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05130

Sigma-Aldrich

L-Alanine

≥99.0% (NT)

Synonym(s):
L-α-Aminopropionic acid, (S)-2-Aminopropionic acid
Empirical Formula (Hill Notation):
C3H7NO2
CAS Number:
Molecular Weight:
89.09
Beilstein:
1720248
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥99.0% (NT)

form

powder or crystals

optical activity

[α]20/D +14.0±1°, c = 5% in 5 M HCl

application(s)

detection: suitable
peptide synthesis: suitable

impurities

≤0.3% foreign amino acids

ign. residue

≤0.1% (as SO4)

loss

≤0.1% loss on drying, 110 °C

color

colorless to white

mp

314.5 °C

solubility

H2O: soluble 89.1 g/l at 20 degrees c
diethyl ether: insoluble
ethanol: soluble (cold 80%)

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤50 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
NH4+: ≤100 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

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

InChI

1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

InChI key

QNAYBMKLOCPYGJ-REOHCLBHSA-N

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Application

L-Alanine is used as a standard to determine absolute concentration of a protein within a mixture of other proteins measured with SI traceability.

Biochem/physiol Actions

Alanine is a nonessential amino acid that plays a key role in the glucose-alanine cycle between muscle tissue and the liver. In amino acid-degrading tissues such as muscle, amino groups are pooled as glutamate by transamination reactions. The amino group of glutamate is transferred to pyruvate via alanine aminotransferase, forming alanine and α-ketoglutarate. The alanine is passed into the blood and transported to the liver. This reaction is reversed in the liver where pyruvate can be used in gluconeogenesis to form glucose, which may return to other tissues through the circulatory system. Increased alanine levels correlate with higher blood pressure, energy intake, cholesterol levels, and body mass index.
L-alanine has the ability to promote the expression of ferritin and antioxidant stress proteins, heme oxygenase-1 (HO-1).

Preparation Note

L-Alanine completely dissolves in water at a concentration of 89.1 g/l at 20°C to yield solution. It is also soluble in 80% ethanol and insoluble in ether.

Other Notes

Preparation of 2-chloropropionic acid; Reduction of derivatives to the aldehyde

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

B. Koppenhoefer et al.
Synthesis, 316-316 (1982)
H. Kogen et al.
Journal of the Chemical Society. Chemical Communications, 311-311 (1987)
Nina Grosser et al.
Biochemical and biophysical research communications, 314(2), 351-355 (2004-01-22)
The amino acid L-alanine has been shown to exert long-term cytoprotection by as yet unidentified molecular mechanisms. Using cultured human endothelial cells (ECV 304), the present study investigates the effect of L-alanine on hydrogen peroxide-mediated cytotoxicity and expression of the...
M. Narita et al.
Tetrahedron Letters, 23, 525-525 (1982)
K. Watanabe et al.
Synthesis, 225-225 (1987)

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