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Pineapple Upside Down Cake
5 from 252 votes

Pineapple Upside Down Cake

This Pineapple Upside Down Cake features a buttery brown sugar base topped with pineapple rings and maraschino cherries, flipped over a moist cake incorporating pineapple juice and sour cream. The presentation showcases caramelized fruit slices with a tender, lightly sweet crumb cake beneath.

Prep Time
20 mins
Cook Time
45 mins
Cake cooling
20 mins
Servings: 10 - 12 people
Calories: 319 kcal
Course: Cake
Cuisine: American

Ingredients

Topping:
  • 565g/ 20 oz pineapple not in syrup, Note 1, canned slices in juice
  • 12 - 18+ maraschino cherries (Note 2)
  • 60g/ 4 tbsp butter melted, unsalted
  • 1/2 cup brown sugar
CAKE:
  • 1 1/2 cups flour
  • 1 tsp baking powder
  • 1/4 tsp baking soda (sub 1 tsp baking powder)
  • 1/4 tsp salt
  • 1/3 cup milk , full or low-fat
  • 1/4 cup pineapple juice , reserved from can (under Topping ingredients)
  • 1/4 cup sour cream , full fat (sub plain yogurt)
  • 1 tsp vanilla extract (or essence)
  • 115g/ 1 stick butter , unsalted, softened (to 18C/64F, Note 3)
  • 3/4 cup white sugar
  • 2 egg at room temperature (Note 4, large
  • pineapple chopped (Note 1, leftover

Instructions

    Cup of Yum
  1. Preheat oven to 180°C/350°F (160°C fan).
Pineapple decorative top:
  1. Dry fruits: Line a tray with paper towels or a tea towel, then place pineapple and cherries on. Pat dry with paper towels.
  2. Butter: Pour melted butter into a 23cm/9" cake pan at least 5cm/2" deep. (Not springform, as they'll leak.) Brush butter up the sides.
  3. Brown sugar: Sprinkle sugar over the base, roughly spreading it out (use the brush).
  4. Arrange pineapple: Place one pineapple ring in the centre, then surround with either halved pineapple rings (as pictured), or whole ones.
  5. Decorate with cherries as desired. Most people just put them in the middle of the pineapple rings.
  6. Press cherries and pineapples down firmly so they are in direct contact with the base of the cake pan - so you get vibrant red and yellow colour pops at the end, not tarnished by caramel. (Note 5)
Batter:
  1. Flour Mixture: Whisk flour, baking powder, baking soda and salt in a bowl.
  2. Milk Mixture: Whisk milk, sour cream, pineapple juice and vanilla in a 2nd bowl.
  3. Cream butter and sugar: In a third (final!) bowl, beat the butter and sugar for 2 minutes on speed 7 (handheld mixer) until fluffy.
  4. Eggs: Add eggs one at a time, beating for 20 seconds in between.
  5. Add Flour Mixture then Milk Mixture, alternating: Add 1/3 of the Flour Mixture, then mix in using a rubber spatula. Add 1/2 the Milk Mixture, mix in. Add half the remaining Flour Mixture, mix. Add all the remaining Milk Mixture, mix. Then mix in the last of the Flour Mixture. Stir in the leftover pineapple pieces.
  6. Fill pan: Spread batter over pineapple layer, smooth and level the surface.
  7. Bake: Bake for 30 minutes. Remove, loosely cover with foil, then bake for a further 15 minutes until a toothpick inserted into the centre comes out clean.
Turning out cake:
  1. Cool 20 minutes: Remove cake from oven and leave inside pan to cool for 20 minutes.
  2. Flip! Run a butter knife around the inner edge of the cake pan. Put a plate or serving platter over the cake, then flip. Tap base / shake pan gently then lift slowly. Voila!
  3. Cool completely before serving.

Notes

  • Use canned pineapple packed in juice, not syrup, to control sweetness and utilize the juice in the batter.
  • Ensure butter is softened but not overly soft (around 18°C / 64°F) for ideal creaming and cake texture.
  • Room temperature eggs blend more evenly into the batter; warming cold eggs in warm water briefly can help.
  • Press pineapple rings and cherries firmly into the butter and brown sugar base to keep bright colors visible after baking.
  • The cake keeps well refrigerated for at least five days; bring to room temperature before serving for optimal flavor.

Nutrition Information

Calories 319cal (16%) Carbohydrates 47g (16%) Protein 3g (6%) Fat 14g (22%) Saturated Fat 8g (40%) Trans Fat 1g (50%) Cholesterol 61mg (20%) Sodium 162mg (7%) Potassium 160mg (3%) Fiber 1g (4%) Sugar 34g (68%) Vitamin A 468IU (9%) Vitamin C 5mg (6%) Calcium 60mg (6%) Iron 1mg (6%)

Nutrition Facts

Serving: 10 - 12 people

Amount Per Serving

Calories 319

% Daily Value*

Calories 319cal 16%
Carbohydrates 47g 16%
Protein 3g 6%
Fat 14g 22%
Saturated Fat 8g 40%
Trans Fat 1g 50%
Cholesterol 61mg 20%
Sodium 162mg 7%
Potassium 160mg 3%
Fiber 1g 4%
Sugar 34g 68%
Vitamin A 468IU 9%
Vitamin C 5mg 6%
Calcium 60mg 6%
Iron 1mg 6%

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