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C1625

Sigma-Aldrich

L-Canavanine

≥98% (TLC), powder, from Canavalia ensiformis

Synonym(s):

L-α-Amino-γ-(guanidinooxy)-n-butyric acid

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About This Item

Empirical Formula (Hill Notation):
C5H12N4O3
CAS Number:
543-38-4
Molecular Weight:
176.17
MDL number:
MFCD00055781
UNSPSC Code:
12352209
PubChem Substance ID:
24892427
NACRES:
NA.26

product name

L-Canavanine, ≥98% (TLC), powder, from Canavalia ensiformis

biological source

Canavalia ensiformis

Quality Level

200

assay

≥98% (TLC)

form

powder

color

white to yellow

solubility

H2O: <100 mg/mL

application(s)

detection

storage temp.

2-8°C

SMILES string

N[C@@H](CCONC(N)=N)C(O)=O

InChI

1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1

InChI key

FSBIGDSBMBYOPN-VKHMYHEASA-N

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.
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Nayun Kim et al.
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E Arthur Bell
Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases, 10 Suppl 2, 21-25 (2009-12-16)
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BMC biology, 9, 70-70 (2011-10-26)
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