Heilala Vanilla Pineapple Upside-Down Cake

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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.

Before you bake, stock up on Heilala Vanilla with an exclusive discount code to Heilala’s Amazon store! Use code BAKEFS07 at checkout to get 20% off your vanilla purchase. Code valid until July 31, 2019.

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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