ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Leucine derivatives N-Acetyl-L-leucine

N-Acetyl-L-leucine

Product NameN-Acetyl-L-leucine
CAS1188-21-2
MFC8H15NO3
MW173.21
EINECS214-706-3
MOL File1188-21-2.mol

Chemical Properties

Melting point	187-190 °C(lit.)
alpha	-24.5 º (c=4, MeOH)
Boiling point	303.86°C (rough estimate)
Density	1.1599 (rough estimate)
refractive index	-22 ° (C=5, EtOH)
storage temp.	Sealed in dry,Room Temperature
solubility	DMSO (Slightly), Ethanol (Slightly), Water (Slightly, Heated)
pka	3.67±0.10(Predicted)
form	Crystalline Powder
color	White
optical activity	[α]25/D 23±3°, c = 2 in ethanol
Water Solubility	0.81 g/100 mL (20 ºC)
BRN	1724849
Major Application	peptide synthesis
InChI	1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t7-/m0/s1
InChIKey	WXNXCEHXYPACJF-ZETCQYMHSA-N
SMILES	CC(C)C[C@H](NC(C)=O)C(O)=O
CAS DataBase Reference	1188-21-2(CAS DataBase Reference)
NIST Chemistry Reference	L-leucine, n-acetyl-(1188-21-2)
EPA Substance Registry System	L-Leucine, N-acetyl- (1188-21-2)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	24/25-36-26
WGK Germany	3
TSCA	TSCA listed
HazardClass	IRRITANT
HS Code	29241900
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

N-Acetyl-L-(-)-leucine is used in the preparation of small molecule inhibitors of anti-apoptotic Bcl-2 family proteins. Also used in the preparation of amphiphilic copolymers involving hydrophobic amino acid and oligopeptide side chains for optical tumor imaging in vivo.

Definition

ChEBI: The N-acetyl derivative of L-leucine.

reaction suitability

reaction type: C-H Activation
reaction type: solution phase peptide synthesis
reagent type: catalyst
reaction type: Peptide Synthesis

in vivo

Levacetylleucine (60 mg/kg, i.v., administration on days 1, 2 and 3 for 15 days) decreases the postural imbalance scores and accelerates the course of postural compensation induced by UL in rats^[3].
Levacetylleucine (100 mg/kg, oral gavage, administration daily for 28 days) attenuates cortical cell death afer traumatic brain injury (TBI) in N-Acetyl-L-leucine-treated TBI mouse cortices^[4].

Animal Model:	Male Sprague-Dawley rats (mean 400±20 g, age 3 months) after chemical UL^[3]
Dosage:	60 mg/kg
Administration:	i.v., 15 days
Result:	Significantly decreased the postural imbalance scores on 7 day and accelerated the course of postural compensation by about 6 days in rats.

Animal Model:	C57/BL6 mice^[4]
Dosage:	100 mg/kg
Administration:	oral gavage, administration daily for 1-28 days
Result:	Did not afect food intake and body weight in mice.

Animal Model:	N-Acetyl-L-leucine-treated TBI mouse cortices^[4]
Dosage:	100 mg/kg
Administration:	oral gavage, administration daily for 28 days
Result:	Prevented cortical cell death which peaks at early time points (day 1) afer TBI in N-Acetyl-L-leucine-treated TBI mouse cortices.

IC 50

Human Endogenous Metabolite

Preparation Products And Raw materials