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L-Isoleucine(CAS No. 73-32-5)

L-Isoleucine C6H13NO2 (cas 73-32-5) Molecular Structure

73-32-5 Structure

Identification and Related Records

【Name】
L-Isoleucine
【CAS Registry number】
73-32-5
【Synonyms】
2-Amino-3-methylpentanoic acid, (S-(R*,R*))-
Isoleucine (USP)
(2S,3S)-2-Amino-3-methylpentanoic acid
(2S,3S)-2-amino-3-methyl-pentanoic acid
Isoleucine, L- (8CI)
2-Amino-3-methylvaleric acid
Pentanoic acid, 2-amino-3-methyl-, [S-(R*, R*)]-
(2S,3S)-alpha-Amino-beta-merthyl-n-valeric acid
[S-(R*,R*)]-2-Amino-3-methylpentanoic acid
Pentanoic acid, 2-amino-3-methyl-, (2S,3S)-
2-amino-3-methyl-pentanoic acid
erythro-L-Isoleucine
L-Norvaline, 3-methyl-, erythro-
(2S,3S)-alpha-Amino-beta-methyl-n-valeric acid
Ile
L-Isoleucine (JP14)
Isoleucina [Spanish]
alpha-Amino-beta-methylvaleric acid
Isoleucine (VAN)
Valeric acid, 2-amino-3-methyl-
Isoleucinum [Latin]
7-Isopropoxy-3-Phenyl Chromone
D- Isoleucine
【EINECS(EC#)】
200-798-2
【Molecular Formula】
C6H13NO2 (Products with the same molecular formula)
【Molecular Weight】
131.17
【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-CRCLSJGQSA-N
【Canonical SMILES】
CCC(C)C(C(=O)O)N
【MOL File】
73-32-5.mol

Chemical and Physical Properties

【Appearance】
odorless white solid
【Density】
1.035 g/cm3
【Melting Point】
168-170℃
【Boiling Point】
225.8oCat 760 mmHg
【Refractive Index】
40.5 ° (C=4, 6mol/L HCl)
【Flash Point】
90.3oC
【Alpha】
41 o (C=4, 6N HCL)
【Water】
41.2 g/L (50℃)
【Solubilities】
41.2 g/L (50 oC)
【Color/Form】
Waxy, shiny, rhombic leaflets from alcohol
Crystals
【Stability】
Stable under normal temperatures and pressures.
【HS Code】
29224995
【Storage temp】
Store at RT.
【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)
【Computed Properties】
Molecular Weight:131.17292 [g/mol]
Molecular Formula:C6H13NO2
XLogP3:-1.7
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:3
Exact Mass:131.094629
MonoIsotopic Mass:131.094629
Topological Polar Surface Area:63.3
Heavy Atom Count:9
Formal Charge:0
Complexity:103
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:40

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
R40
【Safety Statements 】
S24/25
【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
【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.
【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
【Octanol/Water Partition Coefficient】
log Kow = -1.72
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Hydrolysis of protein (zein, edestin), amination of alpha-bromo-beta-methylvaleric acid.
U.S. Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 10 thousand - 500 thousand 1990 No Reports 1994 No Reports 1998 No Reports 2002 No Reports
【Usage】

One of the 20 amino acids encoded by our genetic code. An essential amino acid.

Biomedical Effects and Toxicity

【Therapeutic Uses】
Branched chain amino acid (BCAA)-enriched protein or amino acid mixtures and, in some cases, BCAA alone, have been used in the treatment of a variety of metabolic disorders. These amino acids have received considerable attention in efforts to reduce brain uptake of aromatic amino acids and to raise low circulating levels of BCAA in patients with chronic liver disease and encephalopathy. They have also been used in parenteral nutrition of patients with sepsis and other abnormalities.
/Experimental Therapy/ Upper gastrointestinal (GI) bleeding in cirrhotic patients has a high incidence of mortality and morbidity. Postbleeding catabolism has been hypothesized to be partly due to the low biological value of hemoglobin, which lacks the essential amino acid isoleucine. The aims were to study the metabolic consequences of a "simulated" upper GI bleed in patients with cirrhosis of the liver and the effects of intravenous infusion of isoleucine. Portal drained viscera, liver, muscle, and kidney protein kinetics were quantified using a multicatheterization technique during routine portography. Sixteen overnight-fasted, metabolically stable patients who received an intragastric infusion of an amino acid solution mimicking hemoglobin every 4 hours were randomized to saline or isoleucine infusion and received a mixture of stable isotopes (L-[ring-2H5]phenylalanine, L-[ring-2H4]tyrosine, and L-[ring-2H2]tyrosine) to determine organ protein kinetics. This simulated bleed resulted in hypoisoleucinemia that was attenuated by isoleucine infusion. Isoleucine infusion during the bleed resulted in a positive net balance of phenylalanine across liver and muscle, whereas renal and portal drained viscera protein kinetics were unaffected. In the control group, no significant effect was shown...
【Biomedical Effects and Toxicity】
Although the free amino acids dissolved in the body fluids are only a very small proportion of the body's total mass of amino acids, they are very important for the nutritional and metabolic control of the body's proteins. ... Although the plasma compartment is most easily sampled, the concentration of most amino acids is higher in tissue intracellular pools. Typically, large neutral amino acids, such as leucine and phenylalanine, are essentially in equilibrium with the plasma. Others, notably glutamine, glutamic acid, and glycine, are 10- to 50-fold more concentrated in the intracellular pool. Dietary variations or pathological conditions can result in substantial changes in the concentrations of the individual free amino acids in both the plasma and tissue pools. /Amino acids/
After ingestion, proteins are denatured by the acid in the stomach, where they are also cleaved into smaller peptides by the enzyme pepsin, which is activated by the increase in stomach acidity that occurs on feeding. The proteins and peptides then pass into the small intestine, where the peptide bonds are hydrolyzed by a variety of enzymes. These bond-specific enzymes originate in the pancreas and include trypsin, chymotrypsins, elastase, and carboxypeptidases. The resultant mixture of free amino acids and small peptides is then transported into the mucosal cells by a number of carrier systems for specific amino acids and for di- and tri-peptides, each specific for a limited range of peptide substrates. After intracellular hydrolysis of the absorbed peptides, the free amino acids are then secreted into the portal blood by other specific carrier systems in the mucosal cell or are further metabolized within the cell itself. Absorbed amino acids pass into the liver, where a portion of the amino acids are taken up and used; the remainder pass through into the systemic circulation and are utilized by the peripheral tissues. /Amino acids/
The intraerythrocytic malaria parasite derives much of its requirement for amino acids from the digestion of the hemoglobin of its host cell. However, one amino acid, isoleucine, is absent from adult human hemoglobin and must therefore be obtained from the extracellular medium. ... The mechanisms involved in the uptake of isoleucine by the intraerythrocytic parasite /are characterized/. Under physiologic conditions the rate of transport of isoleucine into human erythrocytes infected with mature trophozoite-stage Plasmodium falciparum parasites is increased to approximately 5-fold that in uninfected cells, with the increased flux being via the new permeability pathways (NPPs) induced by the parasite in the host cell membrane. Transport via the NPPs ensures that protein synthesis is not rate limited by the flux of isoleucine across the erythrocyte membrane. On entering the infected erythrocyte, isoleucine is taken up into the parasite via a saturable, ATP-, Na+-, and H+-independent system which has the capacity to mediate the influx of isoleucine in exchange for leucine (liberated from hemoglobin). The accumulation of radiolabeled isoleucine within the parasite is mediated by a second (high-affinity, ATP-dependent) mechanism, perhaps involving metabolism and/or the concentration of isoleucine within an intracellular organelle.

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