(2S,3S)-a-Amino-b-methylvaleric acid
L-Isoleucine
CAS: 73-32-5;131598-62-4
Molecular Formula: C6H13NO2
(2S,3S)-a-Amino-b-methylvaleric acid - Names and Identifiers
| Name | L-Isoleucine |
| Synonyms | Ile L-Ile L-Ile-OH H-Ile-OH Isoleucine Isoleucina Isoleucinum iso-leucine L-Isoieucine L-ISOLEUSINE L-Isoleucine Isoleucine, L- L-(+)-Isoleucine Isoleucine (USP) (2S,3S)-(+)-Isoleucine 2-Amino-3-methylvaleric acid L-(+)-Isoleucine, Animal-Free L-2-Amino-3-methylvaleric Acid (2S,3S)-2-Amino-3-methylpentansαure 6-Amino-5-ethylamino-1-methyluracil (2S)-2-Amino-3-methylpentanoic acid (2S,3S)-a-Amino-b-methylvaleric acid (2S,3S)-2-amino-3-methyl-Pentanoic acid (2S,3S)-a-Amino-b-methyl-n-valeric acid (2s,3s)-alpha-amino-beta-merthylvalericacid (2s,3s)-alpha-amino-beta-methyl-n-valericacid |
| CAS | 73-32-5 131598-62-4 |
| EINECS | 200-798-2 |
| InChI | InChI=1/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 |
| InChIKey | AGPKZVBTJJNPAG-WHFBIAKZSA-N |
(2S,3S)-a-Amino-b-methylvaleric acid - Physico-chemical Properties
| Molecular Formula | C6H13NO2 |
| Molar Mass | 131.17 |
| Density | 1.2930 (estimate) |
| Melting Point | 288 °C (dec.) (lit.) |
| Boling Point | 225.8±23.0 °C(Predicted) |
| Specific Rotation(α) | 41 º (c=4, 6N HCl) |
| Flash Point | 168-170°C |
| JECFA Number | 2118 |
| Water Solubility | 41.2 g/L (50 ºC) |
| Solubility | The solubility in water is 4.12%, which is extremely difficult to dissolve in ethanol and ether. |
| Appearance | White crystal or crystalline powder |
| Color | White to Off-white |
| Maximum wavelength(λmax) | λ: 260 nm Amax: 0.07λ: 280 nm Amax: 0.05 |
| Merck | 14,5179 |
| BRN | 1721792 |
| pKa | 2.32, 9.76(at 25℃) |
| PH | 5.5-6.5 (40g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 40.5 ° (C=4, 6mol/L |
| MDL | MFCD00064222 |
| Physical and Chemical Properties | Melting point 168-170°C sublimation point 168-170°C specific optical rotation 41 ° (c = 4, 6N HCl) water-soluble 41.2g/L (50°C) |
| Use | Used as amino acid injection, compound amino acid infusion, food additives |
(2S,3S)-a-Amino-b-methylvaleric acid - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 40 - Limited evidence of a carcinogenic effect |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | NR4705000 |
| TSCA | Yes |
| HS Code | 29224995 |
| Toxicity | LD50 intraperitoneal in rat: 6822mg/kg |
(2S,3S)-a-Amino-b-methylvaleric acid - Upstream Downstream Industry
| Raw Materials | Dextrose Anhydrate Ammonia |
(2S,3S)-a-Amino-b-methylvaleric acid - Nature
Open Data Verified Data
This product is white crystal or crystalline powder; Odorless, slightly bitter taste. Melting point 284 C (decomposition),168~170 C sublimation. Slightly soluble in water (4.12%,25 °c), practically insoluble in ethanol and ether. It is an essential amino acid, is one of the three branched chain amino acids, oxidative decomposition can release more energy, per mole of isoleucine can produce 43mol ATP. The metabolic site is mainly in the muscle, which is a sugar and ketogenic amino acid. The metabolic process not only releases acetyl CoA, but also generates succinic acid. It has the effect of promoting insulin secretion. Lack of L-isoleucine can cause skeletal muscle disorders. It has a competitive inhibitory effect with the other two branched chain amino acids.
Last Update：2024-01-02 23:10:35
(2S,3S)-a-Amino-b-methylvaleric acid - Preparation Method
Open Data Verified Data
fermentation method
Last Update：2022-01-01 11:10:04
(2S,3S)-a-Amino-b-methylvaleric acid - Use
Open Data Verified Data
amino acid drugs. For nutritional supplements, mixed with other carbohydrates, inorganic salts and vitamins for injection. Compatibility with other amino acids for amino acid infusion and preparation.
Last Update：2022-01-01 11:10:04
(2S,3S)-a-Amino-b-methylvaleric acid - Safety
Open Data Verified Data
- when amino acids are supplemented, an appropriate ratio of isoleucine to other chloro-based acids is maintained. If the amount of isoleucine used is too large, a nutritional counteraction is generated, causing consumption of other amino acids and negative nitrogen balance.
- adult instillation of 15g at a time can cause Fever reaction and Head Pain, back pain. The patient was kept under closed storage.
Last Update：2022-01-01 11:10:05
(2S,3S)-a-Amino-b-methylvaleric acid - Reference Information
| properties | white crystalline powder |
| properties | white crystalline small piece or crystalline powder. Slightly bitter. Odorless. |
| use | l isoleucine as nutritional supplement. amino acid drugs. It is a nutritional supplement, mixed with other carbohydrates, inorganic salts and vitamins for injection. Compatible with other amino acids for amino acid infusion and preparation. Adverse reactions and contraindications: When supplementing amino acids, the supplemented isoleucine and other amino acids are required to maintain an appropriate proportion. If the amount of isoleucine is too large, it will produce nutritional antagonism, causing the consumption of other amino acids and negative nitrogen balance. It is used for biochemical research and for nutritional supplements in medicine. Nutritional supplements. One of the essential amino acids, the minimum daily requirement is about 0.7g. It can be fortified with various foods, such as wheat flour, gluten, peanut powder, potato, etc., which contain isoleucine as a limiting amino acid and should be fortified. It can also be used in amino acid preparations and amino acid infusion with other essential amino acids. Nutritional supplements. L-isoleucine is one of the essential amino acids for the human body. The minimum daily requirement is about 0.7g, but excessive consumption will antagonize leucine and hinder development. This product can strengthen various foods, such as wheat flour, gluten, peanut powder, potato, etc., which contain isoleucine as a limiting amino acid and should be fortified. The product is also used for amino acid preparation and amino acid infusion with other essential amino acids. The product is also used in biochemical research, bacteriology and tissue culture. used as amino acid injection, compound amino acid infusion, food additive |
| application | since l-isoleucine cannot be synthesized in human body, it is an essential amino acid for human body, and is collectively referred to as branched chain amino acid with l-leucine and l-valine, because of its special structure and function, it plays an important role in human life metabolism. |
| principle of action | can strengthen various foods, such as wheat flour, gluten, peanut flour, potato, etc., which contain isoleucine as a limiting amino acid and should be strengthened. It can be combined with essential amino acids in amino acid preparations and amino acid infusion. |
| chemical properties | is white crystal or crystalline powder, odorless and slightly bitter taste. Mp284 ℃ (decomposition), 168-170 ℃ sublimation. The solubility in water is 4.12%, extremely insoluble in ethanol and ether, [α]25D +39.5 (C = 0.5-2.0 g/ml, 5mol/L HCl), [α]25D +12.4 (C = 0.5-2.0 g/ml, H2O), isoelectric point pI is 6.02. |
| production method | using sugar, ammonia, and D-threonine as raw materials, obtained by fermentation of Cytella mucilaginii (Serratia marcescens). Or using sugar, ammonia, and α-aminobutyric acid as raw materials, fermented with Micrococcus flavum or Bacillus subtilis (Bacillus subtilis;Aerobactor). sugar, ammonia and D-threonine were used as raw materials and fermented by Cyrtella muccensis (Serratia marcescens). the final concentration of fermentation broth was 0.5~1.5g/100ml. Or sugar, ammonia and α-aminobutyric acid are used as raw materials and fermented with Micrococcus flavum or Bacillus subtilis (Bacillus subtilis, Aerobactor). The final concentration of the fermentation broth can reach 1.0~1.5g/100ml. using D-isoleucine as raw material, acylation reaction with acetic anhydride, the product is obtained by hydrolysis after separation of D-isoleucine by acylase treatment. α-acetolactate synthase [culture solution (strain culture)]→ strain amplification culture [fermentation] →[30-31 ℃, 60h] fermentation broth [filtration] → [heating] upper liquid [oxalic acid, sulfuric acid (acidification)]→ [filtration] filtrate [H +732 resin] →[(adsorption separation)] eluent [concentration] → [decompression distillation] concentrated solution [NH3 water (neutralization)]→ precipitation [water (refining)]→ crystallization [105 ℃ drying] → L-isoleucine finished strain culture seed culture medium the composition is glucose 2%, urea 0.3%, corn steep liquor 2.5%, bean cake hydrolysate 0.1% (based on dried bean cake), pH 6.5, heat preservation 118-120 ℃, sterilization for 30min. Primary seed culture. Add 200ml of the above culture medium into a 1000ml conical flask, inoculate a ring of beef paste inclined plane AS (I .e. α-acetolactate synthase) 1.998 strains, culture at 30 ℃, stroke 7cm, frequency 105 times/min, 16h. Secondary seed culture. The secondary seed medium is similar to the primary seed medium, plus rapeseed oil 0.4%, the inoculation amount is 3.5%, and the culture is 8 hours, so that sufficient strains are gradually enlarged and cultured. The fermentation and acidification fermentation broth is composed of ammonium sulfate 4.5%, soybean cake hydrolysate 0.4%, corn steep 2.0%, calcium carbonate 4.5%, pH adjusted to 7.2, and initial sugar concentration 11.5 of starch hydrolyzed reducing sugar. Then 3t of the above fermentation broth is added to a 5m3 fermentation tank, heated at 118-120 ℃, controlled at a pressure of 1.1 × 105Pa, immediately cooled to 25 ℃ by ice brine after 30min of sterilization, 1% strains are added, heated at 180r /min, heated at 30-31 ℃, fermented at 0.21L/min aeration for 60h, and continuously added urea to 0.6% and ammonia to 0.27% between 24-50h. After 60h of fermentation, the fermentation broth was heated to 100 ℃ and kept for 10min. After cooling, filter, remove thallus, filtrate processing industry with ammonium sulfate and oxalic acid to pH3.5, filter to take filtrate. After separating and concentrating the filtrate flowing through the hydrogen type 732 ion exchange resin (400mm × 1000mm) at a flow rate of 1.5% resin amount per minute, the resin column is washed with 100L deionized water, and finally elution is carried out at a flow rate of 3L/min with 0.5mol/L ammonia water at 60 ℃, and the eluent is collected step by step. The eluent with a combined pH of 3-12 was distilled and concentrated to viscous at 70-80°C under reduced pressure. Add deionized water to 1/4 of the original volume, then concentrate to a viscous shape, and catch ammonia, and repeat this three times. Decolorization, Concentration and Neutralization Add deionized water to 1/4 of the original volume of the above concentrated viscous substance, stir evenly, add 2mol/L HCl to adjust the pH to 3.5, then add 1% activated carbon, keep the temperature at 70-80 ℃ for decolorization for 1h, filter to obtain filtrate and concentrate under reduced pressure, finally add 2mol/L HCl to adjust the pH to 6.0, keep the temperature at 5 ℃, and let the precipitation stay overnight, the precipitate is filtered and dried at 105 ℃ to obtain semi-finished products. Refined 10kg of semi-finished products, add 8L of concentrated hydrochloric acid and 20L of deionized water, heat and stir to dissolve them, then add 10kg NaCl to saturation, adjust pH to 10.5 of alkali in processing industry, filter to take filtrate, add alkali to adjust pH to 1.5, hold the temperature at 5 ℃ for overnight precipitation, filter to take precipitate, heat and stir with 80L deionized water to dissolve them, add appropriate amount of NaCl and 1% activated carbon, stir at 70-80 ℃ for decolorization for 1h, filter to take filtrate, concentrate to an appropriate concentration under reduced pressure, adjust pH to 6.0 with ammonia water, hold the temperature at 5 ℃ for overnight precipitation and crystallization, filter to take crystallization, and dry at 105 ℃ to obtain L-isoleucine finished product. |
| NIST chemical information | The information is: webbook.nist.gov provides (external link) |
| EPA chemical information | The information is: ofmpub.epa.gov provides (external link) |
| toxic substance data | The information is: pubchem.ncbi.nlm.nih.gov Provide (external link) |
Last Update：2024-04-09 20:49:11
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Raw Materials for (2S,3S)-a-Amino-b-methylvaleric acid