444. The Oily Boid: The prohibition against eating second tithe oil outside Jerusalem
…and your oil… (Deuteronomy 12:17)
If you grow olives, the oil is also subject to the laws of maaser sheini and also must not be consumed outside Jerusalem.
One might think that since our verse prohibits eating three things outside of Jerusalem that it is a "lav she'b'klalos" a negative commandment that prohibits several different things (see, for example, Mitzvah #70). However, that is not the case. Actually, grain, wine and oil are three separate things prohibited individually. Therefore, if someone ate all three of these outside Jerusalem, he would be in violation of three injunctions.
This mitzvah only applies when the maaser sheini is in effect. It is the topic of the Mishnaic tractate of Maaser Sheini and is discussed in the Talmud in tractates Makkos (17a) and Kerisos (5a). This mitzvah is codified in the Mishneh Torah in the second chapter of Hilchos Maaser Sheini and is #143 of the 365 negative mitzvos in the Rambam’s Sefer HaMitzvos.