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L-CANALINE BASE

Product Name
L-CANALINE BASE
CAS No.
496-93-5
Chemical Name
L-CANALINE BASE
Synonyms
Canalin;canaline;L-Canalin;L-CANALINE BASE;O-AMINO-L-HOMOSERINE;L-Canaline L-Canaline;L-Homoserine, O-amino-;L-CANALINE BASE USP/EP/BP;DL-Carnitine DL-Carnitine;2-Amino-4-(aminooxy)butyric acid
CBNumber
CB8497967
Molecular Formula
C4H10N2O3
Formula Weight
134.13
MOL File
496-93-5.mol
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L-CANALINE BASE Property

Density 
1.298
storage temp. 
2-8°C
solubility 
≤1mg/ml in DMSO
form 
crystalline solid
pka
pK1: 2.40;pK2: 3.70;pK3: 9.20 (25°C)
color 
White to off-white
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Safety

Safety Statements 
22-24/25
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H318Causes serious eye damage

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
9002357
Product name
L-Canaline
Purity
≥95%
Packaging
1mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
9002357
Product name
L-Canaline
Purity
≥95%
Packaging
5mg
Price
$216
Updated
2024/03/01
Cayman Chemical
Product number
9002357
Product name
L-Canaline
Purity
≥95%
Packaging
10mg
Price
$380
Updated
2024/03/01
Cayman Chemical
Product number
9002357
Product name
L-Canaline
Purity
≥95%
Packaging
25mg
Price
$830
Updated
2024/03/01
ApexBio Technology
Product number
C3827
Product name
L-Canaline
Packaging
25mg
Price
$947
Updated
2021/12/16
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L-CANALINE BASE Chemical Properties,Usage,Production

Description

L-Canaline is an aminooxy analog of ornithine that irreversibly inhibits aminotransferases (transaminases), including ornithine aminotransferase (Ki = 2 μM). It forms oximes with α-keto acids and aldehydes, most notably with pyridoxal phosphate, an essential cofactor of aminotransferases. L-Canaline is naturally found in plants, including legumes, and is involved in the metabolism of L-canavanine, an aminooxy analog of arginine. It is cytotoxic to a range of organisms, including bacteria, insects, and parasites.

Definition

ChEBI: L-canaline is a non-proteinogenic L-alpha-amino acid that is L-homoserine in which the hydroxy group at position 4 is substituted by an aminooxy group. It has been isolated from legumes and plays an essential role in lugume chemical defense against insects. It has a role as a plant metabolite, an antineoplastic agent, an antimetabolite and a phytogenic insecticide. It is functionally related to a L-homoserine. It is a tautomer of a L-canaline zwitterion.

Synthesis Reference(s)

Tetrahedron, 23, p. 4441, 1967 DOI: 10.1016/S0040-4020(01)88842-6

in vitro

canaline strongly inhibited the activity of pyridoxal-dependent enzymes, including amino acid decarboxylases, 5-hydroxytryptophan decarboxylase, aminotransferases, tyrosine aminotransferase, ornithine transcarbamylase and plasma diamino-oxidase. the canaline inhibition was due to complex formation between canaline and the pyridoxal coenzyme. l-canaline is one of the most potent inhibitors of pyridoxal enzymes. the ic50 value of l-canaline against ornithine aminotransferase was 3 ×10-6m [4].

in vivo

intraperitoneal administration of 500 mg of dl-canaline/kg body wt. only produced a transient inhibition of oat in brain and liver by 65-70%, suggesting that dl-canaline was not a useful tool in studies of biological consequences of oat inhibition. [1].

References

[1] bolkenius f n, kndgen b, seiler n. dl-canaline and 5-fluoromethylornithine. comparison of two inactivators of ornithine aminotransferase[j]. biochemical journal, 1990, 268(2): 409-414.
[2] rosenthal g a, rhodes d. l-canavanine transport and utilization in developing jack bean, canavalia ensiformis (l.) dc.[leguminosae][j]. plant physiology, 1984, 76(2): 541-544.
[3] peraino c, bunville l g, tahmisian t n. chemical, physical, and morphological properties of ornithine aminotransferase from rat liver[j]. journal of biological chemistry, 1969, 244(9): 2241-2249.
[4] rahiala e l, kekomki m, jnne j, et al. inhibition of pyridoxal enzymes by l-canaline[j]. biochimica et biophysica acta (bba)-enzymology, 1971, 227(2): 337-343.

L-CANALINE BASE Preparation Products And Raw materials

Raw materials

Preparation Products

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L-CANALINE BASE Suppliers

China 30 Germany 2 Switzerland 1 United States 12 Global 45
TargetMol Chemicals Inc.
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Alchem Pharmtech,Inc.
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TargetMol Chemicals Inc.
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ApexBio Technology
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Cayman Chemical Company
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Riedel-de Haen AG
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496-93-5, L-CANALINE BASERelated Search:

Phenol 2,4,6-Tribromophenol Sodium 2-hydroxybenzenesulfonate L-Canavanine Z-ASP(OSU)-OME FMOC-L-CAN(BOC)-OH (S)-HEXYLHIBO FMOC-L-CNV(PMC)-OH Z-ASP(OSU)-OBZL L-Canavanine sulfate BOC-ASP(OSU)-OBZL L-CANALINE BASE

  • (2S)-4-aminooxy-2-ammoniobutanoate
  • L-CANALINE BASE
  • canaline
  • O-AMINO-L-HOMOSERINE
  • Canalin
  • L-Canalin
  • 2-Amino-4-(aminooxy)butyric acid
  • (2S)-2-amino-4-aminooxybutanoic acid
  • (2S)-2-amino-4-aminooxy-butyric acid
  • (2S)-2-azanyl-4-azanyloxy-butanoic acid
  • DL-Carnitine DL-Carnitine
  • L-Canaline L-Canaline
  • (S)-2-Amino-4-(aminooxy)butanoic acid
  • L-α-Amino-γ-(aminooxy)-n-butyric acid
  • L-Homoserine, O-amino-
  • (2S)-2-amino-4-aminooxybutanoicaci
  • L-CANALINE BASE USP/EP/BP
  • 496-93-5
  • Amino Acids