Cancer is one of the main causes of death in both men and women, claiming over 6 million people each year worldwide. Chemoprevention in combination with anti-cancer treatment is therefore important to reduce morbidity and mortality. Stilbene-based compounds have over the years attracted attention of many researchers due to their wide ranging biological activities. One of the most relevant and extensively studied stilbenes is trans-resveratrol, a phytoalexin present in grapes and other foods. One of the most striking biological activities of trans-resveratrol soundly investigated during recent years has been its cancer-chemopreventive potential. It has been found that the biological activity of trans-resveratrol and its analogues depends significantly on the structural determinants, which are (i) number and position of hydroxyl groups, (ii) intramolecular hydrogen bonding, (iii) stereoisomery and (iv) double bond. The observation that trans-stilbene compounds having 4 -hydroxy group, double bond and bearing ortho-diphenoxyl or para-diphenoxyl functionalities possess remarkably higher chemopreventive activity than trans-resveratrol gives us useful information for further chemopreventive drug design.