N-Acetyl-L-valine Chemical Properties

Melting point:

163-167℃

alpha 

[α]D20 -16～-20゜ (c=5, C2H5OH)

Boiling point:

362.2±25.0 °C(Predicted)

Density 

1.094±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

Crystalline Powder

pka

3.62±0.10(Predicted)

color 

White

optical activity

-18° (C=0.01 g/ml, H2O)

InChI

InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1

InChIKey

IHYJTAOFMMMOPX-LURJTMIESA-N

SMILES

C(O)(=O)[C@H](C(C)C)NC(C)=O

CAS DataBase Reference

96-81-1(CAS DataBase Reference)

NIST Chemistry Reference

L-valine, n-acetyl-(96-81-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

2922498590

MSDS

• Language:English Provider:SigmaAldrich

N-Acetyl-L-valine Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Ac-Val-OH may be employed as a ligand for the meta-selective tert-alkylation reaction.

Definition

ChEBI: An L-valine derivative in which one of the amino hydrogens of L-valine has been replaced by an acetyl group.

General Description

Ac-Val-OH is an N-protected valine amino acid ligand. It participates in the 2,6-diolefination reaction of phenylacetic acids.

Synthesis

The general procedure for the synthesis of N-acetyl-L-valine from L-valine and acetic anhydride was as follows: L-valine (200 g, 1.7 mol) was dissolved in distilled water (500 mL), followed by the addition of 30% sodium hydroxide solution (170 mL). After cooling the reaction mixture to 0-5°C, acetic anhydride (32 mL, 1.4 eq.) was added slowly and dropwise. This was repeated six times (total acetic anhydride: 6 x 32 mL; 30% sodium hydroxide solution: 6 x 34 mL) by alternating dropwise additions of 30% sodium hydroxide solution (34 mL) and acetic anhydride (32 mL) while maintaining the temperature at 0-5°C. After the addition was completed, the reaction mixture continued to be stirred at 0°C for 2 hours. Subsequently, 32% hydrochloric acid (380 mL) was slowly added to adjust the pH to below 3 while maintaining the reaction temperature at 0°C. The resulting slurry was allowed to crystallize for 12 h. The solid product was collected by filtration and the filter cake was washed with 0.1 N hydrochloric acid (100 mL). Finally, the wet N-acetyl-L-valine was dried to give 233 g of white crystalline solid in 86% yield.

IC 50

Human Endogenous Metabolite

References

[1] New Journal of Chemistry, 2002, vol. 26, # 7, p. 834 - 843
[2] Synthetic Communications, 1992, vol. 22, # 2, p. 257 - 264
[3] Patent: WO2005/40097, 2005, A1. Location in patent: Page/Page column 9
[4] Journal of the American Chemical Society, 2011, vol. 133, # 43, p. 17176 - 17179
[5] Journal of the American Chemical Society, 1956, vol. 78, p. 4636,4642

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