3,272. If the Wine Has Turned
Terumos 5:22
Let’s say that someone took a cask of wine as terumah for wine but it was found to be vinegar. If it’s known that it was vinegar before it was taken as terumah, then it’s not terumah. If it turned to vinegar after being taken as terumah, then it is terumah. In a case of doubt, what he took is terumah but he must take terumah again. The same rules apply if one took a gourd as terumah and it’s found to be bitter or if one takes a watermelon as terumah and it’s found to be spoiled or pierced (possibly by a snake, rendering it inedible). If one took a cask of wine as terumah and it was found to have been left open, rendering it prohibited to drink, it is terumah but he must take terumah again. In these cases of taking terumah twice, neither renders other produce meduma (a mixture of terumah and regular produce) by itself, nor must one who eats only one of them repay an extra fifth (i.e., each is treated as doubtful terumah).
Terumos 5:23
Pursuant to the previous halacha, if one of these two terumos fell into regular produce, it does not render it meduma. If the other fell in, it also does not create meduma. But if both fell in, then the produce into which they fell is rendered meduma, though only proportionate to the smaller of the two terumos. Similarly, if a non-kohein ate both of them, he must repay the value of the smaller one, including the extra fifth. When one has two such terumos, he should give both to the same kohein, who pays for the larger one.