595-40-4

Basic information

• Product Name: L-Isovaline
• Synonyms: 2,3-Dimethylalanine;2-azanyl-2-methyl-butanoic acid;L(+)-Isovaline Monohydrate, (>99% ee), 99+% 250MG;L(+)-Isovaline Monohydrate;α-Me-Gly(Ethyl)-OH·H2O;(R)-2-AMINO-2-METHYLBUTYRIC ACID;(S)-2-Amino-2-Methylbutanoic Acid;(S)-(+)-2-Amino-2-methylbutanoicacidmonohydrate(e.e.)
• CAS NO: 595-40-4
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.15
• Product Categories: Amino Acid Derivatives;Valine [Val, V];unnatural amino acids;α-Methyl Amino Acids;pharmacetical
• Mol File: 595-40-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 289.39°C (estimate)
• Boiling Point: 213.641 °C at 760 mmHg
• Flash Point: 83.008 °C
• Appearance: White/Fine Crystalline Powder
• Density: 1.2000 (estimate)
• Vapor Pressure: 0.0633mmHg at 25°C
• Refractive Index: 1.4650 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.38±0.10(Predicted)
• CAS DataBase Reference: L-Isovaline(CAS DataBase Reference)
• NIST Chemistry Reference: L-Isovaline(595-40-4)
• EPA Substance Registry System: L-Isovaline(595-40-4)

Safety Data

• Safety Statements: 24/25
• TSCA: No
• Hazardous Substances Data: 595-40-4(Hazardous Substances Data)

Usage

Purification Methods

Crystallise it from aqueous Me2CO, or better by dissolving in H2O and adding excess Me2CO. [Baker et al. J Am Chem Soc 74 4701 1952, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2573-2577 1961.]

InChI:InChI=1/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m0/s1

Upstream product

• 29588-10-1 (+/-)-2-formylamino-2-methyl-butyric acid 
• 58279-59-7 N-chloroacetyl-DL-isovaline 
• 1266681-11-1 (3S,5aR,6aS,7aS)-3-ethyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 59209-90-4 (RS)-2-amino-2-methylbutanamide 
• 4475-95-0 2-amino-2-methylbutanenitrile 
• 13893-46-4 ethyl (R)-2-amino-2-methylbutyrate 
• 1204593-74-7 (3S,6S)-1,4-N,N-[(S)-phenylethyl]-3,6-diethyl-3,6-dimethylpiperazine-2,5-dione 
• 595-39-1 DL-isovaline 
• 123463-75-2 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen ethyl(methyl)malonate 
• 295799-94-9 (3S,6R)-N-1-(tert-butoxycarbonyl)-3-ethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone 
• 123463-88-7 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'-amino-2'-methylbutanoate 
• 29588-12-3 N-formyl-L-isovaline 

Downstream Products

• 3739-30-8 2-hydroxy-2-methylbutyric acid 
• 92760-72-0 L-isovalin methyl ester hydrochloride 
• 160171-18-6 (+)-S-zoxamide 
• 208262-74-2 C₁₃H₁₆FNO₃ 
• 1177452-06-0 Z-L-Iva-Aib-OtBu 
• 1177452-09-3 Z-L-Leu-L-Iva-Aib-OtBu 
• 328402-29-5 Z-L-Iva-L-ATANP(Boc)2-(L-Iva)2-OMe 
• 328402-27-3 Z-L-ATANP(Boc)2-(L-Iva)2-OMe 

Relevant articles and documents

Amino Acid-Derived trans-N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility

N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by "self-regeneration of stereochemistry" methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presence of pyridine may be made fully diastereoselective for the trans-N-chloroformylimidazolidinones, and we detail the conformational features of the products. We show that despite the presence of the electrophilic carbamoyl chloride function the products show remarkable stability and may be deprotonated to form enolates with useful reactivity for the synthesis of amino acid derivatives.

Synthesis and conformational analysis of efrapeptins

The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidumare inhibitors of F1-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in Cα- dialkyl amino acids (Aib, Iva, Acc) and contain one β-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogues of efrapeptin C were synthesized using α-azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F1-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 310-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 310-helical conformation. Copyright

(S)-α-methyl,α-amino acids: A new stereocontrolled synthesis

A new and convenient stereocontrolled synthesis of the optically pure (S)-α-methyl,α-amino acids 6(a-d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.