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
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
Safety
- Safety Statements
- 22-24/25
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..…
N-Bromosuccinimide Price
- Product number
- 9002357
- Product name
- L-Canaline
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $49
- Updated
- 2024/03/01
- Product number
- 9002357
- Product name
- L-Canaline
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $216
- Updated
- 2024/03/01
- Product number
- 9002357
- Product name
- L-Canaline
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $380
- Updated
- 2024/03/01
- Product number
- 9002357
- Product name
- L-Canaline
- Purity
- ≥95%
- Packaging
- 25mg
- Price
- $830
- Updated
- 2024/03/01
- Product number
- C3827
- Product name
- L-Canaline
- Packaging
- 25mg
- Price
- $947
- Updated
- 2021/12/16
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
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