C1625

Sigma-Aldrich

L-Canavanine

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

Synonym(s):
L-α-Amino-γ-(guanidinooxy)-n-butyric acid
Empirical Formula (Hill Notation):
C5H12N4O3
CAS Number:
Molecular Weight:
176.17
MDL number:
PubChem Substance ID:
NACRES:
NA.26
Pricing and availability is not currently available.

biological source

Canavalia ensiformis

assay

≥98% (TLC)

form

powder

application(s)

detection: suitable

color

white to yellow

solubility

H2O: <100 mg/mL

storage temp.

2-8°C

SMILES string

NC@@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

Related Categories

Packaging

100, 250 mg in poly bottle
1 g in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

20/21/22

Safety Statement

36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis
Certificate of Origin
Bozhena Vynnytska-Myronovska et al.
International journal of cancer, 130(9), 2164-2175 (2011-06-08)
Single amino acid arginine deprivation is a promising strategy in modern metabolic anticancer therapy. Its potency to inhibit tumor growth warrants the search for rational chemo- and radio-therapeutic approaches to be co-applied. In this report, we evaluated, for the first...
Margarita Cabrera et al.
The Journal of biological chemistry, 288(7), 5166-5175 (2012-12-25)
Transport along the endolysosomal system requires multiple fusion events at early and late endosomes. Deletion of several endosomal fusion factors, including the Vac1 tether and the Class C core vacuole/endosome tethering (CORVET) complex-specific subunits Vps3 and Vps8, results in a...
Junjie Tan et al.
Nature communications, 10(1), 439-439 (2019-01-27)
RNA-guided nucleases of the CRISPR/Cas type can be repurposed as programmable nucleotide deaminases to mediate targeted nucleotide substitutions. Such base editors have enormous potential in genome editing, gene therapy and precision breeding. However, current editors suffer from limited specificity in...
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)
Because of the similarity of ALS/PDC symptoms to those of the paralytic disease lathyrism, cycad seeds from Guam were analyzed for the presence of the non-protein amino acid b-ODAP, which is known to cause lathyrism. Although b-ODAP was not detected...
Youngseok Lee et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(4), 1429-1435 (2012-01-27)
Insect survival depends on contact chemosensation to sense and avoid consuming plant-derived insecticides, such as L-canavanine. Members of a family of ∼60 gustatory receptors (GRs) comprise the main peripheral receptors responsible for taste sensation in Drosophila. However, the roles of...

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