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L-Azetidine-2-carboxylic acid

Alias: LAzetidine2carboxylic acid; L Azetidine 2 carboxylic acid
Cat No.:V38570 Purity: ≥98%
L-Azetidine-2-carboxylic acid is an endogenously produced metabolite.
L-Azetidine-2-carboxylic acid
L-Azetidine-2-carboxylic acid Chemical Structure CAS No.: 2133-34-8
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
Other Sizes
Official Supplier of:
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Product Description
L-Azetidine-2-carboxylic acid is an endogenously produced metabolite.
Biological Activity I Assay Protocols (From Reference)
Toxicity/Toxicokinetics
Interactions
THE CHRONIC ADMINISTRATION OF CARBON TETRACHLORIDE TO RATS INDUCED CIRRHOSIS AND INCREASED ALBUMIN SYNTHESIS, BUT SIMULTANEOUS ADMIN OF CARBON TETRACHLORIDE WITH L-AZETIDINE-2-CARBOXYLIC ACID DECR ALBUMIN SYNTHESIS AND ELICITED A RETURN OF SERUM ALBUMIN LEVELS TO NORMAL VALUES.
L-AZETIDINE-2-CARBOXYLIC ACID SEVERELY INHIBITED THE INDUCTION OF NITRATE REDUCTASE BY NITRATE IN RADISH AND CAULIFLOWER LEAF TISSUES WITH A LOW L-PROLINE CONTENT. INHIBITION WAS REVERSED BY SIMULTANEOUS INFILTRATION OF L-PROLINE.
Additional Infomation
(S)-azetidine-2-carboxylic acid is the (S)-enantiomer of azetidine-2-carboxylic acid. It is an enantiomer of a (R)-azetidine-2-carboxylic acid.
(S)-Azetidine-2-carboxylic acid has been reported in Convallaria majalis, Clavulinopsis helvola, and other organisms with data available.
See also: Beet (part of).
Mechanism of Action
ALLYLGLYCINE (0.1 MMOL) INHIBITED THE UPTAKE OF 0.1 UMOL 4,5-(3)H-LABELED L-LEUCINE (1 CURIE/MMOLE) AND U-(3)H-LABELED L-PROLINE (266 MCI/MMOLE) BY RAT BRAIN SLICES. LEUCINE UPTAKE WAS NOT LINEAR WITH TIME; PROLINE UPTAKE WAS ALSO INHIBITED BY L-AZETIDINE-2-CARBOXYLIC ACID.
L-AZETIDINE-2-CARBOXYLIC ACID WAS POTENT IN CAUSING AMNESIA OF 1-TRIAL AVOIDANCE CONDITIONING OF THE 2-DAY-OLD CHICK AND IN PREVENTING MECHANICALLY INDUCED SPREADING DEPRESSION IN THE RETINA ISOLATED FROM 2-3 WK-OLD CHICKS. L-AZETIDINE-2-CARBOXYLIC ACID IS INCORPORATED INTO PROTEIN IN PLACE OF L-PROLINE IN SEVERAL PROTEIN-SYNTHESIZING SYSTEMS.
THE ADDITION OF L-AZETIDINE-2-CARBOXYLIC ACID TO THE INCUBATION MEDIUM OF FETAL RAT CALVARIA DECREASED THE INTRACELLULAR FREE PROLINE AND THE RATES OF PROLINE INCORPORATION INTO PROTEIN AND COLLAGEN BY 40-70%. THE ALTERATIONS IN INTRACELLULAR PROLINE CONCN PRODUCED EITHER BY VARYING EXTRACELLULAR PROLINE CONCN OR BY INHIBITING THE UPTAKE OF PROLINE INTO THE INTRACELLULAR POOL MAY CONTRIBUTE TO THE REGULATION OF COLLAGEN SYNTHESIS.
PROLINE PERMEASE FROM PSEUDOMONAS AERUGINOSA OBEYED SATURATION KINETICS & WAS SPECIFIC FOR L-PROLINE. L-AZETIDINE-2-CARBOXYLIC ACID COMPETITIVELY INHIBITED PROLINE UPTAKE. IT WAS ALSO ABLE TO EXCHANGE WITH A PRE-ESTABLISHED LABELED PROLINE INTRACELLULAR POOL.
SIXTEEN-DAY-OLD MOUSE EMBRYONIC ODONTOBLASTS, TREATED FOR 4 DAYS WITH L-2-AZETIDINECARBOXYLIC ACID (50, 100, & 200 GAMMA) WERE POST-MITOTIC, BUT NONPOLARIZED AND DID NOT SECRETE PICROFUCHSIN-POSITIVE SUBSTANCES (COLLAGEN). 18-DAY-OLD EMBRYONIC ODONTOBLASTS TREATED WITH L-2-AZETIDINECARBOXYLIC CONTAINED NO PICROFUCHSIN-POSITIVE SUBSTANCES AND NO COLLAGEN FIBERS OF STRIATION; PREADAMANTOBLASTS WERE POST-MITOTIC BUT NONPOLARIZED.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₄H₇NO₂
Molecular Weight
101.10
Exact Mass
101.047
CAS #
2133-34-8
PubChem CID
16486
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
242.0±33.0 °C at 760 mmHg
Melting Point
206-207 ºC
Flash Point
100.1±25.4 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.499
LogP
-0.83
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
7
Complexity
91.7
Defined Atom Stereocenter Count
1
SMILES
C1CN[C@@H]1C(=O)O
InChi Key
IADUEWIQBXOCDZ-VKHMYHEASA-N
InChi Code
InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
Chemical Name
(2S)-azetidine-2-carboxylic acid
Synonyms
LAzetidine2carboxylic acid; L Azetidine 2 carboxylic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~989.12 mM)
DMSO :< 1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (989.12 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 9.8912 mL 49.4560 mL 98.9120 mL
5 mM 1.9782 mL 9.8912 mL 19.7824 mL
10 mM 0.9891 mL 4.9456 mL 9.8912 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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