2-C-Methyl-D-ribono-1,4-lactone: properties, applications and safety

General Description

2-C-Methyl-D-ribono-1,4-lactone is a compound with a molecular weight of 162.14 g/mol and specific molecular characteristics, including a topological polar surface area of 87Ų and three hydrogen bond donors. It exhibits moderate hydrophobicity with a XLogP3-AA value of -1.2 and has predicted properties such as a melting point range of 150-160°C, a boiling point of 338.3±11.0°C, and a density of 1.512±0.06 g/cm3. It is recommended to be stored sealed in a dry environment at temperatures below -20°C. This compound is valuable for applications in organic synthesis, enabling the synthesis of enantiomerically pure 4-substituted riboses and the preparation of saccharinic acids, lactones, herbicidal esters, and branched nucleosides. Safety data indicate that it is not classified as hazardous and does not carry specific GHS label elements or hazard statements, posing minimal risks when handled and stored properly. Overall, 2-C-Methyl-D-ribono-1,4-lactone's unique properties make it a versatile and valuable compound for pharmaceuticals, organic synthesis, and biochemical research.

Figure 1. 2-C-Methyl-D-ribono-1,4-lactone

Properties

2-C-Methyl-D-ribono-1,4-lactone is a compound with the chemical formula C6H10O5 and a molecular weight of 162.14 g/mol. It possesses distinct molecular characteristics, including a topological polar surface area of 87Ų and a complexity of 180. This compound has three hydrogen bond donors, five hydrogen bond acceptors, one rotatable bond, and 11 heavy atoms, indicating its potential for interactions with other molecules. In terms of solubility, 2-C-Methyl-D-ribono-1,4-lactone displays moderate hydrophobicity with a XLogP3-AA value of -1.2, resulting in slight solubility in DMSO, methanol, and water. It is a solid with a white to off-white color and predicted properties such as a melting point range of 150-160°C, a boiling point of 338.3±11.0°C, and a density of 1.512±0.06 g/cm3. To preserve its integrity, it is recommended to store this compound sealed in a dry environment, preferably in a freezer at temperatures below -20°C. These unique properties make 2-C-Methyl-D-ribono-1,4-lactone a valuable compound for various applications in pharmaceuticals, organic synthesis, and biochemical research due to its potential for molecular interactions and specific solubility characteristics. ¹

Applications

2-C-Methyl-D-ribono-1,4-lactone is a compound that finds various applications in organic synthesis. Its primary use lies in the synthesis of enantiomerically pure 4-substituted riboses. By utilizing this lactone, chemists can introduce specific substituents at the 4-position of ribose molecules, allowing for the creation of diverse ribose derivatives with desired stereochemistry. Furthermore, 2-C-Methyl-D-ribono-1,4-lactone plays a vital role in the preparation of saccharinic acids and lactones through a chemical transformation known as the Amadori rearrangement. This rearrangement reaction enables the conversion of reducing sugars, such as the lactone, into valuable synthetic intermediates. These saccharinic acids and lactones serve as building blocks or synthons for the synthesis of various compounds, including herbicidal esters and branched nucleosides. The herbicidal esters derived from the lactone-based synthesis possess potent weed-killing properties, making them valuable in agricultural applications. Additionally, the lactone's involvement in the synthesis of branched nucleosides expands its utility in the field of medicinal chemistry. In summary, 2-C-Methyl-D-ribono-1,4-lactone serves as a versatile compound in organic synthesis. Its applications range from the synthesis of enantiomerically pure ribose derivatives to the preparation of saccharinic acids, lactones, herbicidal esters, and branched nucleosides. These diverse applications highlight the significance of this lactone in various scientific disciplines. ²

Safety

2-C-Methyl-D-ribono-1,4-lactone is commonly used in industrial and scientific research applications. It is characterized by its chemical properties and safety considerations, as outlined in the Safety Data Sheets. According to the SDS, 2-C-Methyl-D-ribono-1,4-lactone is not classified as hazardous according to the UN GHS revision 8. It does not carry any specific GHS label elements or hazard statements. In case of accidental exposure, first-aid measures such as providing fresh air, rinsing with water, and consulting a doctor if necessary are recommended. The chemical is stable under normal conditions and does not pose significant risks to human health or the environment. Proper handling and storage precautions are advised to ensure safe usage. ³

Reference

1. (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one. National Center for Biotechnology Information, 2023, PubChem Compound Summary for CID 11805069.

2. 2'-C-methyl substituted nucleoside compound and its preparation and use. Chinese Academy of Sciences Shanghai Pharmaceutical Institute, 2019, CN109748943.

3. 2-C-Methyl-D-ribono-1,4-lactone Safety Data Sheets. Echemi, 2019.