Pineapple Upside Down Cake Image

Pineapple Upside Down Cake

Origins: Chef's Stories - "Origins: Chef's Stories"

Prep Time
Cook Time


Piloncillo Sauce

  • 3 cups heavy cream
  • 1 cup piloncillo, cut into small pieces
  • ½ cup salted butter/cubed
  • 1/2 orange, zested
  • 1/2 lemon, zested
  • 10 canned pineapple rings
  • 1/2 cup maraschino cherries, drained and minced


  • 2 ½ cups cake flour
  • ½ teaspoon salt
  • ¾ teaspoon baking powder
  • ¼ teaspoon ground cinnamon
  • ¼ teaspoon ground star anise
  • 1 cups granulated sugar
  • ½ cup butter, room temp
  • 3 eggs
  • ¾ cup buttermilk
  • 1 tablespoon vanilla bean paste
  • ¼ cup vegetable oil
  • Pineapple flowers, for garnish
  • Whipped cream, for garnish
  • Cherries, for garnish
  • Chopped walnuts, for garnish


Piloncillo Sauce

  1. Spray a 9x13 glass, oven-safe pan with non-stick baking spray and line with parchment.
  2. In a medium saucepan add heavy cream, piloncillo pieces, butter and the zest of the orange and lemon. Bring to a boil and allow to simmer for 15-20 minutes. Pour into a 9x13 pan. Let the sauce cool, then place a layer of pineapple rounds and maraschino cherries.


  1. Preheat the oven to 350 degrees.
  2. In a medium size bowl whisk together the flour, salt, cinnamon, star anise, and baking powder. Set aside.
  3. Place the butter and sugar in the bowl of a stand mixer. Using the paddle attachment beat on medium speed for 2 minutes. In a separate bowl whisk together the eggs, vanilla bean, and buttermilk. Add the egg and buttermilk mixture to the butter and sugar and mix until incorporated. Then add the dry ingredients.
  4. Pour the cake batter into your 9x13 pan, covering the pineapples, cherries and piloncillo sauce. Lightly tap the cake pan on the counter and place in the oven for 25-26 minutes.
  5. Allow the cake to cool, then flip it upside down to remove it from the pan. Cut into squares and garnish as desired.