in biochemical research, preparation of culture medium, and used as amino acid nutrition medicine. amino acid drugs. For amino acid infusion, comprehensive amino acid preparation and nutrition enhancer. L-Phenylalanine is one of the essential amino acids. It is used as a component of Nutrition Fortifier, amino acid infusion and compound amino acid preparation. The product is a variety of anticancer drugs and dipeptide sweet raw materials. The main application is for functional food additives amino acid raw material medicine biochemical research. Medium was prepared. Nutrition research. |
| production method | The synthetic method for producing phenylalanine has a low yield and is usually extracted from natural products. After hydrolyzing defatted soybean with hydrochloric acid, acidic amino acids are removed, and phenylalanine and tyrosine are adsorbed with activated carbon or decolorizing resin. Then, phenylalanine is eluted and separated with a solvent. It is also possible to use a method in which phenylalanine in The hydrolysate is first converted into 2, 5-dibromobenzenesulfonate, and then the amino acids such as leucine and arginine are separated from each other by using the difference in solubility. There are many preparation methods of L-phenylalanine, such as protein hydrolysis extraction, direct fermentation, chemical synthesis and so on. The chemical synthesis methods include benzaldehyde method and phenylacetaldehyde method. Acetamidocinnamic acid was produced by the reaction of benzaldehyde and acetylglycine, and then it was reduced by catalytic hydrogenation to obtain acetyl-DL-phenylalanine (Ac-DL-phe), which was finally hydrolyzed by aminoacylase to form L-phenylalanine. Utilizing the specificity of aminoacylase, only Ac-L-phe of the amide bonds were hydrolyzed to yield L-phe, while Ac-D-phe of The amides could not be hydrolyzed. The separation was then carried out on the basis of the difference in solubility in water of L-phe and Ac-D-phe. And Ac-D-phe of the isolated can be racemized to Ac-DL-phe. The hydrolysis and separation were repeated again. By analogy, all Ac-DL-phe can be converted to L-phe. Preparation of immobilized aminoacylase after DEAE-sephadexa-50 was fully soaked in deionized water, it was then fully stirred with 10 times the amount of 0.5mol/L HCl and 0.5mol/L NaOH solution for 30min. Then, it was washed with deionized water until neutral, and finally treated with 0.1mol/L and 0.01mol/L of phosphate buffer solution of pH = 7.0 for 1-2H respectively, and dried by filtration. After culturing for 40-50H, the rice koji was expanded and extracted twice with 6 times the amount of branch ion water. The extract was adjusted to pH 6.7-7.0 with 2mol/L NaOH solution. Then, the mixture was mixed with 100L enzyme solution and 1kg wet DEAE-sephadex A- 50, and the mixture was stirred and adsorbed at 0-4 ℃ for 4-5H, then DEAE-sephadexA-50 was filtered and deionized water 0.1mol/L NaAc solution was used respectively, 0.01mol/L pH = 7.0 phosphate buffer was washed 3-4 times. Filtered to get immobilized aminoacylase, Add 1% toluene into the cold storage. Enzyme hydrolysis in 1000L hydrolysis tank, add 700L 0.1mol/L Ac-DL-phe sodium salt solution, then gradually add 6mol/L HCl to adjust the pH of the solution to 6.7-7.0, after 15-20kg of immobilized aminoacylase is added and the reaction is carried out at 50 ℃ for about 4H, the filtrate is filtered to obtain enzyme hydrolysate (L-phe and Ac-D-phe mixed liquor). Separation the enzyme hydrolysis solution was adjusted to pH 4.8-5.1 with 6mol/L HCl, concentrated to about 35L under reduced pressure, and left to crystallize at 0 °c overnight, and filtered to take crystals, wash with 10L cold ethanol and dry at 80 ℃ for 3-4H to obtain L-phe crude product. Combine filtrate and washing solution, and concentrate to about 20L under reduced pressure to obtain Ac-D-phe solution, the enzymatic hydrolysis and separation were repeated after the racemization. Ac-D-phe racemization 60L of the first solution was added to a Ac-D-phe L reaction tank, 18.5L of acetic anhydride was added, stirred at 25-45 °c for 30min, and cooled for 6H. Then adjust the pH value to 1.5-2.0 with concentrated HCl, crystallize at 5 ℃ overnight, filter the crystals, wash with water, filter dry at 40 ℃ and dry under vacuum, Ac-DL-phe. Refined in 100L reaction tank, add 5kg L-phe crude product, add 50L deionized water, heated to 100 ℃, stirred to dissolve, and then add 0.25 of medicinal activated carbon, after stirring and decoloring for half an hour, filter while hot, transfer the filtrate into a 200L crystallization tank, cool to 40 °c, add 50L of 95% ethanol at 40 °c, the pH was adjusted to 5.48 with 6mol/L HCl and crystallized overnight at 0 °c. The crystals were taken by filtration, washed with 95% ethanol, dried by suction, and dried at 80 °c for 3-4H to obtain L-phe finished product. The mother liquor was recovered. The phenylacetaldehyde method was applied to the Bucherer reaction to produce benzylhydantoin, which was then hydrolyzed to DL-phenylalanine (DL-phe). After DL-phe was reacted with acetic anhydride to form Ac-DL-phe, it was resolved as described above to obtain L-phe. with L-leucine as raw material, with 2, 5-dibromobenzenesulfonic acid reaction, 0 deg C crystallization to obtain crude product, and then ethylene glycol, methyl ether and water hot solution recrystallization refined. defatted soybeans are hydrolyzed with hydrochloric acid to remove acidic amino acids. After adsorption of phenylalanine, tyrosine and pigments with activated carbon or decolorizing resin, phenylalanine is dissolved and isolated. When separating from the hydrolysate, it is also possible to separate 2, 5-dibromobenzenesulfonate, which is hardly soluble in water, from leucine, arginine and the like by taking advantage of the difference in solubility. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:04:16
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