dl-methionine
DL-Methionine
CAS: 59-51-8
Molecular Formula: C5H11NO2S
dl-methionine - Names and Identifiers
| Name | DL-Methionine |
| Synonyms | Neston Metione Urimeth Pedameth Petameth Thiomedon H-DL-Met-OH DL-Methionine DL-Methoionine (RS)-2-Amino-3-methylthiobutansαure DL-2-Amino-4-(methylthio)butyric acid (R,S)-2-Amino-4-methylsulfanyl-butyricacid |
| CAS | 59-51-8 |
| EINECS | 200-432-1 |
| InChI | InChI=1/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8) |
| InChIKey | FFEARJCKVFRZRR-UHFFFAOYSA-N |
dl-methionine - Physico-chemical Properties
| Molecular Formula | C5H11NO2S |
| Molar Mass | 149.21 |
| Density | 1.34 |
| Melting Point | 284°C (dec.)(lit.) |
| Boling Point | 306.9±37.0 °C(Predicted) |
| Specific Rotation(α) | -1～+1°(D/20℃)(c=8,HCl) |
| JECFA Number | 1424 |
| Water Solubility | 2.9 g/100 mL (20 ºC) |
| Solubility | Soluble in water, dilute acid and dilute alkali, slightly soluble in 95% alcohol, insoluble in ether |
| Appearance | Crystalline powder |
| Color | White |
| Merck | 14,5975 |
| BRN | 636185 |
| pKa | 2.13(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidising agents. |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5216 (estimate) |
| MDL | MFCD00063096 |
| Physical and Chemical Properties | White flaky crystal or crystalline powder. Special odor. The taste was slightly sweet. Melting point 281 degrees (decomposition). 10% pH of the aqueous solution 5.6-6.1. No optical rotation. Stable to heat and air. Unstable to strong acids, can lead to demethylation. Soluble in water (3.3g/100ml,25 degrees), dilute acid and dilute solution. Extremely insoluble in ethanol, almost insoluble in ether |
| Use | Used as a Biochemical reagent |
dl-methionine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R33 - Danger of cumulative effects R36/37/38 - 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 | 2 |
| RTECS | PD0457000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29304090 |
dl-methionine - Reference
| Reference Show more | 1. Li Yuanyuan, Han Lihua, Ju Hao, et al. Ameliorative effect of sea cucumber glue on chronic inflammation in insulin resistance model mice [J]. China Marine Medicine, 2018, v.37;No.182(02):32-38. 2. Wei Shuyan, Xiao Liubin, Tan Yongan, etc. Changes of physiological and metabolic indexes in transgenic Bt cotton and conventional cotton after being damaged by medium black bug [J]. Journal of Nanjing Agricultural University, 2010, 33(005):55-59. 3. Qiu Zhen, Yu, fan, Li, Guo, Zhi, et al. Effects of sweating in different environments on the content of effective components and antioxidant activity of Salvia miltiorrhiza Bunge [J]. Natural product research and development 2017(10):82-86 114. 4. 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). 5. Yang, X., sun, X., feng, Z. et al. Open-tubular capillary electrochromatography with β-cyclodextrin-functionalized magnetic nanoparticles as stationary phase for enantioseparation of dansylated amino acids. Microchim Acta 186, 244 (2019). https://doi.org/1 6. Liu, Changhe, et al. "Metformin regulates the expression of SK2 and SK3 in the atria of rats with type 2 diabetes mellitus through the NOX4/p38MAPK signaling pathway ." Journal of cardiovascular pharmacology 72.5 (2018): 205-213.10.1097/FJC.0000000000000615 7. Xinru Xu, Mingguang Yu, Junaid Raza, Huanlu Song, Lin Gong, Wenqing Pan, Study of the mechanism of flavor compounds formed via taste-active peptides in bovine bone protein extract, LWT, Volume 137, 2021, 110371, ISSN 0023-6438, https://doi.org/10.1016/j.lw 8. Qu Fei, et al. "Fluorescent Detection of 2, 4-Dichlorophenoxyacetic Acid in Food Samples Based on Covalent Organic Frameworks and MnO 2 Nanosheets." Food Analytical Methods 13.10 (2020): 1842-1851.https://doi.org/10.1007/s12161-020-01807-2 9. [IF=5.833] Yang Xuan et al."Open-tubular capillary electrochromatography with β-cyclodextrin-functionalized magnetic nanoparticles as stationary phase for enantioseparation of dansylated amino acids."Microchim Acta. 2019 Apr;186(4):1-8 10. [IF=6.057] Chenglong Sun et al."1,1′-binaphthyl-2,2′-diamine as a novel MALDI matrix to enhance the in situ imaging of metabolic heterogeneity in lung cancer."Talanta. 2020 Mar;209:120557 11. [IF=5.537] Yurong Ma et al."Pre-cut NaCl solution treatment effectively inhibited the browning of fresh-cut potato by influencing polyphenol oxidase activity and several free amino acids contents."Postharvest Biol Tec. 2021 Aug;178:111543 12. [IF=4.952] Huan Zhang et al."Label-free quantification proteomics reveals the active peptides from protein degradation during anaerobic fermentation of tea."Lwt Food Sci Technol. 2021 Oct;150:111950 13. [IF=4.821] Peng Wan et al."Analysis of aroma-active compounds in bighead carp head soup and their influence on umami of a model soup."Microchem J. 2021 Sep;168:106436 14. [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 15. [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 16. [IF=2.352] Man Lyu et al."Inhibition effect of thiol-type antioxidants on protein oxidative aggregation caused by free radicals."Biophys Chem. 2020 May;260:106367 17. [IF=1.618] Wang Shengnan et al."Simultaneous Determination of Iridoid Glycosides, Phenylpropanoid Glycosides, Organic Acids, Nucleosides and Amino Acids in Scrophulariae Radix Processed by Different Processing Methods by HPLC-QTRAP-MS/MS."J Chromatogr Sci. 2021 Jun; 18. [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 19. [IF=7.514] Shibin Deng et al."Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model."Food Chem. 2022 Jul;382:132500 20. [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 |
dl-methionine - Nature
Open Data Verified Data
white crystalline powder, a slight special odor of sulfur compounds, slightly sweet taste. Soluble in water, dilute acid and dilute alkali, difficult to dissolve in ethanol, ether and other organic solvents. The pH value of the 1% aqueous solution was 5.6-6.1. Stable to heat and air, unstable to strong acid.
Last Update：2024-01-02 23:10:35
dl-methionine - Preparation Method
Open Data Verified Data
with acrolein as raw material synthesis.
Last Update：2022-01-01 10:10:34
dl-methionine - Use
Open Data Verified Data
used as a feed Nutrition Fortifier, can make up the balance of amino acids. Lack of methionine in livestock and poultry will cause dysplasia, weight loss, liver and kidney function, muscle atrophy, hair deterioration and so on. Feed added 1kg methionine, equivalent to the nutritional value of 50kg fish meal. The general addition amount is 0.05% ~ 0.2%.
Last Update：2022-01-01 10:10:35
dl-methionine - Safety
Open Data Verified Data
hepatic coma. The patient was kept under closed storage.
Last Update：2022-01-01 11:10:29
dl-methionine - Reference Information
| FEMA | 3301 | D,L-METHIONINE |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| properties | DL-methionine is a white flake crystal or crystalline powder. Special odor. The taste was slightly sweet. Melting point 281 degrees (decomposition). 10% pH of the aqueous solution 5.6-6.1. No optical rotation. Stable to heat and air. Unstable to strong acids, can lead to demethylation. Soluble in water (3.3g/100ml,25 degrees), dilute acid and dilute solution. Very difficult to dissolve in ethanol, almost insoluble in ether. |
| Use | DL-methionine may be used as a nutritional supplement. The physiological effect is the same as that of L-type methionine, but the L-type is low in price (L-type is produced by DL-type), so DL-methionine is generally used. In oats, rye, rice, corn, wheat, peanut flour, soybeans, potatoes, spinach and other plant-based foods to improve amino acid balance. applicable to the prevention and treatment of liver disease and arsenic or benzene poisoning, can also be used for the treatment of dysentery and chronic infectious diseases caused by protein deficiency after malnutrition This product is a feed Nutrition Fortifier. Lack of methionine in livestock and poultry will cause dysplasia, weight loss, liver and kidney function, muscle atrophy, fur deterioration and so on. Feed added 1kg methionine, equivalent to the nutritional value of 50kg fish meal. The general amount of feed is 0,05%-0.2%. nutritional supplements. The physiological effect is the same as that of L-type methionine, but the L-type is low in price (L-type is produced by DL-type), so DL-methionine is generally used. In oats, rye, rice, corn, wheat, peanut flour, soybeans, potatoes, spinach and other plant-based food belonging to the restriction of amino acids. Added to the above foods to improve the amino acid balance. Requirements vary with cystine intake. The requirement for an adult male is 1.1g/d. Sea urchin and methionine related, sea urchin sweet and glycine, alanine related, bitter and valine related, flavor and glutamic acid and so on, so these amino acids can be formulated into flavoring agent. Still used for amino acid infusion, comprehensive amino acid preparation. According to China GB 2760-86 regulations can be used as spices. The content of commercial methionine is more than or equal to 98.5%, which is one of the essential amino acids for the growth of livestock and animals, and is the "skeleton" amino acid of biosynthetic protein, which has a strong regulatory effect on the metabolism of animals, widely used in medicine, food, feed and cosmetics and other fields. Which in medicine, can be used as the main component of amino acid infusion and compound amino acids, can also be used for the synthesis of medicinal vitamins, the use of its anti-fatty liver, can be used for the production of liver preparations; In food, for food amino acid fortification and processing of food and health products, can be used as nutritional supplements, due to special odor, so only for fish cake products; In the feed industry, the largest amount of methionine, used as feed Nutrition Fortifier, make up the balance of amino acids in feed additives, amino acid nutrition feed additives in varieties, methionine 60%, lysine accounted for 30%, other amino acids accounted for about 10%. used as a Biochemical reagent biochemical studies; Used in the culture of mammalian and insect cells with mixed isomers |
| range of use | adult male requirement: 1G/d. Can be safely used in food. It accounts for 3.1% of the total protein in food. Not for infants and young children food. |
| principle of action | DL-methionine is one of the essential amino acids for human body, and deficiency can cause liver and kidney disorders. It is especially important for the protection of liver function. Can promote hair, nail growth, and detoxification and enhance muscle activity and other effects. |
| content analysis | a sample of approximately mg was accurately weighed and transferred into a stopcock flask. Add 100ml of water, 5g of Dipotassium hydrogen phosphate, 2g of potassium dihydrogen phosphate and 2g of potassium iodide, and mix well until dissolved. Then 50ml of 0.1mol/L iodine solution was accurately measured, and the flask was closed and mixed. After standing for 30min, the excess iodine was titrated with 0.1mol/L sodium thiosulfate. At the same time, the blank test was carried out and the necessary correction was made. Each MIM 0.1mol/L iodine solution corresponds to 7.461mg of DL-methionine (C5HllNO2S). |
| toxicity | L-type: LD5029mmol/kg (rat, intraperitoneal injection);D-type: LD5035mmol/kg (rat, intraperitoneal injection). Safe for use in food (FDA,§ 172.320,2000). |
| usage limit | FDA,§ 172.320(2000):(1) not for infant food;(2) it accounts for 3.1% of the total protein in food. FEMA: same as "01115, isoleucine". |
| production method | methionine can be prepared by extraction, but there are the following methods in industry: 1. Rhone-Planck process 2. The consumption quota of DL-methionine process raw materials in dpoga: acrolein 480kg/t, methyl mercaptan 400kg/t, sodium cyanide 420kg/t. methionine of the D-configuration and the L-configuration have the same physiological action, and DL-type is often used, so it is advantageous to produce it synthetically. It is generally prepared by reacting acrolein with methyl mercaptan. A synthesis method using an acrylic aldehyde as a raw material is generally used. The condensation of Propylene aldehyde and methyl mercaptan in the presence of formic acid and copper acetate produces 3-methylthiopropionaldehyde. Then mixed with sodium cyanide and ammonium bicarbonate solution. The reaction at 90 °c gave methylthioethyl hydantoin. Without separation and purification, it can be heated with 28% sodium hydroxide solution to 180 C, hydrolysis to form sodium methionine. The final methionine was obtained by neutralization with hydrochloric acid. Each ton of product consumption of acrylic aldehyde 480kg, methyl mercaptan 400kg, sodium cyanide 420kg. |
Last Update：2024-04-09 20:52:54
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dl-methionine
依度沙班杂质F(单体)
CAFTARIC ACID
环庚甲脒盐酸盐
三甲基乙氧基硅烷 危险品
三正丁基溴化锡
16-mercaptohexadecanoic acid solution
依度沙班杂质F(单体)
CAFTARIC ACID
环庚甲脒盐酸盐
三甲基乙氧基硅烷 危险品
三正丁基溴化锡
16-mercaptohexadecanoic acid solution