| Identification | Back Directory | [Name]
L-Canavanine | [CAS]
543-38-4 | [Synonyms]
AI352153
AI3-52153
AI3 52153
canavanin
canavanine
L-CANAVANINE
FSBIGDSBMBYOPN-VKHMYHEASA-N
(L) Canavanine,(L)Canavanine
(+)-O-(Guanidino)-L-homoserine
2-amino-4-(guanidinooxy)butyricacid
L-CANAVANINE FREE BASE FROM JACK BEA
o-[(aminoiminomethyl)amino]homoserine
o-((aminoiminomethyl)amino)-l-homoserin
BUTYRICACID,2-AMINO-4-(GUANIDINOOXY)-L-
L-Homoserine, O-(aminoiminomethyl)amino-
(S)-2-Amino-4-(guanidinooxy)butyric acid
o-((aminoiminomethyl)amino)-l-homoserine
(S)-2-aMino-4-(guanidinooxy)butanoic acid
l-α-amino-γ-(guanidinooxy)-n-butyric acid
L-canavanine free base from jack beans*crystallin
L-ALPHA-AMINO-GAMMA-[GUANIDINOOXY]-N-BUTYRIC ACID
L-CANAVANINE FREE BASE FROM JACK BEANSCR YSTALLINE
2-amino-4-(diaminomethylideneamino)oxy-butanoic acid
L-Canavanine >=98% (TLC), powder, from Canavalia ensiformis | [Molecular Formula]
C5H12N4O3 | [MDL Number]
MFCD00055781 | [MOL File]
543-38-4.mol | [Molecular Weight]
176.17 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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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| Company Name: |
Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
| Company Name: |
Energy Chemical
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021-58432009 400-005-6266 |
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http://www.energy-chemical.com |
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