Preheat the oven to 350°, and grease a round 9x2-inch cake pan.
Pour the melted butter into the prepared pan, and sprinkle the brown sugar around the base of the pan evenly.
4 tablespoons unsalted butter, ⅓ cup light brown sugar
Arrange the pineapple slices in an even layer on top of the brown sugar: one in the center, and six around the center pineapple slice. Place a cherry in the middle of each pineapple ring, and one between each ring around the edge of the pan. Set the cake pan aside.
In a medium bowl, whisk together the flour, baking powder, and salt.
1 ½ cups all-purpose flour, 2 teaspoons baking powder, ¼ teaspoon salt
In a separate large bowl, whisk together the oil and sugar. Add the eggs, one at a time, and whisk until they’re combined. Then, add the vanilla extract and pineapple juice. Continue whisking until everything is well mixed.
¾ cup canola oil, 1 cup granulated sugar, 2 large eggs, 1 teaspoon pure vanilla extract, ½ cup pineapple juice
Add ⅓ of the dry ingredients along with the Greek yogurt into the wet ingredients, and stir with a wooden spoon or spatula. Add the remaining dry ingredients, and stir until the dry ingredients are just combined and no flour streaks remain.
¼ cup Greek yogurt
Pour the cake batter evenly into the prepared cake pan over the pineapple and cherries. Bake for 45-50 minutes, or until a toothpick inserted in the center of the cake comes out clean. Rest the cake on a cooling rack for 15 minutes.
Run a knife around the edge to loosen the cake. Place a large plate or platter upside down over the cake, then flip them both over. (The cake pan will be hot, so make sure to use oven mitts.)
Tap the cake pan to make sure the pineapples release, and slowly lift up the cake pan. (The cake and pineapple rings should come out easily, but if any rings or cherries get stuck to the bottom of the pan, you should be able to peel them off and place them on the cake.)
Allow the cake to rest an additional 20-30 minutes before slicing. See post for storage options.
Notes
The calories listed are an approximation based on the ingredients in the recipe card and a serving size of 1 slice of cake. Actual calories will vary.
Nutrition Facts
Pineapple Upside Down Cake
Serving Size
1 slice
Amount per Serving
Calories
525
% Daily Value*
Fat
28
g
43
%
Saturated Fat
6
g
30
%
Trans Fat
0.3
g
Polyunsaturated Fat
6
g
Monounsaturated Fat
15
g
Cholesterol
56
mg
19
%
Sodium
141
mg
6
%
Potassium
248
mg
7
%
Carbohydrates
66
g
22
%
Fiber
2
g
8
%
Sugar
46
g
51
%
Protein
5
g
10
%
Vitamin A
264
IU
5
%
Vitamin C
6
mg
7
%
Calcium
84
mg
8
%
Iron
2
mg
11
%
* Percent Daily Values are based on a 2000 calorie diet.