In 1898, Otto Ruff published his work on the transformation of D-Glucose to D-Arabinose later called the Ruff degradation. In this reaction, D-Glucose is converted to D-Arabinose . In this reaction, the terminal aldehyde group is converted to a carboxylic acid group, using selective oxidation of the aldehyde using Bromine water and then converted to gluconate ion. Next, Fe(OAc)₃ with 30% of H₂O₂ is added.

Thus COO- ion will form CO2 and a stereo selective compound will form. And below -CH2OH will convert to -CHO group, thus forming D-Arabinose.