c. 1400, "causing grief," also "causing pain, painful" (a sense now obsolete), from Old French doloros "painful; sorrowful, wretched" (12c., Modern French douloureux) from Late Latin dolorosus "painful, sorrowful," from Latin dolor "pain, grief," perhaps from PIE root *delh- "to chop" "under the assumption than 'pain' was expressed by the feeling of 'being torn apart'" [de Vaan].
Sense of "exciting or expressing grief or distress" is from mid-15c. Of persons or feelings, "full of sorrow," from 1510s. Related: Dolorously; dolorousness.