Basic information Safety Supplier Related

L-Canavanine

Basic information Safety Supplier Related

L-Canavanine Basic information

Product Name:
L-Canavanine
Synonyms:
  • 2-amino-4-(guanidinooxy)butyricacid
  • canavanin
  • canavanine
  • o-((aminoiminomethyl)amino)-l-homoserin
  • o-((aminoiminomethyl)amino)-l-homoserine
  • o-[(aminoiminomethyl)amino]homoserine
  • L-CANAVANINE
  • L-ALPHA-AMINO-GAMMA-[GUANIDINOOXY]-N-BUTYRIC ACID
CAS:
543-38-4
MF:
C5H12N4O3
MW:
176.17
Mol File:
543-38-4.mol
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L-Canavanine Chemical Properties

Melting point:
184°
alpha 
D20 +7.9° (c = 3.2)
Boiling point:
307.78°C (rough estimate)
Density 
1.3685 (rough estimate)
refractive index 
1.7900 (estimate)
storage temp. 
2-8°C
solubility 
H2O: <100 mg/mL
form 
powder
pka
pK1: 2.50(+2);pK2: 6.60(+1);pK3: 9.25(0) (25°C)
PH
7.93
optical activity
+7.920 (H2O)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36
WGK Germany 
3
RTECS 
ES7002000
Hazardous Substances Data
543-38-4(Hazardous Substances Data)

MSDS

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L-Canavanine Usage And Synthesis

Uses

NO synthase inhibitor

Definition

ChEBI: A non-proteinogenicL-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinoge ic.

Biochem/physiol Actions

Canavanine is a naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Overproduction of NO by iNOS plays a crucial role in the pathophysiology of septic shock and chronic inflammation.

Purification Methods

Crystallise S-canavanine from absolute EtOH or aqueous EtOH. [Tomiyama J Biol Chem 111 48 1935 gave pK9.25 (COOH), pK 7.4 (guanidinium), pK 11.5 (NH4+), Gulland & Morris J Chem Soc 763 1935,(±) Frankel et al. J Chem Soc 3127 1963, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2622-2628 1961, Beilstein 4 III 1636, 4 IV 3188.]

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