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L-Canavanine

Product Name
L-Canavanine
CAS No.
543-38-4
Chemical Name
L-Canavanine
Synonyms
AI352153;canavanin;AI3 52153;AI3-52153;canavanine;L-CANAVANINE;FSBIGDSBMBYOPN-VKHMYHEASA-N;(L) Canavanine,(L)Canavanine;(+)-O-(Guanidino)-L-homoserine;2-amino-4-(guanidinooxy)butyricacid
CBNumber
CB6679318
Molecular Formula
C5H12N4O3
Formula Weight
176.17
MOL File
543-38-4.mol
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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)
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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)
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C1625
Product name
L-Canavanine
Purity
≥98% (TLC), powder, from Canavalia ensiformis
Packaging
100mg
Price
$135
Updated
2024/03/01
Sigma-Aldrich
Product number
C1625
Product name
L-Canavanine
Purity
≥98% (TLC), powder, from Canavalia ensiformis
Packaging
1g
Price
$673
Updated
2024/03/01
Sigma-Aldrich
Product number
C1625
Product name
L-Canavanine
Purity
≥98% (TLC), powder, from Canavalia ensiformis
Packaging
250mg
Price
$179.2
Updated
2024/03/01
Biosynth Carbosynth
Product number
FC162286
Product name
L-Canavanine
Packaging
100mg
Price
$180
Updated
2021/12/16
AK Scientific
Product number
X6876
Product name
L-Canavanine
Packaging
250mg
Price
$255
Updated
2021/12/16
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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.]

L-Canavanine Preparation Products And Raw materials

Raw materials

Preparation Products

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L-Canavanine Suppliers

China 28 Switzerland 1 United Kingdom 1 United States 4 Global 34
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543-38-4, L-CanavanineRelated Search:

JACK BEANS L-Canavanine FMOC-L-CNV(PMC)-OH L-Canavanine sulfate L-CANALINE BASE

  • 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
  • L-CANAVANINE FREE BASE FROM JACK BEANSCR YSTALLINE
  • L-Homoserine, O-(aminoiminomethyl)amino-
  • l-α-amino-γ-(guanidinooxy)-n-butyric acid
  • 2-amino-4-(diaminomethylideneamino)oxy-butanoic acid
  • L-canavanine free base from jack beans*crystallin
  • BUTYRICACID,2-AMINO-4-(GUANIDINOOXY)-L-
  • (+)-O-(Guanidino)-L-homoserine
  • (S)-2-Amino-4-(guanidinooxy)butyric acid
  • (S)-2-aMino-4-(guanidinooxy)butanoic acid
  • L-CANAVANINE FREE BASE FROM JACK BEA
  • FSBIGDSBMBYOPN-VKHMYHEASA-N
  • L-Canavanine >=98% (TLC), powder, from Canavalia ensiformis
  • AI3 52153
  • AI352153
  • AI3-52153
  • (L) Canavanine,(L)Canavanine
  • 543-38-4
  • H2NCNHNHOCH2CH2CHNH2COOH
  • C5H12N4O3
  • BioChemical
  • Biochemicals and Reagents
  • Nitric Oxide Synthase (iNOS)
  • L to O
  • Enzyme Inhibitors
  • Enzyme Inhibitors by Enzyme
  • Enzymes, Inhibitors, and Substrates