L-Isoleucine
- Iupac Name：(2S,3S)-2-amino-3-methylpentanoic acid
- CAS No.: 73-32-5
- Molecular Weight：131.17292
- Modify Date.: 2022-11-29 03:19
- Introduction: L-Isoleucine, also known as Isoleucine, is an amino acid that is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training.L-Isoleucine is also classified as a branched-chain amino acid (BCAA). There are three branched-chain amino acids in the body, with the others being L-Valine, and L-Leucine, and all of them help promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue.
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1. Names and Identifiers
- 1.1 Name
- L-Isoleucine
- 1.2 Synonyms
(±)-erythro-2-Amino-3-methylpentanoic acid (±)-Isoleucine (2S,3S)-2-amino-3-methylpentanoic acid (2S,3S)-2-amino-3-methyl-Pentanoic acid (2S,3S)-2-Amino-3-methylpentanoicacid (2S,3S)-2-Amino-3-methylpentansαure (2S,3S)-a-Amino-b-methyl-n-valeric acid (2S,3S)-a-Amino-b-methylvaleric acid (2s,3s)-alpha-amino-beta-merthylvalericacid (2s,3s)-alpha-amino-beta-methyl-n-valericacid (2S,3S)-Ile (S)-isoleucin (S,S)-Isoleucine 2-amino-3-methylpentanoic acid 2-Amino-3-methylvaleric acid a-Amino-b-methylvaleric Acid Acetic acid, amino-sec-butyl- DL-2-Amino-3-methylpentanoic acid DL-Isoleucine EINECS 200-798-2 H-DL-Ile-OH H-ILE-OH H-L-ILE-OH H-lle-OH Ile Isoleucin Isoleucine ISO-LEUCINE Isoleucine, DL- ISOLEUCINE, L- Isoleucine, L- (8CI) L(+)-Isoleucin L-(+)-Isoleucine, Animal-Free L-Ile L-Ile (2S,3S) L-Ile-OH L-Isoieucine L-Isoleucine (JP15) L-Isoleusine MFCD00064222 N-methyl Ile QVYZY2&1 &&(2S,3S)- or L(+)- Form UNII:5HX0BYT4E3 Z-(s,S)-isoleucine
- 1.3 CAS No.
- 73-32-5
- 1.4 CID
- 6306
- 1.5 EINECS(EC#)
- 200-798-2
- 1.6 Molecular Formula
- C6H13NO2 (isomer)
- 1.7 Inchi
- InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1
- 1.8 InChkey
- AGPKZVBTJJNPAG-WHFBIAKZSA-N
- 1.9 Canonical Smiles
- CCC(C)C(C(=O)O)N
- 1.10 Isomers Smiles
- CC[C@H](C)[C@@H](C(=O)O)N
2. Properties
- 2.1 Density
- 1.035
- 2.1 Melting point
- 168-170℃
- 2.1 Boiling point
- 225.8oCat 760 mmHg
- 2.1 Refractive index
- 40.5 ° (C=4, 6mol/L HCl)
- 2.1 Flash Point
- 90.3oC
- 2.1 Precise Quality
- 131.09500
- 2.1 PSA
- 63.32000
- 2.1 logP
- 1.14470
- 2.1 Solubility
- 1 M HCl: 50?mg/mL
- 2.2 Appearance
- White to Off-white powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- White crystalline powder
- 2.5 Color/Form
- White to Off-white
- 2.6 Decomposition
- When heated to decomposition, it emits toxic fumes of /nitric oxide/.
- 2.7 PH
- 5.5-6.5 (40g/l, H2O, 20℃)
- 2.8 pKa
- 2.32, 9.76(at 25℃)
- 2.9 Water Solubility
- H2O: 41.2 g/L (50 oC);1 M HCl: 50?mg/mL
- 2.10 Spectral Properties
- Specific optical rotation: +40.6 at 20 deg C/D (c = 4.6 in 6.1N HCl); 11.09 deg at 20 deg C/D (C = 3.3 in 0.33N NaOH).
MASS: 26148 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 1000 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
IR: 5105 (Coblentz Society spectral collection)
13C NMR: 479 (Stothers, Cabon-13 NMR Spectroscopy, Academic Press, New York)
1H NMR: 16538 (Sadtler Research Laboratories Spectral Collection)
- 2.11 Stability
- Stable under normal temperatures and pressures.
- 2.12 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: The L-enantiomer of isoleucine.
- 3.2 Methods of Manufacturing
- α-Acetolactate Synthase [Culture Solution (Strain Culture)] → Strain Expansion Culture [Fermentation] → [30-31℃, 60h] Fermentation Liquid [Filtration] → [Heating] Upper Layer Liquid [Oxalic Acid, Sulfuric Acid (Acidification) ]→[Filtration] Filtrate [H+732 Resin]→[(Adsorption Separation)] Eluent [Concentrate]→[Vacuum Distillation] Concentrate [NH3 water (neutralization)]→Precipitation [Water (refined)]→ Crystallization [Drying at 105°C]→L-isoleucine finished seed culture medium consists of glucose 2%, urea 0.3%, corn steep liquor 2.5%, soybean cake hydrolysate 0.1% (calculated as dry soybean cake), adjust pH6 .5, keep warm at 118-120℃ and sterilize for 30min.?First-level seed cultivation.?Add 200ml of the above-mentioned medium to a 1000ml conical flask, inoculate a ring of beef extract slant AS (ie, α-acetolactate synthase) 1.998 strain, culture at 30℃, stroke 7cm, frequency 105 times/min, 16h.?Secondary seed cultivation.?The second-level seed medium is similar to the first-level seed medium, with the addition of 0.4% rapeseed oil, an inoculation volume of 3.5%, and cultivation for 8 hours. In this way, a sufficient amount of strains are cultured step by step.?Fermentation and acidification fermentation broth is composed of ammonium sulfate 4.5%, soybean cake hydrolysate 0.4%, corn steep liquor 2.0%, calcium carbonate 4.5%, adjusted pH to 7.2, starch hydrolysis reducing sugar initial sugar concentration 11.5.?Then add the above fermentation broth for 3t in a 5m3 fermentor, heat and keep at 118-120°C, control pressure 1.1×105Pa, sterilize for 30min, immediately cool to 25°C with ice brine, connect 1% strains, 180r/ Stirring and holding at 30-31°C at min speed, fermentation at 0.21L/min aeration for 60h, continuously adding urea to 0.6% and ammonia to 0.27% between 24-50h.?After 60h of fermentation, the fermentation broth was heated to 100°C and held for 10 minutes.?After cooling, filter and remove the bacteria. The filtrate is processed with industrial ammonium sulfate and oxalic acid to pH3.5, and the filtrate is filtered.?After separation and concentration, the above filtrate was flowed through the hydrogen type 732 ion exchange resin (400mm×1000mm) at a flow rate of 1.5% of resin per minute, then the resin column was washed with 100L of deionized water, and finally at 60℃, 0.5mol/L Ammonia is eluted at a flow rate of 3 L/min, and the eluent is collected in steps.?The combined eluates with pH 3-12 were concentrated at 70-80°C under reduced pressure to a viscous state.?Add deionized water to 1/4 of the original volume, and then concentrate to a viscous state, catch ammonia, repeat this three times.?Decolorization, concentration, and neutralization Add deionized water to 1/4 of the original volume of the concentrated viscous material, stir well, and add 2mol/L HCl to adjust the pH to 3.5, then add 1% activated carbon, at 70-80℃ Insulate with stirring and decolorize for 1h. Filter and concentrate the filtrate under reduced pressure. Finally, add 2mol/L HCl to adjust the pH to 6.0. Incubate at 5°C. Leave to settle overnight. Suction and filter the precipitate to dry at 105°C to obtain a semi-finished product.?Refining and taking 10kg semi-finished product, adding 8L concentrated hydrochloric acid, 20L deionized water, heating and stirring to dissolve, then adding 10kg NaCl to saturation, adding industrial alkali to adjust the pH to 10.5, filtering the filtrate, adding alkali to adjust the pH to 1.5, holding 5 Place the precipitate overnight at ℃, filter and collect the precipitate, dissolve with 80L deionized water by heating and stirring, then add appropriate amount of NaCl and 1% activated carbon, stir at 70-80 ℃ for 1h, filter and take the filtrate, concentrate under reduced pressure to the appropriate concentration, use Adjust the pH to 6.0 with ammonia, incubate at 5°C overnight to precipitate the crystals, filter the crystals, and dry at 105°C to obtain the finished L-isoleucine.
- 3.3 Purification Methods
- Crystallise L-isoleucine from H2O by addition of 4 volumes of EtOH or from aqueous MeOH. It sublimes at 170-181o/0.3mm with 99.7% recovery, unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 1 p 183-191, Vol 3 pp 2043-2073 1961, Huffman & Ingersoll J Am Chem Soc 73 3366 1951, Beilstein 4 IV 2775.] L-Isoleucine Preparation Products And Raw materials Raw materials
- 3.4 Usage
- L-Isoleucine, also known as Isoleucine, is an amino acid that is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training.L-Isoleucine is also classified as a branched-chain amino acid (BCAA). There are three branched-chain amino acids in the body, with the others being L-Valine, and L-Leucine, and all of them help promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue.
4. Safety and Handling
- 4.1 Hazard Codes
- Xn
- 4.1 Risk Statements
- R40
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- L-Isoleucine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: isoleucine is included in weight control drug products.
Isoleucine used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
- 4.2 Octanol/Water Partition Coefficient
- log Kow = -1.72
- 4.3 DisposalMethods
- SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
- 4.4 RIDADR
- NONH for all modes of transport
- 4.4 WGK Germany
- 3
- 4.4 RTECS
- NR4705000
- 4.4 Safety
- Hazard Codes:Xn
Risk Statements:40
40:Limited evidence of a carcinogenic effect
Safety Statements:24/25-36-22
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
22:Do not breathe dust
WGK Germany:3
HS Code:29224995
- 4.5 Specification
-
White crystalline powder
Safety Statements:24/25-36-22
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
22:Do not breathe dust
- 4.6 Toxicity
- LD50 intraperitoneal in rat: 6822mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
73-32-5Total: 97 Synthesis Route
9. Other Information
- 9.0 Usage
- L-Isoleucine acts as an essential amino acid in human. It is used as a flavoring agent and nutritional supplement for foods. It is also used as an antipsychotic. It is employed as a component of proteins. Further, it stimulates immune function and promotes secretion of several hormones. In addition to this, it is used for hemoglobin formation and regulating blood sugar and energy levels.
- 9.1 Storage Conditions
- α-Acetolactate Synthase [Culture Solution (Strain Culture)] → Strain Expansion Culture [Fermentation] → [30-31℃, 60h] Fermentation Liquid [Filtration] → [Heating] Upper Layer Liquid [Oxalic Acid, Sulfuric Acid (Acidification) ]→[Filtration] Filtrate [H+732 Resin]→[(Adsorption Separation)] Eluent [Concentrate]→[Vacuum Distillation] Concentrate [NH3 water (neutralization)]→Precipitation [Water (refined)]→ Crystallization [Drying at 105°C]→L-isoleucine finished seed culture medium consists of glucose 2%, urea 0.3%, corn steep liquor 2.5%, soybean cake hydrolysate 0.1% (calculated as dry soybean cake), adjust pH6 .5, keep warm at 118-120℃ and sterilize for 30min.?First-level seed cultivation.?Add 200ml of the above-mentioned medium to a 1000ml conical flask, inoculate a ring of beef extract slant AS (ie, α-acetolactate synthase) 1.998 strain, culture at 30℃, stroke 7cm, frequency 105 times/min, 16h.?Secondary seed cultivation.?The second-level seed medium is similar to the first-level seed medium, with the addition of 0.4% rapeseed oil, an inoculation volume of 3.5%, and cultivation for 8 hours. In this way, a sufficient amount of strains are cultured step by step.?Fermentation and acidification fermentation broth is composed of ammonium sulfate 4.5%, soybean cake hydrolysate 0.4%, corn steep liquor 2.0%, calcium carbonate 4.5%, adjusted pH to 7.2, starch hydrolysis reducing sugar initial sugar concentration 11.5.?Then add the above fermentation broth for 3t in a 5m3 fermentor, heat and keep at 118-120°C, control pressure 1.1×105Pa, sterilize for 30min, immediately cool to 25°C with ice brine, connect 1% strains, 180r/ Stirring and holding at 30-31°C at min speed, fermentation at 0.21L/min aeration for 60h, continuously adding urea to 0.6% and ammonia to 0.27% between 24-50h.?After 60h of fermentation, the fermentation broth was heated to 100°C and held for 10 minutes.?After cooling, filter and remove the bacteria. The filtrate is processed with industrial ammonium sulfate and oxalic acid to pH3.5, and the filtrate is filtered.?After separation and concentration, the above filtrate was flowed through the hydrogen type 732 ion exchange resin (400mm×1000mm) at a flow rate of 1.5% of resin per minute, then the resin column was washed with 100L of deionized water, and finally at 60℃, 0.5mol/L Ammonia is eluted at a flow rate of 3 L/min, and the eluent is collected in steps.?The combined eluates with pH 3-12 were concentrated at 70-80°C under reduced pressure to a viscous state.?Add deionized water to 1/4 of the original volume, and then concentrate to a viscous state, catch ammonia, repeat this three times.?Decolorization, concentration, and neutralization Add deionized water to 1/4 of the original volume of the concentrated viscous material, stir well, and add 2mol/L HCl to adjust the pH to 3.5, then add 1% activated carbon, at 70-80℃ Insulate with stirring and decolorize for 1h. Filter and concentrate the filtrate under reduced pressure. Finally, add 2mol/L HCl to adjust the pH to 6.0. Incubate at 5°C. Leave to settle overnight. Suction and filter the precipitate to dry at 105°C to obtain a semi-finished product.?Refining and taking 10kg semi-finished product, adding 8L concentrated hydrochloric acid, 20L deionized water, heating and stirring to dissolve, then adding 10kg NaCl to saturation, adding industrial alkali to adjust the pH to 10.5, filtering the filtrate, adding alkali to adjust the pH to 1.5, holding 5 Place the precipitate overnight at ℃, filter and collect the precipitate, dissolve with 80L deionized water by heating and stirring, then add appropriate amount of NaCl and 1% activated carbon, stir at 70-80 ℃ for 1h, filter and take the filtrate, concentrate under reduced pressure to the appropriate concentration, use Adjust the pH to 6.0 with ammonia, incubate at 5°C overnight to precipitate the crystals, filter the crystals, and dry at 105°C to obtain the finished L-isoleucine.
- 9.2 Merck
- 14,5179
- 9.3 BRN
- 1721792
- 9.4 Description
- Crystalline leaflets or a white, crystalline powder having a bitter taste. It is soluble in 25 parts of water, slightly soluble in hot alcohol, and soluble in diluted mineral acids and in alkaline solutions. It sublimes at between 168°C and 170°C, and melts with decomposition at about 284°C. The pH of a 1 in 100 solution is between 5.5 and 7.0.
Absolute: The absolute is prepared by alcoholic extraction of the concrete in approximately 55 to 60% yields. The absolute consists of a semisolid, olive-green mass with a characteristic ambergris odor.
Resinoid and Resin Absolute: The resinoid consists of the hydro carbon extract of the crude resin. The resin absolute consists of the alcoholic extract of the crude labdanum resin. Since this prod uct is a semisolid, nonpourable mass, a high-boiling, odorless solvent may be added prior to evaporation of the alcohol to prepare a pourable liquid.
- 9.5 Chemical Properties
- White crystalline powder
- 9.6 Uses
- L-Isoleucine, also known as Isoleucine, is an amino acid that is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.
L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training.
L-Isoleucine is also classified as a branched-chain amino acid (BCAA). There are three branched-chain amino acids in the body, with the others being L-Valine, and L-Leucine, and all of them help promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue.
- 9.7 Uses
-
L-Isoleucine may be used as a pharmaceutical reference standard for the quantification of the analyte in pharmaceutical formulations using high-performance liquid chromatography technique.
10. Computational chemical data
- Molecular Weight: 131.17292g/mol
- Molecular Formula: C6H13NO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 131.094628657
- Monoisotopic Mass: 131.094628657
- Complexity: 103
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 63.3
- Heavy Atom Count: 9
- Defined Atom Stereocenter Count: 2
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAADSjBgAQCCABAAgAIAACQCAAAAAAAAAAAAIGAAAACABIAgAAAQAAEEAAAAACIAAAKAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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