(2S,3S)-2-amino-3-methylpentanoic acid

• ChemBase ID: 52
• Molecular Formular: C6H13NO2
• Molecular Mass: 131.17292
• Monoisotopic Mass: 131.09462866
• SMILES: OC(=O)[C@@H](N)[C@H](CC)C
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)O)N)C
• 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
• InChIKey: AGPKZVBTJJNPAG-WHFBIAKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-amino-3-methylpentanoic acid
• IUPAC Traditional name: L-isoleucine
• Synonyms: L-(+)-Isoleucine; (2RS,3S)-2-Amino-3-methylpentanoic acid; L-Isoleucine: D-allo-isoleucine; (2S,3S)-2-Amino-3-methylpentanoic acid; (2S,3S)-a-Amino-b-methyl-n-valeric acid; (2S,3S)-a-Amino-b-methylvaleric acid; (S)-Isoleucine; (S,S)-Isoleucine; 2-Amino-3-methylvaleric acid; 2S,3S-Isoleucine; erythro-L-Isoleucine; Isoleucine; L-(+)-Isoleucine; L-Ile; L-Isoleucine; 2-Amino-3-methylpentanoic acid; Isoleucine; L-Isoleucine; H-Ile-OH; (2S,3S)-2-Amino-3-methylpentanoic acid; (2S,3S)-2-氨基-3-甲基戊酸; L-异亮氨酸

Database IDs

• CAS Number: 73-32-5
• EC Number: 200-798-2
• MDL Number: MFCD00064222
• Beilstein Number: 1721792
• Merck Index: 145179
• PubChem SID: 24902116; 24896013; 24896006; 24896115; 160963515; 24881234; 46506864; 24896065
• PubChem CID: 791; 6306
• CHEBI ID: 58045
• Chemspider ID: 6067
• DrugBank ID: DB00167
• KEGG ID: D00065
• Unique Ingredient Identifier: 04Y7590D77
• Wikipedia Title: Isoleucine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.7913082
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.5088165
• LogD (pH = 7.4): -1.5107228
• Log P: -1.5084066
• Molar Refractivity: 34.0939 cm^3
• Polarizability: 13.835553 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.73
• LOG S: -0.06
• Solubility (Water): 1.14e+02 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble1 M at 20 °C, clear, colorless; 1 M HCl: soluble50 mg/mL; 34.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Apperance: powder
• Melting Point: 288 °C (dec.)(lit.); ca 287°C dec.
• Optical Rotation: [α]20/D +38.6 to +42.5°, c = 4 in 6 M HCl; [α]20/D +41.0±1°, c = 5% in 6 M HCl; [α]20/D +41°, c = 4 in 6 M HCl; +40 (c=5 in 5N HCl)
• Absorption Wavelength: λ: 260 nm Amax: 0.07; λ: 280 nm Amax: 0.05
• Hydrophobicity(logP): -1.6

Safety Information

• RTECS: NR4705000
• German water hazard class: 1; 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

Product Information

• Purity: ≥98% (TLC); ≥98.5%; ≥99.0%; ≥99.0% (NT); ≥99.5% (NT); 97%; 98%; 98.5-101.0%; 99%
• Grade: certified reference material; EP; JP; reagent grade; SAJ special grade; TraceCERT®; USP
• Optical Purity: ee: 99% (GLC)
• Packaging: pkg of 1 g
• Suitability: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1% (as SO4); 0.05%
• Impurities: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Ca: ≤50 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤100 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying, 110 °C; 0.05% loss on drying, 20 °C (HV)
• Quality Level: GMP-COMPENDIA
• λ: 1 M in 1 M HCl
• Product Line: BioUltra
• Pharmacopeia Traceability: traceable to PhEur I0460000; traceable to USP 1349502
• Linear Formula: C2H5CH(CH3)CH(NH2)CO2H
• Empirical Formula (Hill Notation): C6H13NO2

DETAILS

DrugBank - DB00167

• Drug Groups: approved; nutraceutical
• Description: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. [PubChem]
• Indication: The branched-chain amino acids may have antihepatic encephalopathy activity in some. They may also have anticatabolic and antitardive dyskinesia activity.
• Pharmacology: They provide ingredients for the manufacturing of other essential biochemical components in the body, some of which are utilized for the production of energy, stimulants to the upper brain and helping you to be more alert.
• Toxicity: Symptoms of hypoglycemia, increased mortality in ALS patients taking large doses of BCAAs
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorbed from the small intestine by a sodium-dependent active-transport process
• External Links: PDRhealth

Sigma Aldrich - I5281

Packaging
Manufactured and Packaged under CGMP

Sigma Aldrich - I2877

Other Notes
Approx. 1:1 mixture of diastereomers
Linkage
Often erroneously called "DL-isoleucine." See separate listing of DL-isoleucine, which is a mixture of 4 stereoisomers.

Sigma Aldrich - I7403

包装
10 mg in autosmp vl

Sigma Aldrich - 58879

Other Notes
Growth requirement of various microorganisms1

Sigma Aldrich - W527602

Packaging
1 kg in poly bottle
100 g in poly bottle

Sigma Aldrich - 56241

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - PHR1099

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Sigma Aldrich - I2752

包装
1 kg in poly bottle
1, 5, 10, 25, 100 g in poly bottle