Pineapple upside down cake

February 24, 2010 at 11:47 pm (Cake, Derek's faves, Dessert, Mom’s recipes)

When I was a kid my mom used to make pineapple upside down cake quite frequently.  It was one of my brother’s favorite desserts, and he often asked for it for his birthday.  My mom made the cake in her cast iron pan, which fit exactly 6 pineapple rings around the circumference.  It was perfect, since we had 6 people in my family.  There was also one ring of pineapple in the center of the skillet–that ring always went to the birthday boy (or girl).  This recipe makes a short, fluffy cake with a hint of pineapple flavor.  But the cake is really just a carrier for  the real highlight–the caramelized pineapple rings and ooey-gooey butter/brown sugar mixture.  My mom made a vegan version of pineapple upside down cake, but below I’ve written up the non-vegan version.  Use your favorite egg and butter replacements to make it vegan.

Preheat the oven to 350 F.

Open, drain, and save the liquid from:

  • 1 can pineapple rings, packed in their own juice

Melt in a cast iron pan:

  • 1/4 cup butter

Add, and stir until melted:

  • 3/4 cup brown sugar
  • 1 tsp. vanilla

Arrange pineapple slices around the circumference of the pan, and place one ring in the center.
In a bowl, mix together:

  • 1 cup flour
  • 3/4 cup sugar
  • 1 1/2 tsp. baking powder
  • 1/2 tsp. salt

Make a well in the center for the wet ingredients.  Add and beat for 2 minutes:

  • 1/4 cup oil
  • 1/2 cup + 2 Tbl. pineapple juice (drained from the can)
  • 1 tsp. vanilla
  • 1 egg

Pour batter evenly over the pineapple rings.  Bake 40-45 minutes at 350. When it’s done let it sit for 5 minutes.  Go around the edge of the cake with a knife, then quickly invert the cake directly onto a plate.  Where oven mitts, so you don’t get burned!

This recipe makes a very sweet cake.  The caramelized top is so sweet, I’d like to make the cake less sweet.  I’d like to try the recipe with 2/3 cup sugar, but I’d probably have to reduce the liquid a bit as well.

For comparison, here’s the Cook’s Illustrated ingredients:

Pineapple Topping

  • 1 medium fresh pineapple (about 4 pounds), prepared according to illustrations below (about 4 cups prepared fruit)
  • 1 cup firmly packed light brown sugar (7 ounces)
  • 3 tablespoons unsalted butter
  • 1/2 teaspoon vanilla extract


  • 1 1/2 cups unbleached all-purpose flour (7 1/2 ounces)
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon table salt
  • 8 tablespoons unsalted butter (1 stick), softened but still cool
  • 3/4 cup granulated sugar (5 1/4 ounces)
  • 1 teaspoon vanilla extract
  • 2 large eggs at room temperature
  • 1 egg white at room temperature
  • 1/3 cup whole milk at room temperature

1 Comment

  1. austingardener said,

    I would like to try this recipe with fresh pineapple. thanks for the suggestion.
    I get the cake out of the pan not by going around the pan with a knife, but by kind of shaking the pan to loosen the cake and then inverting.

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