A chemistry-based parameter has been sought for determining the gradation of compression wood (CW), i.e., the severity, in tissues of Pinus radiata wood. Fluorescence microscopy was the reference for characterisation of the tissues containing CW. The collected material contained CW of varying severity, beginning with normal wood (NW containing no CW), continuing with material with some features of CW (CW of mild severity, MCW) and ending up with a material with pronounced features of CW (CW of high severity, SCW). Matching opposite wood (OW) was also included in the study. The chemical analyses included lignin determination, sugar analysis in the acid hydrolysate, thioacidolysis, 31P-NMR spectroscopic analysis and steric exclusion chromatography of thioacidolysis products. As the severity of CW changed progressively from NW through MCW to SCW, all chemical parameters changed concurrently. In particular, levels of galactose and lignin increased, while those of glucose and mannose decreased. The amounts of p-hydroxyphenyl β-ethers released by chemical degradation and uncondensed p-hydroxyphenyl C-9 units also increased at elevated CW severity levels. The amounts of galactose and the p-hydroxyphenyl content of the lignin correlated linearly with lignin for CW samples. The chemical differences between CW and OW in the stem, branch and seedling were similar, i.e., they are independent of the morphological origin of the sample. Parameters based on the p-hydroxyphenyl unit content appear the most suitable chemical indicators of CW severity, as they are least sensitive to the sample's morphological origin and their response to CW severity is high.