| CAS |
2517/4/6 |
| Chinese Name |
L-铃兰氨酸 |
| English Name |
Azetidine-2-carboxylic Acid |
| Synonyms |
;2-氮杂环丁烷甲酸;氮杂环丁烷-2-羧酸;2-Azetidinecarboxylicacid;2-azetidine-carboxylicacid;丁二酸-N，N-二甲基酰肼;N-二甲胺基琥珀酰胺; |
| Molecular Formula |
C4H7NO2 |
| Molecular Weight |
101.1 |
| Solubility |
Soluble in Water |
| Purity |
≥98% |
| Appearance |
White to off-white Solid |
| Storage |
Powder:-20℃，2 years;Insolvent(Mother Liquid):-20℃，6 months;-80℃，1 year |
| EC |
EINECS 219-740-2 |
| MDL |
MFCD00066660 |
| SMILES |
C1CNC1C(=O)O |
| InChIKey |
IADUEWIQBXOCDZ-UHFFFAOYSA-N |
| InChI |
InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7) |
| PubChem CID |
17288 |
| Target Point |
Others |
| Passage |
Others |
| Background |
It is the stereoisomer of S-allyl-l-cysteine, which exists in garlic and has immunomodulatory effects. |
| Biological Activity |
Azetidine-2-carboxylic acid is a non proteinogenic amino acid homologue of proline. Found in common beets. Azetidine-2-carboxylic acid can be misincorporated into proteins in place of proline in many species, including humans. Toxic and teratogenic agent[1][2]. |
| In Vitro |
Administration of azetidine-2-carboxylic acid to growing chick embryos for 5 days produced a marked arrest in the accumulation of collagen and a significant in_x0002_crease in the fragility of the embryos.The effect on collagen in embryos treated with 375 or 500 ~g per day was specific since the decrease in collagen accumulation was consistently over twice the effect on non-collagen proteins. The experiments with cartilage in vitro demonstrated that the principal effect of azetidine-2-carboxylic acid in the first 2 h or so is to increase the intracellular pool of collagen because the collagen containing the analogue cannot be extruded at a normal rate.[3] |
| In Vivo |
Autoradiographs from the embryos labeled in vivo indicated that cells treated with azetidine-2-carboxylic acid for 5 days do not adapt to the repeated exposure to the analogue and they still do not extrude collagen containing the analogue at a normal rate. [3] |
| Animal Experiment |
Azetidine-2-carboxylic acid was dissolved in distilled water and 0.2 ml of solution in the appropriate concentration was applied to the air sack of the chick erabryos daily from day 8 to day 12. Control embryos received 0.2 ml of distilled water daily. [14C] Proline or ~3，4-3H21proline was administered by adding the labeled amino acid to the solution of azetidine-2-carboxylic acid or distilled water which was ad_x0002_ministered to the chick embryos 4-48 h prior to the time the embryos were killed. Femurs and tibiae were removed from the embryo by microscopic dissection.[3] |
| Data Literature Source |
[1]. Rubenstein E，et al. Azetidine-2-carboxylic acid in the food chain. Phytochemistry. 2009 Jan;70(1):100-4.
[2]. Rubenstein E，et al. Misincorporation of the proline analog azetidine-2-carboxylic acid in the pathogenesis of multiple sclerosis: a hypothesis. J Neuropathol Exp Neurol. 2008 Nov;67(11):1035-40.
[3]. Lane JM，et al. Effect of the proline analogue azetidine-2-carboxylic acid on collagen synthesis in vivo. I. Arrest of collagen accumulation in growing chick embryos. Biochim Biophys Acta. 1971 Jun 29;236(3):517-27. |
| Unit |
Bottle |
| Specification |
100mg 250mg 500mg |
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