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Caramelized Pineapple Upside Down Cake

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Caramelized Pineapple Upside Down Cake is sweet, sticky, and extra delicious with a double dose of that caramel-pineapple flavor! We use pineapple chunks in our version instead of whole pineapple slices which means you will get a cake that has a sweet pineapple topping layered onto every inch!

A slice of pineapple upside down cake with pineapple chunks.

Pineapple Upside Down Cake is an old-fashioned favorite, one that begs to be made every once in a while when you need a small slice of something sweet and nostalgic. It’s easy to make and features a hard-to-beat flavor combination that results in a buttery, rich, and tender cake that is baked right on its topping, a sticky caramelized pineapple (so good on its own, might I add).

It’s the best pineapple upside down cake in our opinion- and we don’t say that lightly! – because each bite gives you a double dose of pineapple and that gooey brown sugar sauce. Will you need seconds? YES.

This cake is a classic, but have you ever wondered what is the origin of pineapple upside down cake? Apparently, its beginnings are somewhat unknown, but it is believed to have first appeared in the 1920’s when recipes appeared in some mainstream publications.

Its origins are also partly related to James Dole (founder of the Hawaiian Pineapple Company now known as Dole) who invented canned pineapple, making it more accessible to Americans, and eventually, a pineapple cake recipe was born!

A pineapple upside down cake with a cup of coffee in the background.

The Ingredients:

This caramelized pineapple upside down cake from scratch only takes 15 minutes to prep! The caramelized pineapple topping is quick and easy to make, and the cake is just as simple.

Here is a quick list of the main ingredients you will need:

  • Pineapple chunks. We use two, 20-ounce cans. Maximum pineapple flavor!
  • Butter. For the pineapple topping and for the cake.
  • Brown sugar. Where the magic happens. Cooked with the pineapple and butter, it becomes a sweet and sticky with deep caramel flavor. YUM.
  • Dry ingredients. Your basic cake staples- all-purpose flour, baking powder and baking soda, sugar.
  • Eggs. Make sure yours are at room temperature.
  • Sour cream. Using a 1/2 cup of sour cream adds a touch of flavor and creaminess to the cake but it’s our secret to getting a cake ultra tender.
  • Flavor add-ins. We use pineapple juice and vanilla! Don’t drain the juice from the can. Save 1/4 cup to use in the cake for extra sweet pineapple flavor.

The Process:

Our pineapple upside down cake recipe requires three basic steps: make the pineapple topping, stir up the cake batter, and bake the cake.

  1. Make the pineapple topping: Melt the butter in a saucepan then stir in the brown sugar until it dissolves. Arrange all of the pineapple chunks in the bottom of the cake pan and pour the brown sugar mixture over the pineapple.
  2. Make the cake: Combine the dry ingredients in a small bowl then mix the wet ingredients in another bowl. Add the flour mixture and use a spatula to fold it in.
  3. Bake the cake: You will know the cake is done when a toothpick inserted into the center comes out clean and the cake springs back to the touch.
Pouring brown sugar mixture over pineapple chunks in a cake pan.
pour the brown sugar sauce over the pineapple chunks

Pro Tips for Success:

  • Line the bottom of the pan with parchment before you begin.
  • Pat the pineapple chunks with paper towels to remove as much moisture as possible.
  • Adding in the flour: Don’t use the mixer to blend the flour into the batter. Instead, gently fold it in with a spatula. This method prevents the cake from developing gluten, which can create a tough cake.
  • The batter will be thick. Use a spatula or spoon to dollop the cake batter onto the pineapple topping.
  • Inverting the cake: We do this while the cake is still warm otherwise the fruit topping could stick to the bottom of the pan. The cake doesn’t have to be piping hot fresh out of the oven, though. You can let it cool enough so that the pan is comfortably warm to the touch and won’t burn you.
  • After you invert the cake, hold the pan in place for a few seconds to give the fruit topping a chance to settle and drip down onto the cake. Remove the parchment paper and let the cake cool completely before serving.
Spooning cake batter over the caramelized fruit topping in a cake pan.
spread the cake batter over the top of the pineapple

FAQs:

  • How do you keep pineapple upside down cake from getting soggy? Make sure you dab the pineapple chunks with paper towels to remove any excess moisture. Remove as much as you can. If there is too much moisture, it will cook into your cake and could possibly turn the cake soggy.
  • Why use parchment paper? The parchment paper makes inverting the cake so much easier! If you don’t have any, you can grease/flour the edges of the cake pan. And if some of the fruit topping sticks to the bottom of the pan when you invert the cake, simply scrape it out and place it back on top of the cake.
  • Should I put my pineapple upside down cake in the fridge? Pineapple upside down cake stores best in the refrigerator, covered with a sheet of plastic wrap. Stick toothpicks into the cake to hold up the plastic wrap so it doesn’t cling to the pineapple topping.
An overhead view of a pineapple upside down cake with pineapple chunks on top.

This easy pineapple upside down cake recipe is simple to follow and results in a rich butter cake with a tender crumb. Plus, who can resist that deep caramel-pineapple topping?! Certainly not us. 😉 It hits all the right flavor notes and makes the perfect after-dinner treat!

A slice of pineapple cake with a fork.

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Some Other Recipes We Are Sure You Will Love:

  • Grilled Pineapple with Cinnamon Sugar: Strips of pineapple coated in cinnamon and sugar get caramelized over the grill and makes a healthy, fat-free dessert with so much flavor!
  • Pineapple Chicken Salad with Curry Dressing: A delicious curry-mayo chicken salad that is heaped into half a pineapple shell for serving! This is delicious, fun, and perfect for a light summertime brunch or lunch.
  • Lemon Ricotta Cake: Lovely lemon flavor paired with a moist and tender crumb, this cake is part cheesecake, part butter cake, and 100% amazing.

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

Caramelized Pineapple Upside Down Cake

Yield: 12 servings
Prep Time: 15 minutes
Cook Time: 48 minutes
Total Time: 1 hour 3 minutes

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.

Ingredients

Pineapple Topping

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

For the Cake

  • 1-1/3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 8 tablespoons butter, softened
  • 3/4 cup sugar
  • 2 eggs, room temperature
  • 1/2 cup sour cream
  • 1/4 cup pineapple juice (from the can of pineapples)
  • 1 teaspoon vanilla extract

Instructions

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

To Make the Topping

  1. 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

  1. 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.
  2. 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. 
  3. Add the flour mixture to the batter and use a wide spatula to lightly fold the flour into the batter. 
  4. The batter will be thick. Use a spatula or spoon to dollop the cake batter over the pineapple topping in the cake pan. 
  5. 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. 
  6. 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 Information:
Yield: 12 Serving Size: 1
Amount Per Serving: Calories: 391Total Fat: 18gSaturated Fat: 11gTrans Fat: 1gUnsaturated Fat: 6gCholesterol: 77mgSodium: 253mgCarbohydrates: 53gFiber: 1gSugar: 28gProtein: 5g

Nutrition information is a guideline only, is calculated automatically by third-party software, and absolute accuracy is not guaranteed.

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