If one set aside a gourd as <i>Terumah</i> [produce consecrated for priestly consumption] and it was found to be bitter, a melon and it was found to be rotten, it is [considered valid] <i>Terumah</i> but he must again give <i>Terumah</i>. If one set aside a barrel of wine as <i>Terumah</i> and it was found to be vinegar, if it was known to be vinegar before he set it aside as <i>Terumah</i>, is is [not considered valid] <i>Terumah</i>. But if it had become vinegar after he had given it as <i>Terumah</i>, behold it is <i>Terumah</i>. In a case of doubt, it is <i>Terumah</i> but he must again give <i>Terumah</i>. The first [set of <i>Terumah</i>] will not render on its own [another substance that it falls into] <i>Demai</i> [produce from which it is uncertain if tithes are already taken] and does not require a fine of a fifth [of its value if eaten by an Israelite], and so too with the second [set of <i>Terumah</i>].
Tosefta Terumot
Vegetables that they are accustomed to watching over for one day [after they are harvested, before they begin to spoil], they they take terumah on their behalf for one day; two days, they take terumah on their behalf for two days; three days, they take terumah on their behalf for three days. The cucumber, the pumpkin, the "kitchen vegetables" (=טרכסמין, esp. endive, see Jastrow), and beets are what they are accustomed to watching over for one day [and] they take terumah on their behalf for one day. The lettuce, and the leek, and the turnip, and the carob are what they are accustomed to watching over for two days, [and] they take terumah on their behalf for two days. The scallions and the sweet melons are what they are accustomed to watching over for three days, [and] they take terumah on their behalf for three days. This is the general rule: Everything is watched over, we [may] take terumah on its behalf. Rabbi Nechemiah says, we do not take terumah from mulberries that are harvested in the morning on behalf of mulberries that are harvested in the evening. And so too Rabbi Yosei would say, there is no bitterness in cucumbers except for its innermost part -- behold, this one supplements the outer layer [of the cucumber with additional non-bitter produce, presumably equivalent to the bitter area inside the cucumber] and thereby takes terumah.
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Tosefta Terumot
One who takes terumah from a [wine] tank and finds it uncovered, or a watermelon and finds it to have bite marks (Ter. 8:6), it is [valid] terumah, but he goes back and takes terumah [a second time, as the first terumah involved hazardous conditions]. [Apropos of wine,] Rabbi Yishmael son of Rabbi Yosei says in the name of his father, we take terumah from wine on behalf of vinegar, but we do not take terumah of vinegar on behalf of wine, except according to the proportion.
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Tosefta Terumot
[If] he had in his heart (i.e., he intended) to take terumah of wine on behalf of wine, but what he had in his hand was vinegar, his terumah is not [valid] terumah. If he had wine in his hand, he takes terumah from the wine, and he goes back and takes terumah from the vinegar. If he had checked the barrel in order to separate [terumah] on its behalf, and then he returns and finds it has turned to vinegar: [If] three days or less [had transpired between the first and second check], it is [considered] certainly untithed produce, and from [three days and up] there is a doubt. But [as to] wine from a vat we may separate terumah on its behalf with the presumption that it remains wine for up to 40 days.