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4.9 from 21 votes

Pineapple Upside-down Cake

Pineapple Upside Down Cake is as tasty as it is pretty! Made with moist yellow cake and caramelized pineapple and cherries, this classic dessert is a crowd-pleaser.

Prep Time
20 mins
Cook Time
20 mins
Total Time
1 hr 10 mins
Servings: 8 servings
Calories: 589 kcal
Course: Dessert , Baked Goods
Cuisine: American

Ingredients

For the Topping
  • 5 tablespoons butter
  • ¾ cup light brown sugar, packed
  • 2 teaspoons lemon juice
  • 7 pineapple rings
  • 7 Maraschino cherries
For the Cake
  • ½ cup butter, room temperature
  • 2 tablespoons vegetable oil
  • 1 cup granulated sugar
  • ¼ cup light brown sugar, packed
  • 2 large eggs
  • 2 cups flour
  • 1 tablespoon baking powder
  • ½ teaspoon salt
  • ¼ cup milk
  • ¼ cup sour cream
  • ¼ cup pineapple juice (from the canned pineapples)
  • 2 teaspoons vanilla extract

Instructions

    Cup of Yum
  1. In a skillet over medium heat, add the butter and brown sugar. Cook, stirring regularly, until melted and bubbling. The mixture will be grainy.
  2. Stir in the lemon juice and cook, stirring regularly, until the mixture is bubbly and fluid.
  3. Remove pan from the heat and transfer the caramel to a 9 x 4-inch round baking dish, swirling to cover the bottom of the pan.
  4. Arrange the pineapple rings in the syrup close together but not overlapping. Place a maraschino cherry in each pineapple hole. Set aside.
  5. In a large bowl, add the room-temperature butter, vegetable oil, granulated sugar, and brown sugar. Using a hand mixer at medium speed, beat until creamy.
  6. Add the eggs one at a time, beat well after each addition.
  7. In a separate bowl, sift together the flour, baking powder, and salt. 
  8. In another bowl, combine milk, sour cream, pineapple juice, and vanilla extract. Whisk until blended.
  9. Beginning and ending with the flour mixture, add flour mixture and milk mixture alternately to the egg mixture. Beat at low speed with every addition. The batter will be thick.
  10. Spoon the batter over the pineapples, carefully as not to shift or move the fruits. Using a spatula, spread and smoothen it evenly.
  11. Bake in a preheated 350 F oven for about 45 to 50 minutes or until golden brown and a toothpick inserted in the center comes out clean.
  12. Remove from the oven and run a small spatula around the cake to loosen.
  13. Place a serving platter over the baking pan and using hand mittens, carefully invert and turn out the cake onto the platter. Brown sugar topping will be very hot.

Notes

  • Pat the pineapples and cherries with paper towels to remove excess moisture that might otherwise make for an overly wet crumb.
  • As the juices might bubble up during baking, place a pan or sheet on the lower rack to catch spills. Or use a deeper pan, 9 x 4 inches.
  • Removing the cake from the pan while still hot is best, as the caramelized topping might harden and stick if completely cooled. Run a small spatula or knife around the sides to loosen and invert on a serving platter.

Nutrition Information

Calories 589kcal (29%) Carbohydrates 88g (29%) Protein 6g (12%) Fat 25g (38%) Saturated Fat 16g (80%) Cholesterol 95mg (32%) Sodium 345mg (14%) Potassium 328mg (9%) Fiber 2g (8%) Sugar 62g (124%) Vitamin A 715IU (14%) Vitamin C 5mg (6%) Calcium 131mg (13%) Iron 2mg (11%)

Nutrition Facts

Serving: 8servings

Amount Per Serving

Calories 589

% Daily Value*

Calories 589kcal 29%
Carbohydrates 88g 29%
Protein 6g 12%
Fat 25g 38%
Saturated Fat 16g 80%
Cholesterol 95mg 32%
Sodium 345mg 14%
Potassium 328mg 7%
Fiber 2g 8%
Sugar 62g 124%
Vitamin A 715IU 14%
Vitamin C 5mg 6%
Calcium 131mg 13%
Iron 2mg 11%

* Percent Daily Values are based on a 2,000 calorie diet.