l-canaline base

Modify Date: 2024-01-17 09:49:46

l-canaline base Structure
l-canaline base structure
 Common Name l-canaline base
CAS Number 496-93-5 Molecular Weight 134.13400
Density 1.298g/cm3 Boiling Point 378.1ºC at 760mmHg
Molecular Formula C4H10N2O3 Melting Point N/A
MSDS N/A Flash Point 182.5ºC

 Use of l-canaline base


L-Canaline is a nonprotein amino acid stored in many leguminous plants. L-Canaline is a cytotoxic metabolite catalyzed by L-canavanine and its arginase. L-Canaline is a potent and irreversible inhibitor of ornithine aminotransferase. L-Canaline inhibits the growth of the malaria parasite Plasmodium falciparum with an IC50 of 297 nM. L-Canaline has anticancer and antiproliferative effects[1][2][3].

 Names

Name (2S)-2-amino-4-aminooxybutanoic acid
Synonym More Synonyms

 l-canaline base Biological Activity

Description L-Canaline is a nonprotein amino acid stored in many leguminous plants. L-Canaline is a cytotoxic metabolite catalyzed by L-canavanine and its arginase. L-Canaline is a potent and irreversible inhibitor of ornithine aminotransferase. L-Canaline inhibits the growth of the malaria parasite Plasmodium falciparum with an IC50 of 297 nM. L-Canaline has anticancer and antiproliferative effects[1][2][3].
Related Catalog
Target

IC50: 297 nM (Plasmodium falciparum)[3]; Ornithine aminotransferase[1]
In Vitro L-Canaline treatment inhibits the proliferation of PBMCs after stimulation by phorbol 12-myristate-13-acetate (PMA) or via the mixed lymphocyte reaction. The greatest effect is seen with PMA-stimulated cells, where L-canaline has an IC50 of 0.26 mM. L-Canaline is slightly less toxic to PBMCs stimulated via the mixed lymphocyte reaction (IC50 of 0.54 mM)[1].L-canaline inhibits L-lysine flux competitively (Ki of 4.6 mM) in astrocytes and astrocytoma cells[2].
In Vivo L-Canaline decreases the aspartic acid content of tissues of the medulla oblongata of male Wistar rats, but it does not affect the evoked release of this nonprotein amino acid into these tissues[2]. Intraseptal injection of 100 μg of L-canaline into male Sprague-Dawley rats causes a 90% decrease in the omithine aminotransferase activity of the septum tissues evaluated from animals killed 1 h later[2].
References

[1]. Bence AK, et al. The antiproliferative and immunotoxic effects of L-canavanine and L-canaline. Anticancer Drugs. 2002 Mar;13(3):313-20.

[2]. Rosenthal GA. L-canaline: a potent antimetabolite and anti-cancer agent from leguminous plants. Life Sci. 1997;60(19):1635-41.

[3]. Berger BJ. Antimalarial activities of aminooxy compounds. Antimicrob Agents Chemother. 2000 Sep;44(9):2540-2.

 Chemical & Physical Properties

Density 1.298g/cm3
Boiling Point 378.1ºC at 760mmHg
Molecular Formula C4H10N2O3
Molecular Weight 134.13400
Flash Point 182.5ºC
Exact Mass 134.06900
PSA 98.57000
LogP 0.07930
Vapour Pressure 9.22E-07mmHg at 25°C
Index of Refraction 1.51

 Safety Information

Hazard Codes Xi
Safety Phrases S22-S24/25
HS Code 2922509090

 Synthetic Route

ethyl N-[2-(2,5-dioxoimidazolidin-4-yl)ethoxy]carbamate structure

ethyl N-[2-(2,5...

CAS#:92117-88-9

~%

l-canaline base Structure

l-canaline base

CAS#:496-93-5
Literature: Nyberg; Christensen Journal of the American Chemical Society, 1957 , vol. 79, p. 1222,1225
Nα-Benzoyl-Nγ-diphenylmethylen-DL-canalin, α-Benzoylamino-γ-(diphenyl-methylenaminooxy)]-buttersaeure structure

Nα-Benzoyl-Nγ-d...

CAS#:15985-58-7

~%

l-canaline base Structure

l-canaline base

CAS#:496-93-5
Literature: Gilon,C. et al. Tetrahedron, 1967 , vol. 23, p. 4441 - 4447
N/A structure

N/A

CAS#:101794-06-3

~%

l-canaline base Structure

l-canaline base

CAS#:496-93-5
Literature: Knobler; Frankel Journal of the Chemical Society, 1958 , p. 1629
DL-CYCLOHOMOSERINE structure

DL-CYCLOHOMOSERINE

CAS#:1192-69-4

~%

l-canaline base Structure

l-canaline base

CAS#:496-93-5
Literature: SCHEBO.BIOTECH AG Patent: WO2005/54174 A2, 2005 ; Location in patent: Page/Page column 17-18 ;

 Customs

HS Code 2922509090
Summary 2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Synonyms

L-2-amino-4-(aminooxy)butyric acid
O-Amino-homoserin
Canaline
O-amino-homoserine
O-amino-DL-homoserine
O-Amino-DL-homoserin
2-amino-4-aminooxybutanoic acid
L-a-amino-g-(aminooxy)-n-butyric acid
(S)-2-Amino-4-(aminooxy)butanoic acid
L-2-amino-4-(aminooxy)butyrate
L-Homoserine,O-amino
O-Amino-L-homoserine
L-Canaline
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