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An overhead view of a pineapple upside down cake with pineapple chunks on top.

Caramelized Pineapple Upside Down Cake

There is a double dose of pineapple on this cake. Using pineapple chunks will let you pack in more pineapple into every inch of the cake. We didn't skimp on the caramelized brown sugar sauce either. There is an extra-large dose of that sweet sticky sauce because it's the best part of a pineapple upside-down cake.
4.57 from 16 votes
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Prep Time: 15 minutes
Cook Time: 48 minutes
Total Time: 1 hour 3 minutes
Servings: 12 servings
Calories: 391kcal
Author: Dahn Boquist

Ingredients

Pineapple Topping

  • 2 cans 20 ounces each pineapple chunks
  • 8 tablespoons butter
  • 1 cup light brown sugar

For the Cake

  • 1-⅓ cups all-purpose flour
  • 1 teaspoon baking powder
  • ¼ teaspoon baking soda
  • ¼ teaspoon salt
  • 8 tablespoons butter softened
  • ¾ cup sugar
  • 2 eggs room temperature
  • ½ cup sour cream
  • ¼ cup pineapple juice from the can of pineapples
  • 1 teaspoon vanilla extract

Instructions

  • Preheat the oven to 350°F. Line a 9-inch round cake pan with parchment paper.

To Make the Topping

  • Melt the butter in a saucepan then stir in the brown sugar until it dissolves. Remove from heat. Drain the pineapple and reserve 1/4 cup of the juice for the cake batter.
    Pat the pineapple chunks with some paper towels to remove as much of the moisture as you can. Arrange both cans of the pineapple chunks in the bottom of the cake pan.
    Pour the brown sugar mixture over the pineapple. Use a knife or spatula to spread the sugar mixture over the pineapple to get it in all the nooks and crannies. 

To Make the Cake

  • Combine the flour, baking powder, baking soda, and salt in a small dish. Whisk or sift the mixture until there are no lumps. Set aside.
  • Place the butter and sugar in a mixing bowl and beat with an electric mixer until light and creamy. Add the eggs one at a time and beat well between each addition. Beat in the sour cream then add the pineapple juice and vanilla extract. Beat well. 
  • Add the flour mixture to the batter and use a wide spatula to lightly fold the flour into the batter. 
  • The batter will be thick. Use a spatula or spoon to dollop the cake batter over the pineapple topping in the cake pan. 
  • Bake for 45 to 50 minutes or until you can stick a toothpick into the center and it comes out clean and the cake springs back when lightly pressed in the center. 
  • Remove the cake from the oven and run a thin knife around the edges of the cake pan. While the cake is still warm, invert it onto a serving platter.
    Let the cake pan remain over the cake for a few seconds to give the sticky fruit topping a chance to settle then lift the cake pan off the cake. Remove the parchment paper and let the cake cool completely before serving. 

Notes

  • When you add the flour mixture to the cake batter, do not use the electric mixer to blend the flour into the batter. Just gently fold the flour into the batter with a spatula. If you mix it with the mixer, it will develop gluten and make the cake tough. 
  • Invert the cake while it is still warm. If the cake cools down too much the fruit topping will stay stuck to the bottom of the pan. You can let the cake cool enough so it is comfortably warm and won't burn you when you flip the pan over.
  • If you don’t use parchment paper and some of the fruit topping sticks to the bottom of the cake pan when you remove the cake, just scrape the topping out of the pan and place it on top of the cake. 

Nutrition

Serving: 1 | Calories: 391kcal | Carbohydrates: 53g | Protein: 5g | Fat: 18g | Saturated Fat: 11g | Polyunsaturated Fat: 6g | Trans Fat: 1g | Cholesterol: 77mg | Sodium: 253mg | Fiber: 1g | Sugar: 28g