Pineapple Upside Down Cake Recipe

Pineapple Upside Down Cake Recipe

Introduction

Did you know that the Pineapple Upside Down Cake surged to iconic popularity in the 1920s after Dole sponsored a national recipe contest? This classic dessert has remained a beloved staple in American homes for nearly a century. But what is it about this particular Pineapple Upside Down Cake recipe that makes it so irresistibly perfect for any occasion? The secret lies in the harmonious balance of a deeply caramelized, buttery brown sugar topping with the bright, tangy sweetness of pineapple rings, all resting on a supremely moist and fluffy vanilla cake base. This retro dessert isn’t just a treat; it’s a centerpiece that promises smiles and nostalgia with every beautiful slice. Let’s dive into creating this masterpiece, which combines simplicity with stunning visual appeal, all baked to perfection in a single pan.

Ingredients List

Gather these simple ingredients for a cake that’s bursting with flavor and texture. Using high-quality, room-temperature ingredients is key to a perfect crumb.

  • For the Caramelized Topping:
    • 1/2 cup (115g) Unsalted Butter – Melted. This creates the rich, golden caramel base. For a nuttier flavor, you can use browned butter.
    • 1 cup (200g) Packed Light Brown Sugar – The molasses notes are essential for that deep, caramel flavor. Dark brown sugar can be used for an even richer taste.
    • 1 can (20 oz) Pineapple Rings in Juice – Drained, reserving 1/4 cup of the juice for the cake batter. The rings should be patted dry to prevent a soggy topping. Fresh pineapple can be used, but must be thinly sliced and pre-cooked slightly to soften.
    • 1 jar (6 oz) Maraschino Cherries – Drained. Their vibrant red color and sweet pop are the classic finishing touch.
  • For the Vanilla Cake:
    • 1 1/2 cups (190g) All-Purpose Flour – Spooned and leveled for accuracy.
    • 1 1/2 tsp Baking Powder – For that essential lift and fluffy texture.
    • 1/4 tsp Salt – Balances the sweetness and enhances all flavors.
    • 1/2 cup (115g) Unsalted Butter, softened – Should be soft to the touch for easy creaming.
    • 1 cup (200g) Granulated Sugar
    • 2 Large Eggs – Room temperature. They incorporate more easily, creating a smoother, more voluminous batter.
    • 1 tsp Pure Vanilla Extract – Use the real stuff for the best aroma.
    • 1/2 cup (120ml) Whole Milk – Room temperature. For a lighter cake, you can substitute with buttermilk for a slight tang.
    • 1/4 cup (60ml) Reserved Pineapple Juice – This is the secret ingredient that infuses the entire cake with a subtle tropical tang.

Timing

Prep Time
20 minutes
Cook Time
45-50 minutes
Total Time
About 1 hour 10 minutes (plus cooling)

Compared to many layer cakes that require extensive decorating, this Pineapple Upside Down Cake is remarkably efficient. The active prep time is under 30 minutes, with most of the work happening in the oven. The total hands-on time is about 25% less than the average frosted cake recipe, making it an excellent choice for bakers of all levels who want impressive results without a full day in the kitchen.

Pineapple Upside Down Cake Recipe

A stunning, golden-brown Pineapple Upside Down Cake fresh from the oven, showcasing its caramelized pineapple and cherry topping.

Step-by-Step Instructions

Step 1: Prepare the Pan and Topping

Preheat your oven to 350°F (175°C). Take a 9-inch round cake pan (or a 10-inch cast-iron skillet for a rustic look) and generously grease the sides. In a small bowl, combine the 1/2 cup of melted butter and the packed brown sugar. Stir until it forms a thick, gritty paste. Pour this mixture into the bottom of your prepared pan and use a spatula or the back of a spoon to spread it into an even layer. This is the foundation of your caramel topping—don’t rush it. Now, arrange the well-drained pineapple rings in a single layer over the sugar-butter mixture. Place a maraschino cherry in the center of each ring and in any gaps between rings. This step is where your cake gets its signature beautiful look, so take a moment to create a pattern you love.

Step 2: Make the Cake Batter

In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside. In a large mixing bowl, use an electric mixer on medium speed to beat the softened butter and granulated sugar together for 2-3 minutes. You’re looking for a light, pale, and fluffy consistency—this step incorporates air, which is crucial for a tender cake. Beat in the eggs, one at a time, ensuring each is fully incorporated before adding the next. Mix in the vanilla extract. Now, with your mixer on low speed, add about one-third of the flour mixture, followed by half of the milk. Repeat, ending with the final third of the flour. Finally, gently stir in the reserved 1/4 cup of pineapple juice just until the batter is smooth and uniform. Be careful not to overmix, as this can develop the gluten and lead to a tough cake.

Step 3: Assemble and Bake

Carefully spoon the cake batter over the arranged pineapple and cherries in your pan. Use an offset spatula or the back of a spoon to gently spread the batter into an even layer, being careful not to disturb the decorative fruit pattern underneath. Tap the pan lightly on the counter to release any large air bubbles. Place the pan in the center of your preheated oven and bake for 45 to 50 minutes. The cake is done when the top is golden brown, the edges pull slightly away from the pan, and a toothpick inserted into the center of the cake (not through a pineapple ring) comes out clean or with a few moist crumbs.

Step 4: The Magic Flip

This is the most critical moment! Remove the cake from the oven and place it on a wire cooling rack. Do not let it cool in the pan for more than 5-10 minutes. If it cools completely, the caramel will solidify and stick to the pan. While the cake is still very warm, run a thin knife or offset spatula around the edges to loosen it. Place a large, heat-proof serving plate or platter upside down over the cake pan. Using oven mitts, firmly hold the plate and pan together and confidently flip them over in one swift motion. Gently lift the cake pan away. If any fruit sticks, simply use a spatula to place it back on the cake. Allow the cake to cool for at least 30 minutes before slicing to let the caramel set slightly.

Nutritional Information

The following estimates are for one serving (1/12th of the cake) and are approximate.

  • Calories: ~380 kcal
  • Total Fat: 16g
  • Saturated Fat: 10g
  • Cholesterol: 75mg
  • Sodium: 120mg
  • Total Carbohydrates: 58g
  • Dietary Fiber: 1g
  • Sugars: 45g
  • Protein: 4g

Healthier Alternatives

You can enjoy this classic with a lighter touch by making a few smart swaps without sacrificing the iconic flavor and moisture.

  • Reduce Sugar: Cut the brown sugar in the topping to 3/4 cup and use a natural sugar substitute like coconut sugar or a monk fruit blend for the cake batter.
  • Butter Substitute: For the cake batter, replace half the butter with unsweetened applesauce or mashed ripe banana to reduce fat while adding moisture.
  • Flour Power: Substitute half the all-purpose flour with whole wheat pastry flour for a fiber boost without a dense texture.
  • Dairy-Free: Use plant-based butter and unsweetened almond or oat milk. The pineapple juice ensures moisture is never an issue.
  • Fresh Fruit Boost: Use fresh pineapple rings and fresh pitted cherries (slightly macerated in a touch of maple syrup) to avoid the added sugars in canned and jarred varieties.

Serving Suggestions

This cake is glorious on its own, but a few accompaniments can elevate it to a restaurant-quality dessert.

  • A La Mode: A scoop of vanilla bean ice cream or coconut milk ice cream melting over the warm cake is a timeless pairing.
  • Whipped Cream: A dollop of freshly whipped cream, lightly sweetened with a hint of vanilla or a teaspoon of the reserved pineapple juice.
  • Caramel Drizzle: For the ultimate indulgence, warm up some store-bought or homemade caramel sauce and drizzle it over each slice.
  • With Coffee: Serve slightly warm with a strong cup of coffee or a tropical herbal tea to balance the sweetness.
  • Brunch Star: This cake makes a fantastic centerpiece for a weekend brunch alongside savory quiches or bacon.

Common Mistakes

  • Letting the Cake Cool Completely in the Pan: This is the #1 reason for disaster. The caramel hardens and bonds to the pan. Always flip while warm.
  • Wet Pineapple: Not thoroughly draining and patting dry the pineapple rings leads to excess liquid, which can make the topping soupy and prevent proper caramelization.
  • Overmixing the Batter: Once the flour is added, mix only until just combined. Overmixing develops gluten, resulting in a tough, dense cake.
  • Using Cold Ingredients: Eggs, butter, and milk should be at room temperature to emulsify properly and create a smooth, high-volume batter.
  • Underbaking: The moist fruit on the bottom can trick you. Always use the toothpick test in the cake center, not through fruit.

Storing Tips

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