110822-87-2Relevant academic research and scientific papers
Investigation of the mechanism of dissociation of glycolaldehyde dimer (2,5-dihydroxy-1,4-dioxane) by FTIR spectroscopy
Yaylayan, Varoujan A.,Harty-Majors, Susan,Ismail, Ashraf A.
, p. 31 - 38 (1998)
Glycolaldehyde represents the simplest α-hydroxycarbonyl moiety - a common structural feature of reducing sugars. It exists in solid state, only in crystalline dimeric form as 2,5-dihydroxy-1,4-dioxane. However, in solution phase or during heating, it dissociates into different dimeric and monomeric forms. FTIR spectroscopy was used to study the effect of temperature, pH and solvent on the dissociation and chemical transformations of glycolaldehyde. The infrared spectra were recorded in different solvents as a function of time and temperature (both during heating and cooling cycles) between 30 and 85°C. During heating, glycolaldehyde cyclic dimer generated two bands in the carbonyl region, one at 1744 cm-1 and the other at 1728 cm-1. These bands increased during the heating cycle and decreased during the cooling cycle. The data indicated that the glycolaldehyde cyclic dimer (2,5-dihydroxy-1,4-dioxane) undergoes a ring opening to form the acyclic dimer (1728 cm-1) that can recyclize into the 2-hydroxymethyl-4-hydroxy-1,3-dioxolane structure. The acyclic dimer can also dissociate into monomeric glycoladehyde (1744 cm-1) in equilibrium with the enediol form (1703 cm-1). There is evidence to indicate oxidation of glycolaldehyde into glycolic acid during heating, in either neutral or basic aqueous solutions.
Insights into the existing form of glycolaldehyde in methanol solution: An experimental and theoretical investigation
Li, Yuehui,Shi, Yantao,Song, Xuedan,Zhao, Zhengyan,Zhang, Naitian,Hao, Ce
, p. 8149 - 8154 (2021/05/21)
Glycolaldehyde (HOCH2CHO, GA), the simplest molecule containing both hydroxyl and aldehyde groups, is structurally the most elementary member of monosaccharide sugars, which may provide new clues for probing the origin of life on planets like the Earth. Uncovering the existing state of GA in solution systems is an important scientific issue. Generally, methanol is used as the main mobile phase in the liquid chromatography analysis of GA, but the state of GA existing in methanol solution remains unknown, thus making it difficult to analyse GA accurately. Herein, the state and dynamic equilibrium of GA in methanol solution were systematically studied by UV-visible spectroscopy, nuclear magnetic resonance (1H-NMR) spectroscopy, liquid chromatography mass spectrometry (LC-MS) and density functional theory (DFT) calculations. The results demonstrated that the equilibrium component of GA in methanol solution is different from that in aqueous solution and that glycolaldehyde hemiacetal (GAHA) is a dominant component (>90%). Laying the foundation for experimental analysis, the transformation of different components at equilibrium was studied using DFT. The results confirm that hydrogen bonding-induced proton transfer occurs between the components at equilibrium. This work provides an important reference for the analysis of sugars and related compounds in various biochemical reactions.
