Our understanding of the factors determining the bioavailability of carotenoids from fruits and vegetables is poor. The apolar nature of carotenoids precludes their simple diffusion from the food structure to the absorption site at the enterocyte. Therefore, there is interest in the potential pathways for solubilization in the gut before absorption. We have studied the transfer of carotenoids from carrot juice and homogenized spinach into lipid phases that mimic the intestinal lumen at the start of digestion. In this paper we report on their transfer into olive oil under conditions pertaining to the gastric environment. A comparison between preparations of raw spinach and of carrot, in which the intact cells have been largely broken, suggests that the membrane-bound carotenoids of spinach are more resistant to transfer than the crystalline carotenoids of carrot. Lowering the pH and pepsin treatment enhance the transfer from raw vegetables. The process of blanching and freezing spinach destroys the chloroplast ultrastructure and leads to (i) a substantial increase in transfer of the carotenoids to oil and (ii) an attenuation or reversal of the enhancement of transfer seen with reduced pH or with pepsin treatment. Similar effects are seen after blanching carrot juice. Our results show that removal of soluble protein and denaturation of membrane proteins enhances the partition of carotenoids into oil. For both vegetables there is no evidence of preference in the extent of transfer of one carotenoid over another. This suggests that partitioning into oil under gastric conditions is not the stage of digestion that could lead to differences in carotenoid bioavailability.