This classic pineapple upside-down cake features caramelized pineapple slices over a soft, buttery vanilla cake. Beautifully nostalgic and irresistibly delicious!

Pineapple Upside Down Cake on a plate and a cake stand.

My husband had requested pineapple cake and had been longing to eat it for a long, long time. Maybe that statement would make me seem like I’m not the best wife. However, he definitely knows that I’m not much of a baker, so I kind of ignored his sentiment.

Pineapple Upside Down Cake on a plate and a cake stand.

When I saw Vivianne’s Pineapple Upside-down Cake recipe on her blog, Green Cilantro, last month, I knew the time had come! My husband was really excited when I told him about my attempt. He even came to check on how I was doing in the kitchen several times (or maybe he was worried about his cake).

Pineapple Upside Down Cake on a plate with fork.

Despite a few moments of “panic” mode (details are in the recipe instructions), I think I did really well. I am not a baker, but I do have a sweet tooth and have eaten more than my share of sweets. The cake turned out to be delicious. Vivianne did not include all the caramel syrup in her recipe, being worried that it might be too sweet, but I actually poured it all in. It was not as sweet as I thought it was going to be. My husband and children loved it as well and requested to have dessert after every meal as long as there were still pieces of the cake left.

If you are not a baker like me, I would say this is “doable” for a beginner baker. Just read about my panic moment below so you won’t panic like me. Enjoy!

Pineapple Upside Down Cake

Pineapple Upside Down Cake

5 from 2 votes
This classic pineapple upside-down cake features caramelized pineapple slices over a soft, buttery vanilla cake. Beautifully nostalgic and irresistibly delicious!
Prep Time: 30 minutes
Cook Time: 1 hour
Cooling Time: 1 hour
Total Time: 1 hour 30 minutes
Servings: 1 9-inch (23 cm) cake

Ingredients
 
 

  • 1 pineapple
  • ¾ cup sugar
  • ½ cup water
  • 6 Tbsp unsalted butter (¾ stick; softened)
  • 1 cup all-purpose flour (plain flour)
  • 1 tsp baking powder
  • ¼ tsp Diamond Crystal kosher salt
  • 2 large eggs (50 g each w/o shell) (at room temperature)
  • 3 large egg yolks (at room temperature)
  • 1 cups sugar
  • 1 tsp pure vanilla extract
  • ½ cup unsalted butter (8 Tbsp, 1 stick; melted and cooled)
Japanese Ingredient Substitution: If you want substitutes for Japanese condiments and ingredients, click here.

Instructions
 

  • Before You Start…Please note that this recipe requires 1 hour of cooling time. 
    Gather all the ingredients.
    Pineapple Upside Down Cake Ingredients
  • Position a rack in the center of the oven and preheat the oven to 350ºF (177ºC). For a convection oven, reduce cooking temperature by 25ºF (15ºC). Generously butter a 9-inch (23 cm) round cake pan.
    Pineapple Upside Down Cake 9
  • Peel, halve, and core the pineapple, then cut into ¾ inch (2 cm) thick slices. Cut the slices in half. I used this pineapple slicer, which cores and slices an entire pineapple.
    Pineapple Upside Down Cake 1
  • Put ¾ cup (150 g) sugar and the water in a medium saucepan and mix well so the sugar is moistened.
    Pineapple Upside Down Cake 2
  • Place the pan over high heat and leave it undisturbed. The liquid starts to boil slowly for the first minute or two, and then it will boil rapidly after that. DO NOT TOUCH the pan until the sugar syrup starts to caramelize from the edge of the pan. When you see dark color syrup around the edge of the pan, gently swirl the pan in a circular motion so the sugar caramelizes evenly. Keep swirling gently until the caramel is a medium golden brown.
    Pineapple Upside Down Cake 3
  • When it’s medium golden brown, turn down the heat to the lowest and whisk in the 6 Tbsp butter. Quickly mix well and be careful for splutter.
    Pineapple Upside Down Cake 4
  • Carefully add the pineapple and stir until it is coated with the caramel. The caramel will become liquid again once you heat it up and the pineapple will also release juice.
    Pineapple Upside Down Cake 5
  • Turn up the heat to medium-high and bring to a boil. By this time, you see caramel is re-liquefying already. Then turn down the heat to medium-low and simmer for 10 to 12 minutes, or until the pineapple turns golden brown.
    Pineapple Upside Down Cake 6
  • Using a fork, transfer the pineapple to a plate.
    Pineapple Upside Down Cake 7
  • Continue to boil the remaining caramel on medium-high heat for few minutes, or until thick and syrupy.
    Pineapple Upside Down Cake 8
  • Arrange the pineapple in concentric circles in the prepared pan. Make sure to fill in any gaps at bottom of the pan with smaller pieces. My pineapple was just large enough to cover the bottom (so don’t eat your pineapple until you finish this step!). If you have extra pineapple, you can do double layers. Then pour the caramel syrup on top.
  • In a medium bowl, sift together the flour, baking powder, and salt.
    Pineapple Upside Down Cake 11
  • In a large bowl, beat together the eggs and egg yolks until blended, then slowly beat in the remaining 1 cup (200 g) sugar, the vanilla, and the ½ cup melted butter. Using a rubber spatula, fold the flour mixture into the egg mixture until it's completely mixed.
    Pineapple Upside Down Cake 12
  • Pour the batter evenly over the pineapple in the cake pan. Tap the pan gently on a counter top to get rid of any air bubbles in the batter.
    Pineapple Upside Down Cake 13
  • Bake at 350ºF (177ºC) for 50 to 60 minutes, or until the top is golden brown. If it becomes golden brown too quickly and not done baking yet, cover with aluminum foil so it doesn't burn. The cake is ready when you insert a skewer in the center of the cake and it comes out clean. Let cool in the pan on a wire rack for about 30 minutes.
  • Place a serving plate upside down on top of the cake pan, then holding the pan and the plate tightly together, invert them quickly (but carefully). Lift off the cake pan. If some of the pineapple are stuck to the pan, remove them and place them back on top of the cake. Let the cake cool for at least another 30 minutes, then serve warm or at room temperature.

To Store

  • The cake can be stored in an airtight container and store at room temperature for up to 2 days and in the freezer for a month.

Notes

The recipe is adapted from Green Cilantro, originally from Joanne Chang’s Flour.

Nutrition

Serving: 1 9-inch cake · Calories: 3999 kcal · Carbohydrates: 568 g · Protein: 40 g · Fat: 186 g · Saturated Fat: 110 g · Polyunsaturated Fat: 11 g · Monounsaturated Fat: 51 g · Trans Fat: 7 g · Cholesterol: 1350 mg · Sodium: 909 mg · Potassium: 1375 mg · Fiber: 16 g · Sugar: 440 g · Vitamin A: 6736 IU · Vitamin C: 433 mg · Calcium: 561 mg · Iron: 12 mg
Author: Namiko Hirasawa Chen
Course: Dessert
Cuisine: American
Keyword: cake, pineapple
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5 from 2 votes (1 rating without comment)
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Thank you for this recipe this was super delicious! I made the following modifications: for the pineapple, I used frozen pineapple chunks. For the cake, I used three whole eggs and 1 tbsp sugar and beat them until super fluffy. To bake, I baked them in six individual portions in a jumbo muffin tin to make mini cakes. I think next time I will use regular size muffin tins to make the cakes even more mini. I will also reduce the butter in the caramel and maybe make a fluffier cake more like a biscuit. It didn’t take too much time because the caramel took a long time due to the large amount of water in it and I made all the other ingredients while the caramel was boiling. I like this method of using lots of water to make the caramel. It’s much more full proof this way versus melting sugar with no water which is tricky.5 stars

Hi, Cindy! Thank you for experimenting with Nami’s recipe.
We’re pleased to hear your cake turned out well!😃 Small individual cakes sound adorable too. Happy baking!

Hi Nami, Can i replace the pineapples with oranges slices? how do i adjust the ingredients?

Hi Fel, Thank you very much for trying Nami’s recipe.
We have never tried with Orange slice before. But we think you can replace the pineapple amount with orange. You can also adjust the sugar amount for your liking. We hope it helps!