Pineapple Upside Down Cake

Course Dessert

Prep Time 30

Cook Time 40

Total Time 1 10

10-inch round cake pan
Parchment paper
Digital scale (or dry measuring cups, liquid measuring cup, and measuring spoons)
Stand mixer with paddle attachment (or hand mixer with large bowl)
Sifter
Silicone spatula
Small saucepan with a heavy bottom
Toothpicks
Decorative serving plate or cake stand

14 pineapple slices (1½ 20oz cans, 567g), fresh or canned – packed in unsweetened pineapple juice
1½ cups (150g) cake flour, sifted
¾ cup (150g) granulated sugar
1 tsp (4.6g) baking powder
¼ tsp (1.3g) baking soda
¼ tsp (1.5g) salt
¼ cup (60.5g) sour cream
¼ cup (60.5g) coconut milk
2 tsp (15g) cream of coconut
9 Tbsp (128g) unsalted butter, room temperature
3 large (56g) egg yolks
1 tsp (4g) vanilla extract

Preheat the oven to 350°F/180°C.
Place the pineapple slices on a paper towel and dry both sides.
Put a circle of parchment paper in the bottom of a 10-inch cake pan. You do not need to grease or flour the cake pan for this recipe.
You can use a 9-inch cake pan for this cake as well, but it will be very full and took about 10 extra minutes to bake. I used a 9-inch cake pan when I took the pictures, but the cake turned out slightly better when using a 10- inch cake pan. For that reason, the rest of the recipe will be written for a 10-inch cake.

Place the caramel sauce ingredients in a small saucepan and heat over medium low heat while stirring constantly with a silicone spatula. Continue stirring until the mixture has just started to boil. Remove the pan from the stove and immediately pour the caramel sauce into the bottom of the prepared cake pan to stop the cooking process.

Place one whole slice of pineapple in the middle and 7 whole slices around it on the bottom of the cake pan (i.e., a total of 8 slices). Then cut the 6 remaining slices in half and place the half slices side by side against the side of the cake pan. The cut sides should be sitting in the caramel and not resting on pineapple.

Combine the flour, baking powder, baking soda, salt, and granulated sugar in the bowl of the stand mixer and mix on the lowest speed for 30 seconds to combine.
In a separate small bowl, mix together the sour cream, coconut milk, and cream of coconut. Add ¾ of the mixture and the butter to the bowl of dry ingredients. Mix on low speed until all dry ingredients are moistened. Increase the speed to medium and beat for 2 minutes. This will incorporate air into the batter. The color of the cake batter will lighten to an almost white color.
Add egg yolks and vanilla extract to the remaining sour cream mixture. Then, pour the wet ingredients into the mixing bowl in three additions. Mix until the ingredients are just incorporated after each addition.
Gently pour the cake batter into the cake pan and use the spatula to smooth the top before putting it into the oven on the bottom rack. The higher heat at the bottom of the oven will help caramelize the brown sugar sauce while baking.

Bake the cake for 40-50 minutes or until an inserted toothpick comes out clean. Immediately after taking the cake from the oven, run a silicone spatula around the sides of the pan and invert it onto a serving plate. Make sure the flat part of the serving plate is large enough to fit the whole cake pan before inverting it.
Leave the cake pan on the serving plate for 1-2 minutes before removing it. Use hand mitts when lifting the cake pan because it will still be hot. The parchment paper should make it so the fruit doesn’t stick, but if fruit remains in the pan, use a spatula to place it back on the cake.
Most of the caramel sauce should have soaked into the cake, but there might be a little sauce that drips out when flipping the cake over. Just be aware of this if using a cake plate or stand without a rim.

Pineapple Upside Down Cake is best the day it’s baked (and is delicious when it’s still warm), but it can be stored in an airtight container at room temperature for 2 days and in the refrigerator for 5 days.

This recipe was adapted from the “Pineapple Upside-Down Cake” recipe in The Cake Bible by Rose Levy Beranbaum.