| Identification | More | [Name]
N-Acetyl-L-valine | [CAS]
96-81-1 | [Synonyms]
ACETYL-L-VALINE
AC-VALINE
AC-VAL-OH
N-ACETYL-L-VALINE
N-ALPHA-ACETYL-L-VALINE
Acetylvaline
L-Valine, N-acetyl-
Valine, N-acetyl-, L-
Ac-L-Val-OH
N-alpha-Actetyl-L-valine
(S)-2-ACETAMIDO-3-METHYLBUTANOIC ACID
N-ACETYL-L-VALINE extrapure for biochemistry | [EINECS(EC#)]
202-537-8 | [Molecular Formula]
C7H13NO3 | [MDL Number]
MFCD00066066 | [Molecular Weight]
159.18 | [MOL File]
96-81-1.mol |
| Chemical Properties | Back Directory | [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. ]
−20°C
| [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
3.62±0.10(Predicted) | [color ]
White | [Optical Rotation]
-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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [HS Code ]
2922498590 |
| Hazard Information | Back Directory | [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ChEBI: An L-valine derivative in which one of the amino hydrogens of L-valine has been replaced by an acetyl group.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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