Description

This Bourbon Pineapple Upside Down Cake is a decadent twist on a classic dessert, featuring caramelized pineapple rings infused with a rich bourbon brown sugar glaze. Moist and tender cake layers are flavored with vanilla and pineapple juice, making a perfect balance of sweet, boozy, and tropical notes. Ideal for an indulgent treat or special occasion.

Ingredients

Scale

Bourbon Brown Sugar Topping

1/2 cup (1 stick) unsalted butter
3/4 cup light brown sugar
1 teaspoon vanilla bean paste or vanilla extract
4 tablespoons pineapple juice (reserved from canned pineapple slices)
3 tablespoons bourbon
20 ounce canned pineapple slices in pineapple juice, juice reserved

Cake Batter

1 1/2 cups all-purpose flour
1/2 cup white granulated sugar
2 teaspoons baking soda
1 teaspoon baking powder
1 teaspoon kosher salt
1/2 teaspoon ground cinnamon
2 large eggs
1 cup vegetable oil or canola oil
8 ounces full-fat sour cream
2 teaspoons vanilla extract
1/4 cup pineapple juice (from reserved pineapple juice)

Instructions

Preheat and prepare pan: Preheat your oven to 350°F (175°C). Generously butter or spray a 10-inch round cake pan to prevent sticking, then set it aside.
Make the bourbon brown sugar topping: In a small saucepan over medium heat, melt the butter. Once fully melted, whisk in the brown sugar until combined. Add vanilla bean paste or extract and 4 tablespoons of the reserved pineapple juice. Let this mixture simmer gently for about 2 minutes, stirring occasionally.
Add bourbon and pineapple slices: Turn off the heat and carefully pour in the bourbon while stirring. The mixture will bubble briefly due to the alcohol. Then add the pineapple slices to the saucepan, coating each ring thoroughly in the sauce. Let this mixture rest while you prepare the cake batter.
Prepare the cake batter: In a medium bowl, whisk together the flour, granulated sugar, baking soda, baking powder, salt, and cinnamon until fully combined. In a separate large bowl, whisk together the eggs, oil, sour cream, vanilla extract, and 1/4 cup pineapple juice until smooth. Gently fold the dry ingredients into the wet ingredients with a rubber spatula until just combined; avoid overmixing.
Assemble the cake: Pour a thin layer of the bourbon brown sugar sauce into the bottom of the prepared cake pan to coat it evenly. Arrange the pineapple slices over the sauce; overlap or cut slices as needed to fit them all in a single layer. Pour the remaining sauce evenly over the pineapple rings. Carefully pour the cake batter on top and spread evenly using an offset spatula or spoon.
Bake and serve: Bake the cake in the preheated oven for about 45 minutes, or until a toothpick inserted into the center comes out clean. Allow the cake to cool in the pan for at least 10 minutes, then invert it onto a large plate or cake stand, being mindful as juices may run. Slice and serve warm for best flavor and texture. Enjoy!

Notes

Use full-fat sour cream for a moist and rich cake texture.
The bourbon adds warmth and flavor but can be omitted or substituted with vanilla extract for a non-alcoholic version.
For even better flavor, you can toast the pineapple slices lightly before adding them to the sauce.
Letting the cake sit a little before inverting makes it easier to release from the pan.
Serve warm with a scoop of vanilla ice cream for an extra special dessert.

Prep Time: 20 minutes
Cook Time: 45 minutes
Category: Dessert
Method: Baking
Cuisine: American

Keywords: Bourbon Pineapple Upside Down Cake, pineapple cake, upside down cake, bourbon dessert, caramelized pineapple cake, moist cake, easy cake recipe