L-Canavanine Property

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)

Safety

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

L-Canavanine Chemical Properties,Usage,Production

Uses

NO synthase inhibitor

Definition

ChEBI: L-canavanine is a non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic. It has a role as a phytogenic insecticide and a plant metabolite. It is functionally related to a L-homoserine. It is a conjugate base of a L-canavanine(1+). It is a tautomer of a L-canavanine zwitterion.

Biochem/physiol Actions

L-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.]