The objective of this research was to investigate the effects of the conditions of hot water extraction (HWE) on abundance, properties, and structure of lignin depolymerization products. HWE of extracted softwood (ponderosa pine) was conducted using temperatures from 140 to 320°C for 90min. HWE materials were then subjected to a soxhlet extraction process using dichloromethane (DCM). The composition and molecular weight of this DCM-soluble material was conducted using semi-quantitative Py-GC/MS and ESI/MS, which showed that this material is rich in lignin with low molecular weight (<1200gmol^-1) and low polydispersity (~1.4). The highest yield of this material (~4.2%) was obtained in material processed at 260°C. Py-GC/MS of the solid fraction after the DCM process showed a progressive reduction of products of the pyrolysis of lignin as the HWE temperature increased. This finding suggests that the lignin content in the solid decreased due in part to migration from the cell walls and middle lamella to the particles surfaces, particularly the inner surface of the cells. SEM and AFM techniques helped to visualize the ability of this DCM-soluble extract to adhere to cellulosic fibers. Therefore, this lignin-rich material presents properties that depend on the conditions of the operation. Results indicate that during HWE it is possible to control the process parameters to limit or increase the amount of DCM-soluble lignin and its properties as required for downstream processes.