Vanilla Pineapple Upside-Down Cake

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Vanilla Pineapple Upside-Down Cake

This Vanilla Pineapple Upside-Down Cake is a twist on the traditional. The classic American pineapple upside-down cake gets a luscious revamp with our test kitchen’s go-to vanilla: Heilala Vanilla. Heilala’s premium vanilla extract brings sweetness and complexity to the buttery cake base of our Pineapple Upside-Down Cake. The star of this recipe, our showstopping pineapple top, gets deep caramelized notes from fresh pineapples cooked with Heilala’s vanilla syrup and vanilla paste. Striking the perfect balance between the pineapple’s tartness and Heilala’s sweetness, this is the dessert your summer soirées have been waiting for.

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3.0 from 2 reviews
Heilala Vanilla Pineapple Upside-Down Cake
Makes 1 (9-inch) cake
  • ¼ cup (75 grams) Heilala Vanilla Syrup
  • 3 tablespoons (42 grams) unsalted butter, melted
  • 2 tablespoons (36 grams) Heilala Pure Vanilla Bean Paste, divided
  • ½ cup (110 grams) firmly packed dark brown sugar
  • 1 large pineapple (1,662 grams), cleaned, cored, and thinly sliced lengthwise
  • ½ cup (113 grams) unsalted butter, softened
  • 1 cup (200 grams) granulated sugar
  • 2 large eggs (100 grams), room temperature
  • 1 tablespoon (13 grams) Heilala Pure Vanilla Extract
  • 1½ cups (188 grams) all-purpose flour
  • 1½ teaspoons (7.5 grams) baking powder
  • ½ teaspoon (1.5 grams) kosher salt
  • ¼ teaspoon (1.25 grams) baking soda
  • ⅔ cup (160 grams) whole buttermilk
  1. Preheat oven to 350°F (180°C). Butter the sides of a 9-inch enamel-coated cast iron pan.
  2. In a small bowl, whisk together vanilla syrup, melted butter, and ½ tablespoon (9 grams) vanilla bean paste. Pour mixture into prepared dish. Sprinkle with brown sugar.
  3. Starting with outer edge of dish, arrange pineapple slices, curved sides against side of dish, over brown sugar mixture. Work your way toward center (with all pineapple slices facing the same way and slightly overlapping) until bottom of dish is completely covered.
  4. In the bowl of a stand mixer fitted with the paddle attachment, beat softened butter and granulated sugar at medium speed until fluffy, 3 to 4 minutes, stopping to scrape sides of bowl. Add eggs, one at a time, beating well after each addition. Beat in vanilla extract and remaining 1½ tablespoons (27 grams) vanilla bean paste.
  5. In a medium bowl, whisk together flour, baking powder, salt, and baking soda. With mixer on low speed, gradually add flour mixture to butter mixture alternately with buttermilk, beginning and ending with flour mixture, beating just until combined after each addition. Pour batter over pineapple, smoothing top with an offset spatula.
  6. Bake until a wooden pick inserted in center comes out clean, 45 to 50 minutes. Let cool in pan for 10 minutes. Run a knife around edges of dish to release sides of cake, if necessary. Carefully invert cake onto a flat serving plate. Serve warm or at room temperature.


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  1. I was really excited about this recipe. I went and ordered all of the Heilala products it called for. I followed the recipe instructions meticulously. I baked it for 50 min, let it cool for 10 min and then inverted it. It basically just collapsed into a pool of syrupy liquid. The cake had the texture of a pudding. I don’t know what went wrong. What a waste of the $50 in Heilala products I bought.

    • Hi Zoe! We’re so sorry this recipe did not turn out well for you. There could be several reasons it did not work. Depending on the pan you used, the bake time could vary from what we specified in our recipe. We used an enamel-coated skillet, but if you used a thicker skillet it would take longer to bake. You’ll also want to make sure that the pineapples you’re using are still firm and not overly ripe. An overripe pineapple will release more moisture into the batter than a firm, just-ripe pineapple would. Finally, check for doneness. A toothpick inserted in the center should come out clean, or you can temp the cake. If your thermometer reads 205 degrees, the cake is done. We hope this helps!

  2. After attempting the cake a second time with no success, I tweaked this recipe a bit and it turned out beautifully. Instead of an enamel coated pan I used a cake pan. I used a bit less pineapple than the recipe called for and cut it into thinner slices. Also, I made a caramel with the brown sugar, butter, and the vanilla syrup and poured it into the bottom of my cake pan, instead of just melting butter and throwing brown sugar onto it like the recipe called for. With those modifications it turned out beautifully.


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