L-Isovaline Chemical Properties

Melting point:

289.39°C (estimate)

Boiling point:

213.6±23.0 °C(Predicted)

alpha 

D25 +11.13° (c = 5 in H2O)

Density 

1.2000 (estimate)

refractive index 

1.4650 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.38±0.10(Predicted)

form 

Fine Crystalline Powder

color 

White

optical activity

Consistent with structure

InChI

InChI=1S/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m1/s1

InChIKey

GCHPUFAZSONQIV-RXMQYKEDSA-N

SMILES

C(O)(=O)[C@](CC)(C)N

CAS DataBase Reference

595-40-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

TSCA 

No

MSDS

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L-Isovaline Usage And Synthesis

Uses

a-Me-Gly(Ethyl)-OH is used in preparation of peptide compound comprising highly sterically hindered amino acid via reaction of electron-withdrawing group-protected N-unsubstituted-α,α-disubstituted amino acid with peptide followed by N-alkylation.

Synthesis

1.4) Compound F1 (13.8 g, 95.0 mmol) and sodium hydroxide (7.6 g, 190.08 mmol) were added sequentially to a mixture of ethanol (200 mL) and water (1:1 by volume) and heated to reflux for 4 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 7 with 2 M hydrochloric acid solution, followed by evaporation of the solvent. The residue was dissolved in a small amount of water and purified by strongly acidic cation exchange resin 732. The final product G1 (10 g, 90% yield) was obtained as a white solid.

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.]

References

[1] Patent: CN108440320, 2018, A. Location in patent: Paragraph 0033; 0035; 0043

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