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The idea of cooking a cake upside down is an old technique that started in the middle ages when cakes were cooked in cast iron skillets. It was easy for the cook to add fruit and sugar in the bottom of the pan and a simple cake batter on top and put it over the fire to cook. Flipping it over onto a plate was a natural way to show the pretty fruit and to let the hot glaze run into the cake as well. The idea of using pineapple dates to soon after 1911 when James Dole of the Hawaiian Pineapple Company had both a machine to cut his pineapples into nice rings and the ability to can them as well. One of the earliest printed recipes for pineapple upside down cake is from a 1924 Seattle fundraising cookbook. The later invention of the maraschino cherry added the necessary color needed to make this cake visually appealing.
- 1 (20 ounce) can pineapple slices, drained
- 1⁄4 cup unsalted butter
- 2 tablespoons maple syrup
- 1 cup light brown sugar
- 9 maraschino cherries, stems removed
- 12 pecan halves (optional)
- 1⁄2 cup unsalted butter, room temperature
- 2⁄3 cup sugar
- 2 large eggs, room temperature
- 2⁄3 cup buttermilk, room temperature
- 1 tablespoon molasses
- 1 teaspoon vanilla extract
- 1 1⁄2 cups all-purpose flour
- 1 teaspoon baking powder
- 1⁄2 teaspoon baking soda
- 1⁄2 teaspoon salt
- 1⁄2 teaspoon cinnamon
- Line a dinner plate with paper towels. Lay the pineapple slices on the plate and blot them dry on both sides. Set aside.
- Lightly butter a 9 inch square baking pan. Combine the butter and maple syrup in a small saucepan over medium heat. When the butter melts, stir in the brown sugar.
- Bring to a slow boil and cook 30 seconds, stirring. Pour the mixture into the buttered pan. Tilt the pan to spread the mixture around.
- Lay the pineapple slices in three rows and put a cherry in the center of each ring. Press one pecan half, if using, in each gap between pineapple slices. Set aside.
- NOTE: If using a round skillet, heat the butter-maple syrup-brown sugar mixture right in the pan. Make a ring of pineapple slices, just touching, with one in the center and proceed with the cherries and pecans.
- To start the cake portion, preheat oven to 350 degrees F.
- Using an electric mixer on medium high, cream the butter, gradually adding sugar. Add the eggs, one at a time, beating well after each addition.
- Beat in 1/3 cup of buttermilk, the molasses and the vanilla.
- Sift the flour, baking powder, baking soda, salt and cinnamon into a bowl. Add half of the dry ingredients to the creamed mixture and beat until smooth. Add the remaining buttermilk, beat to blend then add the remaining dry ingredients and beat to combine.
- Scrape the batter over the pineapple slices and smooth with a spoon or spatula.
- Bake on the center oven rack for 35-40 minutes, until the center of the cake springs back when touched. Put a platter or baking sheet over the pan and carefully invert the cake onto the platter or baking pan. Remove the pan. Wear long sleeves and oven mitts incase the hot glaze leaks out during inversion.
- Cool for at least 10 minutes before serving.