609-36-9
DL-Proline
CAS: 609-36-9
Molecular Formula: C5H9NO2
609-36-9 - Names and Identifiers
| Name | DL-Proline |
| Synonyms | DL-Pro-OH DL-PROLINE DL-Proline H-DL-Pro-OH H-DL-PRO-OH H-DL-PYRD(2)-OH LABOTEST-BB LTBB000673 ProlinePyrrolidinecarboxylicacid |
| CAS | 609-36-9 |
| EINECS | 210-189-3 |
| InChI | InChI=1/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8) |
609-36-9 - Physico-chemical Properties
| Molecular Formula | C5H9NO2 |
| Molar Mass | 115.13 |
| Density | 1.1808 (rough estimate) |
| Melting Point | 208 °C (dec.) (lit.) |
| Boling Point | 215.41°C (rough estimate) |
| Water Solubility | SOLUBLE |
| Solubility | Methanol, Water |
| Appearance | Colorless crystal |
| Color | White to off-white |
| Merck | 14,7780 |
| BRN | 80809 |
| pKa | 2.35±0.20(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.4538 (estimate) |
| MDL | MFCD00005250 |
| Physical and Chemical Properties | Colorless crystal, odorless, sweet, easy to deliquescence; Soluble in water and ethanol, insoluble in chloroform and acetone, insoluble in butanol and ether; Decomposition point of 205 ℃. |
| Use | Used for biochemical and nutritional research, microbiological test, preparation of culture medium. |
609-36-9 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 3-10 |
| TSCA | Yes |
| HS Code | 29339990 |
609-36-9 - Introduction
It is deliquescent. Soluble in water and alcohol, insoluble in acetone, benzene and chloroform, insoluble in ether.
Last Update：2022-10-16 17:27:01
609-36-9 - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | DL-proline, Proline (abbreviated as Pro or P), alpha-amino acids, neutral, isoelectric point of 6.30, water solubility than any amino acids are large, 25 ℃ 100g water soluble about 162g. Easy to deliquescence is not easy to get Crystal, there is a sweet taste. Co-heating with ninhydrin solution to form a yellow compound. Once in the peptide chain, can occur hydroxylation, thereby forming 4-hydroxyproline, is an important component of animal collagen. Hydroxyproline is also present in a variety of plant proteins, particularly in relation to cell wall formation. Plants in drought, high temperature, low temperature, salt and other stress, often have obvious accumulation of proline. In clinical, biological materials, industrial and other aspects have been widely used. We know that there are three forms of proline DL-proline, L-proline, D-proline, generally known as proline is L-proline, a naturally occurring amino acid, room temperature this product is columnar crystals. It decomposes rapidly when heated to 215-220 °c. Soluble in hot water and ethanol. Micro-sweet, hygroscopic. Racemization in alkaline solution. [Α] D25-86.5 ° (water), -60.4 °(5N hydrochloric acid). Distributed in a variety of proteins. An amino acid found in marine plankton; It is also found in seawater, particulate matter, and marine sediments. scientific name of proline (Pro): pyrrolidone carboxylic acid. A cyclic imino acid; The only imino acid among the 20 common amino acids that make up a protein. In the peptide chain has its special role, easy to form CIS peptide bond, is not conducive to the formation of alpha helix |
| application field | 1, the pharmaceutical industry application of amino acid drugs. Compound amino acid infusion of one of the raw materials. Protein supplement for malnutrition, protein deficiency, severe gastrointestinal diseases, Burns and after surgery. No obvious side effects. 2, improve plant cold resistance proline (Pro) is one of the components of plant protein, and can be widely present in the Free State in plants. Proline is accumulated in many plants under drought and salt stress conditions. In addition to the accumulation of proline as a plant cytoplasmic osmotic adjustment, but also in the stability of biological macromolecular structure, reduce cell acidity, it plays an important role in relieving ammonia toxicity and regulating cell redox potential as an energy sink. Under stress conditions (drought, salt, heat, cold, freezing), the content of proline in plants increased significantly. The proline content in plants reflects the stress resistance of plants to some extent, and the varieties with strong drought resistance tend to accumulate more proline. Therefore, the determination of proline content can be used as a physiological index of drought resistance breeding. In addition, because proline is highly hydrophilic, it can stabilize the metabolic process in the plasma colloid and tissue, thus reducing the freezing point and preventing the dehydration of cells. Under the condition of low temperature, the increase of proline in plant tissues can improve the cold resistance of plants. Therefore, it can also be used as a physiological index of cold resistance breeding. 3, the biological role in vivo, proline is not only an ideal osmotic adjustment material, but also can be used as a membrane and enzyme protection material and free radical scavenger, so as to protect the growth of plants under osmotic stress, for the accumulation of another important osmotic regulator in the vacuole of potassium ion, proline can also play a role in regulating the osmotic balance of cytoplasm. 4, industrial applications in the synthesis industry, proline can be involved in the induction of asymmetric reactions, can be used as a catalyst for hydrogenation, polymerization, water and other reactions, it is used as a catalyst for such reactions, It has the characteristics of strong activity and good stereo specificity. 5. Other applications 5.1 proline and its derivatives are generally used as symmetric catalysts in organic reactions, with the reduction of CBS and the aldol condensation reaction catalyzed by proline being prominent examples. 5.2 in brewing, protein is rich in proline combined with polyphenols, which can produce haze (turbidity). 5.3 Synthesis of bile gangue Ester inhibitor raw materials. 5.4 flavor, and Sugar Co-heat amino light base reaction, can be generated with a special flavor of the material. |
| metabolic process | glutamic acid produces glutamyl phosphate (γ-GP) under the action of γ-GK, then in the role of glutamic acid half aldehyde dehydrogenase (GSADH) to produce glutamic acid half aldehyde (GSA),GSA spontaneous cyclization of pyrrolin-5-carboxylic acid (P5C), reduction to proline by pyrrolin-5-carboxylic acid reductase (P5CR). The degradation of proline in plants is basically the reverse process of the synthesis process, which first occurs in the mitochondria. Proline is catalyzed by proline dehydrogenase (ProDH) in the mitochondria to generate P5C, p5C produces glutamic acid under the action of pyrroline-5-carboxylic acid dehydrogenase (P5CDH). When plants are under osmotic stress, the process of oxidative degradation is inhibited, so that the amount of proline in cells increases, plant rehydration is that this process is again induced, resulting in a decrease in proline content. |
| preparation | 100g of glacial acetic acid was added to the reaction vessel, and then 100g of L-proline was added with stirring to obtain a reaction solution. The reaction solution was stirred and heated to 70-75 ° C., and then the temperature was maintained and stirred for 3H so that L-proline was sufficiently racemic, and the optical rotation of the reaction solution was 0, and the reaction solution was red-brown in color. After the reaction solution with optical rotation of 0 is cooled to 30 ° C., it is transferred to a distillation kettle for vacuum distillation at a temperature of 55-60 ° C. And a steam pressure of 0.1MPa, the distillation was continued for another 30min after the distillation to no liquid outflow, and then the distillation residue was concentrated to 10% of the original volume to give A viscous concentrated liquid A. The concentrated solution A was mixed with 120g of isopropanol, stirred until the crystals were completely precipitated, and then cooled to 15 ° C., centrifuged to remove excess liquid, and the crystals were rinsed with isopropanol to obtain A crude product. After mixing 90g of crude product, 5g of activated carbon and 185g of water, the mixture was stirred and heated to 70 ° C., and stirred for 30min to completely dissolve the crude product, and then filtered to remove the activated carbon. The residue without activated carbon after filtration was concentrated to 20% of the original volume to give a viscous concentrate B. Concentrate B was mixed with 285g isopropanol, stirred until the crystals were completely precipitated, then cooled to 15 ° C., centrifuged to remove excess liquid, and the crystals were rinsed with isopropanol, after rinsing, the crystals were dried at 80 °c for 12h to obtain a sample of DL-proline. |
| synthesis process | There are two ways to synthesize proline in plants: one way is to synthesize proline with glutamic acid (Glu) as substrate, another pathway is the synthesis of proline by ornithine as a substrate, usually in the case of plant stress or nitrogen deficiency, the main source of proline is the glutamate synthesis pathway, in the case of adequate nitrogen supply, the main synthesis pathway of proline in plants is the synthesis of ornithine as a substrate. |
| trait | white powder |
| properties | proline is white crystal or crystalline powder; It is slightly odorous, slightly sweet, Melting Point: 210-220°C, deliquescent, soluble in water, soluble in ethanol, insoluble in acetone and chloroform in ether or n-butanol insoluble. |
| Use | Nutrition Fortifier, used for biochemical and nutritional research, microbial test, medium was prepared for biochemical studies. used in biochemical and nutritional research, microbial testing, preparation of culture medium. |
| production method | L-proline is used as raw material to be acetylated and refined. |
Last Update：2024-04-09 20:49:11
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