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

Syntechem Co.,Ltd

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Sigma-Aldrich

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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