DL-Serine
DL-Serine
CAS: 302-84-1
Molecular Formula: C3H7NO3
DL-Serine - Names and Identifiers
| Name | DL-Serine |
| Synonyms | DL-Serine DL-Ser-OH H-DL-Ser-OH DL-SERINE UNLABELED DL-SERINE extrapure CHR DL-SERINE TECHNICAL GRADE (2S)-2-ammonio-3-hydroxypropanoate rac-(R*)-2-Amino-3-hydroxypropionic acid |
| CAS | 302-84-1 |
| EINECS | 206-130-6 |
| InChI | InChI=1/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1 |
DL-Serine - Physico-chemical Properties
| Molecular Formula | C3H7NO3 |
| Molar Mass | 105.09 |
| Density | 1.53 |
| Melting Point | 240 °C (dec.) (lit.) |
| Boling Point | 197.09°C (rough estimate) |
| Flash Point | 192.6°C |
| Water Solubility | 50.23 g/L (25 ºC) |
| Solubility | H2O: soluble |
| Vapor Presure | 7.17E-08mmHg at 25°C |
| Appearance | Colorless crystal |
| Color | White |
| Odor | Odorless |
| Merck | 14,8460 |
| BRN | 1721402 |
| pKa | 2.19(at 25℃) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 1.4368 (estimate) |
| MDL | MFCD00064223 |
| Physical and Chemical Properties | Density 1.53 melting point 240°C (dec.) water-soluble 50.23g/L (25°C) |
| Use | Used as a Biochemical reagent |
DL-Serine - 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 |
| RTECS | VT8100000 |
| TSCA | Yes |
| HS Code | 29225000 |
DL-Serine - Reference
| Reference Show more | 1. Zhang Cong. Effects of endogenous sphingosine metabolites on rat retinal microvascular endothelial cells [J]. Beijing University of Chinese Medicine, 2020. 2. Xiaokui Huo, Xiangge Tian, Yannan Li, Lei Feng, Yongle I Cui, Chao Wang, Jingnan Cui, Peng Peng Sun, Kexin Liu, Xiaochi Ma, A highly selective rational fluorescent probe for real-time imaging of β-glucuronidase in living cells and zebra fish, Sensors and 3. [IF = 5.923] Cuihua Chen et al."Variations in Physiology and Multiple Bioactive Constituents under Salt Stress Provide Insight into the Quality Evaluation of Apocyni Veneti Folium."Int J Mol Sci. 2018 Oct;19(10):3042 4. [IF=4.759] Jingtang Li et al."Synthesis and application of ionic liquid functionalized β-cyclodextrin, mono-6-deoxy-6-(4-amino-1,2,4-triazolium)-β-cyclodextrin chloride, as chiral selector in capillary electrophoresis."J Chromatogr A. 2018 Jul;1559:178 |
DL-Serine - Introduction
Solubility in water (g/L)0 ℃ 22-04g/L;25 ℃ 50-23g/L;50 ℃ 103g/L;75 ℃ 192g/L;100 ℃ 322g/l. Insoluble in anhydrous ethanol and ether.
Last Update：2022-10-16 17:24:25
DL-Serine - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | serine is a non-essential amino acid. it plays a role in the metabolism of fat and fatty acids and muscle growth, because it helps to immunize the production of hemoglobulin and antibodies, and serine is also needed to maintain a healthy immune system. Serine plays a role in the production and processing of cell membranes, the synthesis of muscle tissue and the sheath surrounding nerve cells. |
| Non-essential amino acids for human body | DL-serine, also known as 2-amino-3-hydroxypropionic acid, β-hydroxyalanine, hydroxyaminopropionic acid, an aliphatic neutral amino acid containing hydroxyl, polar but not charged, is a non-essential amino acid for human body, and is rich in sericin and sericin, it can be formed from glycine to methyl, and can also be deaminated into pyruvate or hydroxypyruvate. It is also an important raw material for the synthesis of choline and cysteine in the body. It was first separated from the sulfuric acid hydrolysis solution of sericin in 1865. There are left-handed bodies and racemates. The left-handed body crystallized from water is hexagonal flake or prismatic white crystal or crystalline powder. No smell. Sweet. Relative molecular mass 105.09. Decomposition at 228 ℃. Sublimation at 150 ℃ under vacuum. Optical rotation -6.83 (10% aqueous solution). Insoluble in organic solvent, insoluble in absolute ethanol and ether, soluble in acid and alkali, soluble in water 25.4(10 ℃), 38(20 ℃), 48.5(30 ℃), 60.5(40 ℃), 72.0(50 ℃), 83.0(60 ℃) and formic acid. For biochemistry and nutrition research. It is also used as a raw material for the synthesis of cycloserine. Distributed in a variety of proteins, especially silk proteins. The content is centered in the amino acid composition of marine plankton. It exists in seawater, particulate matter and marine sediments in a free and combined state, and can be obtained by separating and refining protein hydrolysates. It can also be prepared by amination and demethylation of α-bromo-β-methoxypropionic acid. The racemate crystallized from water is a monoclinic white crystal. Relative density 1.537. Decomposition at 246 ℃. Sublimation at 150 ℃ in high vacuum. Soluble in water (g/l)22.04(0 ℃), 50.23(50 ℃), 192(75 ℃), 322 (100 ℃), insoluble in absolute ethanol, ether, benzene and acetic acid. It reacts with hydrogen peroxide and ferrous sulfate to form hydroxyacetaldehyde, reacts with ferric chloride solution to show red, reacts with hydrochloric acid to obtain hydrochloride, and reacts with alcohol to form serine ester in the presence of dehydrating agent. Main purposes: 1. In addition to being used as a raw material for protein synthesis and providing carbon frames in the synthesis of purine, thymine, methionine and choline, the active center composition of some enzymes and the operation of the glycolic acid pathway in plants require it to participate. 2. Because of its special wettability, it is used as a cosmetic additive for cream (moisturizer) to maintain the moisture of the stratum corneum and maintain the softness of the skin; food additive, used as a nutritional supplement; pharmaceutical raw materials and infusion. |
| preparation method | DL-serine can be prepared by the following methods: 1. extraction method. The protein containing more serine was hydrolyzed and then extracted and refined with ion exchange resin. 2. Using glycolaldehyde, hydrocyanic acid and ammonia as raw materials, it can be synthesized, and then hydrolyzed to obtain amino nitrile. 3. Fermentation. It can be prepared by fermentation with glucose as carbon source, glycine as precursor, Corynebacterium glycinophilus or Octococcus microalbicans. Or methanol as the carbon source, using Pseudomonas 3ab or Pseudomonas MS31, etc. after fermentation can be prepared. 4. Acrylonitrile is used as raw material, chlorinated to generate α,β-dichloropropiononitrile, reammoniated to generate α-chloro-β-aminopropiononitrile, and then aziridin-2-carboxylic acid is generated in alkali solution Sodium, DL-serine can be prepared by strong acidic cation exchange resin. 5. Using chloroacetaldehyde as raw material, using sodium bisulfite to reduce and then react with alkali to generate sodium α-amino-β-chloroacetane sulfonate, and further cyanide with sodium cyanide to prepare α-amino-β-Chloropropiononitrile is finally prepared by acrylonitrile method. 6. α-isocyanacetamide reacts with formaldehyde to form quinazoline intermediate, which is prepared by direct hydrolysis. 7, electrolytic reduction method. First, the ethyl propionamide is oxidized to the corresponding oxime, and then lithium chloride is used as the supporting electrolyte, and the two poles are lead and platinum, which can be produced by electrolytic reduction. 8. Ethanolamine is used as raw material, oxidized with hydrogen peroxide under the action of catalyst sodium tungstate, and then cyanated by sodium cyanide to generate aminonitrile, and finally hydrolyzed in hydrochloric acid to prepare DL-Serine. |
| amino acid composition of mulberry leaf protein and silkworm body protein | the amino acid composition of mulberry leaf protein and silkworm body protein is different, mainly the 6 content percentages of alanine, methionine, glycine, tyrosine, phenylalanine and proline in silkworm body protein are more than mulberry leaf protein, especially methionine as an essential amino acid, silkworm body protein is as much as 2.7 times higher than mulberry leaf protein, it must be accumulated from a large amount of food under eating. Other non-essential amino acids can be produced in the silkworm except for mulberry leaves. The cocoon silk protein produced in the silkworm body is different from the silkworm body protein. The content percentage of non-essential amino acids such as glycine, alanine, serine and tyrosine is significantly larger. The total of these four amino acids is 79.68%, while the silkworm body protein only accounts for 43.26%, especially the increase of serine is the largest. It can be seen that the generation of cocoon silk protein is not derived from silkworm body protein, but is directly synthesized in silk gland cells with free amino acids in blood as materials. The large increase in alanine and glycine in the silkworm can transfer the amino group from another amino acid (glutamic acid or aspartic acid) to pyruvate or glyoxylic acid with the participation of transaminase. Alanine can be produced under the successive action of glutamic transaminase, oxaloacetate decarboxylase and glutamic-pyruvic transaminase. It can also be produced by ornithine transaminase (Xu Tingsen et al., 1980). Silk gland tissue can use ketomalonic acid as the amino receptor to undergo transamination to generate aminomalonic acid, and then under the catalysis of aminomalonic acid decarboxylase, glycine is generated (Zou Baixiang et al., 1979). Glycine can be transformed with serine, glucose can also produce serine through 3-phosphate hydroxypyruvate, and serine can produce alanine through pyruvate. Tyrosine can be produced by phenylalanine, cystine can be produced by methionine transformation but not the opposite transformation, so phenylalanine and methionine are essential amino acids. When the feed is rich in tyrosine and cystine, the requirement of phenylalanine and methionine can be reduced. |
| identification test | take 5ml of 0.1% sample solution and add lml of ninhydrin test solution (TS-250), which should be blue-purple or purple. |
| content analysis | accurately weigh the sample about 200mg and dissolve in 3ml formic acid and 50ml glacial acetic acid. Titration with 0.1mol/L perchloric acid glacial acetic acid solution, the end point was determined by potentiometer. At the same time, blank test and necessary correction are made. 0.1mol/L perchloric acid per ml is equivalent to 10.5lmg of DL-serine (C3H7NO3). |
| use | used for biochemical research, preparation of tissue culture medium, and used as amino acid nutrition medicine in medicine. Nutritional supplements. Used as biochemical reagent Pharmaceutical intermediate or API. |
| production method | is obtained by complexing glycine under copper ion catalysis and then combining with formaldehyde under alkaline conditions, then acidification, ion exchange and crystallization in ethanol. In the presence of excessive copper carbonate, formaldehyde and glycine are used as raw materials to reflux, and after cooling, filtration, acidification, column chromatography, and crystallization are used to obtain the product. |
Last Update：2024-04-09 21:32:05
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