291°C (dec)
D-Alanine
CAS: 338-69-2
Molecular Formula: C3H7NO2
291°C (dec) - Names and Identifiers
| Name | D-Alanine |
| Synonyms | D-ALA D-ALANINE D-Alanine H-D-Ala-OH 291°C (dec) D-ALPHA-ALANINE D-2-Aminopropionic acid D-2-AMINOPROPIONIC ACID D-2-AMINOPROPANOIC ACID (R)-2-Aminopropionic acid |
| CAS | 338-69-2 |
| EINECS | 206-418-1 |
| InChI | InChI=1/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1 |
291°C (dec) - Physico-chemical Properties
| Molecular Formula | C3H7NO2 |
| Molar Mass | 89.09 |
| Density | 1.4310 (estimate) |
| Melting Point | 291°C (dec.)(lit.) |
| Boling Point | 212.9±23.0 °C(Predicted) |
| Specific Rotation(α) | -14.5 º (c=10, 6N HCl) |
| Water Solubility | 155 g/L (20 ºC) |
| Solubility | Soluble in water, slightly soluble in ethanol, insoluble in acetone and ether. |
| Appearance | Colorless crystal |
| Color | White to off-white |
| Merck | 14,204 |
| BRN | 1720249 |
| pKa | 2.31±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | -14 ° (C=2, 6mol/L H |
| MDL | MFCD00008077 |
| Physical and Chemical Properties | Properties D-alanine and L-alanine both have sugar taste, but different in taste specific optical rotation -14.5 ° (c = 10, 6N HCl) |
| Use | Raw materials for the synthesis of new sweeteners and some chiral drug intermediates |
291°C (dec) - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| TSCA | Yes |
| HS Code | 29224995 |
| Hazard Class | IRRITANT |
291°C (dec) - Reference
| Reference Show more | 1. Zhang Hai-Dan, Ye-fang-Mao Quan Gui-Lu-Heping, Liu Xue-Wei-Feng-Hui. Effects of alanine and trimethylamine on fermentation of lincomycin and transcription level of some related genes [J]. Jiangsu Journal of Agricultural Sciences 2014 30(05):1003-1009. 2. Talk about dream Xia, Chen Jiali, Zou Lisi, etc. Effects of different storage conditions on quality of Ophiopogon japonicus [J]. Chinese herbal medicine, 2018, 26 (11). 3. Chen, Yu-steel, Pu-po, et al. Comparative analysis of the contents of 21 amino acids in the disc of antler and its five extraction parts [J]. Journal of Pharmaceutical Analysis, 2017(10):1851-1857. 4. Cui Ruoyu, Li Meina, Fang Ting, etc. Study on fast Chiral separation of alanine by paper chromatography [J]. Chemical Education, 2018, 039(004):22-24. 5. Tang He Na, Yang Lei, Ouyang Zhi Yuan, etc. Preliminary Study on mineralization mechanism of seawater pearl based on biomimetic in vitro [J]. Chinese Journal of Electron Microscopy, 2017, 036(006):589-597. 6. Zhang Xifeng, Wang Xinxin, Zhang Qingting, Luo Guanghong. Separation of polysaccharide from oil peony seed meal by temperature-sensitive aqueous two-phase system with low eutectic solvent [J]. China Oils and fats, 2020,45(12):93-99. 7. Li, Suhong, et al. "Mechanisms of high concentration valine-mediated inhibition of peach tree shoot growth." Frontiers in Plant Science 11 (2020).https://dx.doi.org/10.3389/fpls.2020.603067 8. [IF=7.79] Ye Lu et al."Enhancing hydrogel-based long-lasting chemiluminescence by a platinum-metal organic framework and its application in array detection of pesticides and D-amino acids."Nanoscale. 2020 Feb;12(8):4959-4967 9. [IF=5.833] Lu Ye et al."Enzymatic determination of D-alanine using a cationic poly(fluorenylenephenylene) as the fluorescent probe and MnO2 nanosheets as quenchers."Microchim Acta. 2019 Jul;186(7):1-8 10. [IF=4.556] Dandan Zhao et al."Physico-chemical properties and free amino acids profiles of six wolfberry cultivars in Zhongning."J Food Compos Anal. 2020 May;88:103460 11. [IF=4.379] Feng Lin et al."Chemical profile changes during pile fermentation of Qingzhuan tea affect inhibition of α-amylase and lipase."Sci Rep-Uk. 2020 Feb;10(1):1-10 12. [IF=4.35] Xiaomei Dai et al."1-Methylcyclopropene Preserves the Quality of Chive (Allium schoenoprasum L.) by Enhancing Its Antioxidant Capacities and Organosulfur Profile during Storage."Foods. 2021 Aug;10(8):1792 13. [IF=4.242] Hang Yang et al."Dietary leucine requirement of juvenile largemouth bass (Micropterus salmoides) based on growth, nutrient utilization and growth-related gene analyses."Aquaculture. 2022 Jun;555:738207 14. [IF=3.463] Xiaomei Dai et al."S-alk(en)ylcysteine sulfoxides biosynthesis and free amino acids profile in different parts of postharvest chive (Allium schoenoprasum L.)."SCIENTIA HORTICULTURAE. 2022 Sep;303:111191 15. [IF=7.514] Xue Xia et al."Structural Diversity and Concentration Dependence of Pyrazine Formation: Exogenous Amino Substrates and Reaction Parameters during Thermal Processing of L-alanyl-L-glutamine Amadori Compound."FOOD CHEMISTRY. 2022 May;:133144 |
291°C (dec) - Standard
Authoritative Data Verified Data
This product is L-2-aminopropionic acid. Calculated as dried product, the content of C3H7N02 shall not be less than 98.5%.
Last Update：2024-01-02 23:10:35
291°C (dec) - Trait
Authoritative Data Verified Data
- This product is white or off-white crystal or crystalline powder; There is aroma.
- This product is soluble in water, insoluble in ethanol, acetone or ether; Soluble in lmol/L hydrochloric acid solution.
specific rotation
take this product, precision weighing, plus lmol / L hydrochloric acid solution dissolved and quantitatively diluted to make a solution containing about 50mg per lml, determined according to law (General 0621), the specific rotation was 14.0 ° to 15.0..
Last Update：2022-01-01 11:35:07
291°C (dec) - Differential diagnosis
Authoritative Data Verified Data
- appropriate amounts of this product and the alanine reference product were dissolved and diluted with water 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 915).
Last Update：2022-01-01 11:35:07
291°C (dec) - Exam
Authoritative Data Verified Data
acidity
take l.Og of this product, add water to dissolve 20ml, and then determine it according to law (General rule 0631). The pH value should be 5.5~7.0.
transmittance of solution
take l.Og of this product, add water 20ml to dissolve, according to ultraviolet-visible spectrophotometry (General rule 0401), measure the transmittance at 430nm wavelength, not 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 6.0ml of standard sodium chloride solution, it should not be more concentrated (0.02%).
sulfate
take this product L. 0g, check according to law (General rule 0802), and the standard potassium sulfate solution made of 0.02% ml of the control solution, not 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 0.02% of standard ammonium chloride solution, it shall not be deeper ().
other amino acids
take an appropriate amount of this product, add water to dissolve and dilute to make a solution containing about 25mg per lml as a test solution; Take lml for precision measurement and put it in a 200ml measuring flask, dilute to scale with water, shake well, as a control solution; Take the appropriate amount of alanine control and glycine control, and place in the same measuring flask, A solution containing 25mg of alanine and 0.125mg of glycine per 1 ml, respectively, was prepared by dissolving and diluting with water as a system-suitable solution. According to the thin layer chromatography (General 0502) test, absorb the above three solutions each 2 u1, respectively, on the same silica gel G thin layer plate, with n-butanol-water-glacial acetic acid (3:1:1) for the development of the agent, expand, dry, the same method and then expand once, dry. A solution of 0.2% ninhydrin in n-butanol in glacial acetic acid [n-butanol -2mol/L glacial acetic acid solution (95:5)] was sprayed and heated at 105°C until spots appeared and examined immediately. The control solution should show a clear spot, and the system applicable solution should show two completely separated spots. The test solution should not exceed 1 impurity spot, and its color should not be deeper (0.5%) compared with 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
not more than 0.1% (General rule 0841).
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
take 2.0g of this product, add 23ml of water to dissolve, add 2ml of acetate buffer (pH 3.5), and check according to law (General rule 0821 first law), containing heavy metals shall not exceed 10 parts per million.
arsenic salt
Take 2.OG 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, check according to law (General 1143), the amount of endotoxin in each lg alanine should be less than 20EU. (For injection)
Last Update：2022-01-01 11:35:08
291°C (dec) - Content determination
Authoritative Data Verified Data
take this product about 80mg, precision weighing, add anhydrous formic acid 2ml dissolved, add glacial acetic acid 50ml, according to the potential titration method (General rule 0701), with perchloric acid titration solution (O. 1 mol /L) titration, and the results of the titration were corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 8.909mg of C3H7N02.
Last Update：2022-01-01 11:35:09
291°C (dec) - Category
Authoritative Data Verified Data
amino acid drugs.
Last Update：2022-01-01 11:35:09
291°C (dec) - Storage
Authoritative Data Verified Data
sealed storage.
Last Update：2022-01-01 11:35:09
291°C (dec) - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | The chemical name of alanine (alanine;Ala) is 2-aminopropionic acid, which is an aliphatic non-polar α-amino acid. Alanine is a non-essential amino acid and a sugar-generating amino acid of the human body. It is mainly used in the synthesis of pantothenic acid and calcium pantothenate, carnosine, sodium pamidronate, balsalazide, etc., and is widely used in medicine, feed, food and other fields. It is also used for electroplating corrosion inhibitors and biochemical reagents. |
| Main features | 1. Structural alanine is the only spontaneously generated amino acid in biochemistry, and its amino group is located in the β position of carboxylate. According to the naming rules of IUPC, it should be called 3-amino-alanine. Unlike its common analog, L-α-alanine, β-alanine has no sign center. 2. In organisms, β-alanine does not participate in the synthesis of proteins or enzymes. Usually it is produced by the degradation of dihydrouracil and carnosine. Beta-alanine is also an important component of the spontaneously generated peptide carnosine and vitamin B5. Under normal conditions, beta-alanine is eventually metabolized to acetic acid. 3. Physiological effect β-alanine is one of the rare precursors of carnosine. It has been confirmed that supplementation of β-alanine can help increase the content of carnosine in muscle tissue, thereby eliminating (athlete) fatigue and improving muscle activity. 4. Studies have found that if the intake of β-alanine exceeds 10mg per kilogram of body weight, the body will induce paresthesia. The specific symptoms are mild and depend on the individual and the dose. However, the study also found that if β-alanine is ingested with chicken soup extract containing histamine acid, the body will not induce paresthesia. |
| Effect | 1. Alanine transport: The transmembrane transport of amino acids is essential for cell metabolism and nutrient transport in the body. At present, it is known that the absorption of amino acids is completed by membrane proteins called carriers on the cell membrane. Through these carriers, the amino acid substrate can be transported from one side of the cell membrane to the other, thereby performing its extensive and complex physiological functions. 2. Alanine and energy metabolism: Under stress conditions, food choices generally tend to be sugary and fatty foods, because hungry people tend to consume more energy and fat under stress. The energy released by glycolysis is the main energy supply mode of the small intestine, accounting for the 95% of energy generated by glucose metabolism, while alanine does not inhibit the glycolysis of small intestinal epithelial cells. 3. Alanine-glucose cycle: Alanine is an important sugar-producing amino acid for monogastric animals and ruminants, which can act as a carrier for glucose-derived carbon skeleton for glucose synthesis. Alanine can participate in the glucose-alanine cycle between tissues and liver. 4. Alanine and other amino acid metabolism: Alanine is very important for cell growth and physiological metabolism. It is one of the very important amino acids that make up proteins and can synthesize valine and biotin. In addition, the glucose and alanine cycle illustrates the relationship between branched-chain amino acids (BCAA) and glucose metabolism. When the branched-chain amino acids are oxidized, alanine is subsequently formed and released into the blood, entering the liver to support gluconeogenesis. 5. Alanine and ammonia excretion: Some amino acids, such as arginine, glutamic acid, histidine and proline can produce glutamine. The alanine-pyruvate cycle is of great significance to the improvement of the body's nitrogen utilization rate, the resulting environmental improvement, and the reduction of nitrogen emissions. 6. Effect of alanine on microorganisms: Alanine is the main component of the peptidoglycan layer of the bacterial cell wall. 7. Alanine and stress in piglets: Exogenous alanine may inhibit the metabolic response of lactate production of alanine, which does not seem to be conducive to improving the stress state of piglets. |
| use | alanine is mainly used for synthesizing pantothenic acid, calcium pantothenate, carnosine, sodium pamidronate, balsalazide, etc. it is widely used in medicine, feed, food and other fields. It is also used for electroplating corrosion inhibitors and biochemical reagents. Used for biochemical research. Raw materials for the synthesis of new sweeteners and certain chiral drug intermediates D-alanine is an important organic chiral source, mainly used in chiral drugs |
| application | aminopropionic acid is a white or light yellow crystalline powder. the main users synthesize pantothenic acid, calcium pantothenate, carnosine, sodium pamidronate, balsalazide, etc. and are widely used in medicine, feed, food and other fields. |
| production method | using N-acetyl-DL-alanine as raw material, after acylase resolution to remove L-alanine, hydrochloric acid hydrolysis, recrystallization and refining. |
Last Update：2024-04-09 20:48:19
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View History
291°C (dec)
POLYOXYPROPYLENE METHYL DIETHYL AMMONIUM CHLORIDE)
(5-((4-(叔-丁氧基羰基)哌嗪-1-基)磺酰)-2-甲基苯基)硼酸
二(2-溴乙基)氨基甲酸叔丁酯
HYDROCORTISONE PHOSPHATE TRIETHYLAMINE
甲萘酚硫酸钠
Z-Acp-leu-metyr-MA
2-(2-bromophenoxy)nicotinamide
5-(N-吗啉基甲基)-3-异恶唑甲酸盐酸盐
2-PROPANESULFINAMIDE, N-[(1R)-1-(2-CHLOROPHENYL)ETHYL]-2-METHYL-, [S(R)]-
POLYOXYPROPYLENE METHYL DIETHYL AMMONIUM CHLORIDE)
(5-((4-(叔-丁氧基羰基)哌嗪-1-基)磺酰)-2-甲基苯基)硼酸
二(2-溴乙基)氨基甲酸叔丁酯
HYDROCORTISONE PHOSPHATE TRIETHYLAMINE
甲萘酚硫酸钠
Z-Acp-leu-metyr-MA
2-(2-bromophenoxy)nicotinamide
5-(N-吗啉基甲基)-3-异恶唑甲酸盐酸盐
2-PROPANESULFINAMIDE, N-[(1R)-1-(2-CHLOROPHENYL)ETHYL]-2-METHYL-, [S(R)]-