31138-12-2

Basic information

• Product Name: 4-Methylene-L-glutamine
• Synonyms: 4-Methylene-L-glutamine;γ-Methylene-L-glutamine
• CAS NO: 31138-12-2
• Molecular Formula: C₆H₁₀N₂O₃
• Molecular Weight: 158.16
• Mol File: 31138-12-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 171-173 °C (decomp)
• Boiling Point: 452.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.296±0.06 g/cm3(Predicted)
• PKA: 2.14±0.10(Predicted)
• CAS DataBase Reference: 4-Methylene-L-glutamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylene-L-glutamine(31138-12-2)
• EPA Substance Registry System: 4-Methylene-L-glutamine(31138-12-2)

Safety Data

• Hazardous Substances Data: 31138-12-2(Hazardous Substances Data)

Usage

General Description

4-Methylene-L-glutamine, also known as Citrulline, is an important amino acid that occurs naturally in the human body. It plays a key role in several physiological processes, including the production of nitric oxide, a molecule that improves blood flow and promotes cardiovascular health. It is often used in dietary supplements and sports performance enhancement products as it can improve exercise performance and recovery by increasing blood flow to muscles. It can also aid in detoxifying the body by helping to remove ammonia, a toxic byproduct of metabolism. Despite being produced naturally in the body, it can also be obtained from certain foods like watermelon and through supplementation.

Relevant articles and documents

An efficient synthetic route tol-γ-methyleneglutamine and its amide derivatives, and their selective anticancer activity

In cancer cells, glutaminolysis is the primary source of biosynthetic precursors, fueling the TCA cycle with glutamine-derived α-ketoglutarate. The enhanced production of α-ketoglutarate is critical to cancer cells as it provides carbons for the TCA cycle to produce glutathione, fatty acids, and nucleotides, and contributes nitrogens to produce hexosamines, nucleotides, and many nonessential amino acids. Efforts to inhibit glutamine metabolism in cancer using amino acid analogs have been extensive.l-γ-Methyleneglutamine was shown to be of considerable biochemical importance, playing a major role in nitrogen transport inArachisandAmorphaplants. Herein we report for the first time an efficient synthetic route tol-γ-methyleneglutamine and its amide derivatives. Many of thesel-γ-methyleneglutamic acid amides were shown to be as efficacious as tamoxifen or olaparib at arresting cell growth among MCF-7 (ER+/PR+/HER2?), and SK-BR-3 (ER?/PR?/HER2+) breast cancer cells at 24 or 72 h of treatment. Several of these compounds exerted similar efficacy to olaparib at arresting cell growth among triple-negative MDA-MB-231 breast cancer cells by 72 h of treatment. None of the compounds inhibited cell growth in benign MCF-10A breast cells. Overall,N-phenyl amides andN-benzyl amides, such as3,5,9, and10, arrested the growth of all three (MCF-7, SK-BR-3, and MDA-MB-231) cell lines for 72 h and were devoid of cytotoxicity on MCF-10A control cells;N-benzyl amides with an electron withdrawing group at theparaposition, such as5and6, inhibited the growth of triple-negative MDA-MB-231 cells commensurate to olaparib. These compounds hold promise as novel therapeutics for the treatment of multiple breast cancer subtypes.