L-Azetidine-2-carboxylic acid

Name: L-Azetidine-2-carboxylic acid
Brand: MedChemExpress
SKU: HY-W050044
Rating: 4.5 (1 reviews)

Cat. No.: HY-W050044 Pureza: 99.97%: Ficha de datos
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L-Azetidine-2-carboxylic acid is a proline analog. L-Azetidine-2-carboxylic acid upregulates the lipid autophagy marker LC3-II via activation of the PERK pathway. L-Azetidine-2-carboxylic acid increases pro-apoptotic BAX protein. L-Azetidine-2-carboxylic acid induces ATF6 cleavage and upregulates phosphorylated eIF2α levels. L-Azetidine-2-carboxylic acid induces ER stress, inducing protein misfolding and aggregation. L-Azetidine-2-carboxylic acid shows teratogenic, pro-inflammatory and pro-apoptotic effects.

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L-Azetidine-2-carboxylic acid Estructura química

No. CAS : 2133-34-8

Tamaño	Stock	Cantidad
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in Water ready for reconstitution	En stock	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in Water	En stock	Estimated Time of Arrival: December 31
Solid
100 mg	En stock	Estimated Time of Arrival: December 31
500 mg	En stock	Estimated Time of Arrival: December 31
1 g	En stock	Estimated Time of Arrival: December 31
5 g	Obtener un presupuesto
10 g	Obtener un presupuesto

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Revisión del cliente

Based on 1 publication(s) in Google Scholar

Other Forms of L-Azetidine-2-carboxylic acid:

L-Azetidine-2-carboxylic acid (Standard) Obtener un presupuesto

1 Publications Citing Use of MCE L-Azetidine-2-carboxylic acid

•Mol Cell. 2026 Mar 3:S1097-2765(26)00102-4.

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Ver todos los productos específicos de isoformas Endogenous Metabolite:

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Human Endogenous Metabolite Microbial Metabolite

Ver todos los productos específicos de isoformas Bcl-2 Family:

Ver todas las isoformas

Bcl-2 Bcl-xL Bcl-W Mcl-1 Bfl-1 Bcl-B Bax Bak Bim BNIP3 Bad

Actividad biológica
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Referencias
Revisión del cliente

Descripciòn

IC₅₀ & Target

Human Endogenous Metabolite

In Vitro

L-azetidine-2-carboxylic acid increases glycosylations of collagen in chick-embryo tendon cells^[1].
L-azetidine-2-carboxylic acid (5 mM, 9 h) induces ATF6 cleavage and upregulates BiP expression and phosphorylated eIF2α levels in HeLa cells^[2].
L-azetidine-2-carboxylic acid (1-10 mM) reduces L-[U-14-C]proline incorporation into hemoglobin (25, 58, and 72% for 1, 5, and 10 mM, , respectively) in rabbit reticulocytes^[3].
L-azetidine-2-carboxylic acid (350 μg/egg, daily, 9 days) prevents expression of the chondrogenic phenotype in embryonated eggs of Gallus domesticus^[4].
L-azetidine-2-carboxylic acid (0-2000 µM, 6-24 h) shows pro-inflammatory and pro-apoptotic effects in BV2 microglial cells^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Apoptosis Analysis^[5]

Cell Line:	BV2 cells
Concentration:	1000 µM
Incubation Time:	6, 24 h
Result:	Did not affect Bcl2 protein expression. Increased pro-apoptotic BAX protein both at 6 and 24 h. Increased BAX/Bcl2 ratio after 6 h.

Real Time qPCR^[5]

Cell Line:	BV2 cells
Concentration:	1000 µM
Incubation Time:	6, 24 h
Result:	Induced CD68 after 6 h. Up-regulated MMP-9, but only at 24 h.

In Vivo

L-azetidine-2-carboxylic acid (200-600 mg/kg, i.p., given on gestational days 7-12) exhibits teratogenic effects in hamster fetuses^[6].
L-azetidine-2-carboxylic acid (300 mg/kg, i.p., on day 8 of pregnancy) exhibits teratogenic effects on the skeletal system in rats^[7].
L-azetidine-2-carboxylic acid (300 mg/kg, i.p., single) causes disrupted dentinogenesis in rats and mice^[8].
L-azetidine-2-carboxylic acid (200 mg/kg, twice daily for 2 days) retards lung growth and surfactant synthesis in fetal rats^[9].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Eight-week-old pregnant virgin Wistar rats^[7]
Dosage:	300 mg/kg
Administration:	Intraperitoneal injection (i.p.), on day 8,9, 10,11, 12 or 13 of pregnancy
Result:	Showed skeletal malformations, skeletal variations, delayed ossification and growth retardation. Showed a higher mortality.

Peso molecular

101.10

Fòrmula

C₄H₇NO₂

No. CAS

2133-34-8

Appearance

Solid

Color

White to off-white

SMILES

O=C([C@H]1NCC1)O

Structure Classification

Ketones, Aldehydes, Acids

Initial Source

Endogenous metabolite

Envío

Room temperature in continental US; may vary elsewhere.

Almacenamiento

4°C, protect from light, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

Solvente y solubilidad

In Vitro:

H₂O : 100 mg/mL (989.12 mM; Need ultrasonic)

DMSO : < 1 mg/mL (insoluble or slightly soluble)

Preparing
Stock Solutions

Concentration Solvent Mass	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

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Calculadora de molaridad
Calculadora de dilución

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: PBS
Solubility: 100 mg/mL (989.12 mM); Clear solution; Need ultrasonic

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).

Pureza y Documentación

Purity: 99.97%

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Ficha de datos (281 KB) SDS (394 KB)

COA (250 KB) HNMR (127 KB) RP-HPLC (239 KB)

Instrucciones de manejo (2659 KB)

Referencias

[1]. Oikarinen A, et al. Effect of L-azetidine-2-carboxylic acid on glycosylations of collagen in chick-embryo tendon cells. Biochem J. 1976 Dec 15;160(3):639-45. [Content Brief]

[2]. Roest G, et al. The ER Stress Inducer l-Azetidine-2-Carboxylic Acid Elevates the Levels of Phospho-eIF2α and of LC3-II in a Ca2+-Dependent Manner. Cells. 2018 Nov 30;7(12):239. [Content Brief]

[3]. Baum BJ, et al. Incorporation of L-azetidine-2-carboxylic acid into hemoglobin in rabbit reticulocytes in vitro. J Biol Chem. 1975 Feb 25;250(4):1464-71. [Content Brief]

[4]. Hall BK. Use of the L-proline analog, L-azetidine-2-carboxylic acid (LACA) to analyse embryonic growth and determination and expression of the chondrogenic phenotype in vivo and in vitro. Anat Rec. 1978 Feb;190(2):243-55. [Content Brief]

[5]. Piper JA, et al. Pro-Inflammatory and Pro-Apoptotic Effects of the Non-Protein Amino Acid L-Azetidine-2-Carboxylic Acid in BV2 Microglial Cells. Curr Issues Mol Biol. 2022 Sep 28;44(10):4500-4516. [Content Brief]

[6]. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. [Content Brief]

[7]. NAGAI H, et al. Teratogenic Effect of Proline Analogue L-azetidine-2-carboxylic acid on the Skeletal System in Rats. official journal of Congeital Anomalies Research Association of Japan, 1978, 18(1): 19-23.

[8]. NAGAI H, et al. Disturbance of Dentine Formation in Rats and Mice after Administration of L-azetidine-2-carboxylic acid. official journal of Congeital Anomalies Research Association of Japan, 1978, 18(1): 25-31.

[9]. Adamson IY, et al. L-azetidine-2-carboxylic acid retards lung growth and surfactant synthesis in fetal rats. Lab Invest. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

H₂O	1 mM	9.8912 mL	49.4560 mL	98.9120 mL	247.2799 mL
	5 mM	1.9782 mL	9.8912 mL	19.7824 mL	49.4560 mL
	10 mM	0.9891 mL	4.9456 mL	9.8912 mL	24.7280 mL
	15 mM	0.6594 mL	3.2971 mL	6.5941 mL	16.4853 mL
	20 mM	0.4946 mL	2.4728 mL	4.9456 mL	12.3640 mL
	25 mM	0.3956 mL	1.9782 mL	3.9565 mL	9.8912 mL
	30 mM	0.3297 mL	1.6485 mL	3.2971 mL	8.2427 mL
	40 mM	0.2473 mL	1.2364 mL	2.4728 mL	6.1820 mL
	50 mM	0.1978 mL	0.9891 mL	1.9782 mL	4.9456 mL
	60 mM	0.1649 mL	0.8243 mL	1.6485 mL	4.1213 mL
	80 mM	0.1236 mL	0.6182 mL	1.2364 mL	3.0910 mL
	100 mM	0.0989 mL	0.4946 mL	0.9891 mL	2.4728 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.