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
- Molecular Weight:
- 134.13
- MDL Number:
- MFCD00057642
- MOL File:
- 496-93-5.mol
| 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) |
| FDA UNII | T7H2XP1ZNS |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS05 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H332-H302-H312-H335-H315-H318 | |||||||||
| Precautionary statements | P261-P271-P304+P340-P312-P280-P305+P351+P338-P310-P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P264-P280-P302+P352-P321-P332+P313-P362 | |||||||||
| Safety Statements | 22-24/25 | |||||||||
| NFPA 704 |
|
L-CANALINE BASE price More Price(17)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 9002357 | L-Canaline ≥95% | 496-93-5 | 1mg | $49 | 2024-03-01 | Buy |
| Cayman Chemical | 9002357 | L-Canaline ≥95% | 496-93-5 | 5mg | $216 | 2024-03-01 | Buy |
| Cayman Chemical | 9002357 | L-Canaline ≥95% | 496-93-5 | 10mg | $380 | 2024-03-01 | Buy |
| Cayman Chemical | 9002357 | L-Canaline ≥95% | 496-93-5 | 25mg | $830 | 2024-03-01 | Buy |
| ApexBio Technology | C3827 | L-Canaline | 496-93-5 | 25mg | $947 | 2021-12-16 | Buy |
L-CANALINE BASE Chemical Properties,Uses,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
L-CANALINE BASE Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22968 | 58 |
| Alchem Pharmtech,Inc. | 8485655694 | sales@alchempharmtech.com | United States | 63711 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49391 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | 1026@dideu.com | China | 27486 | 58 |
| LEAP CHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 24738 | 58 |
| LEAPCHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 43348 | 58 |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131980 | 58 |
| DONBOO AMINO ACID COMPANY | +8613063595538 | donboo@donboo.com | China | 9365 | 58 |
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42982 | 64 |