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Pineapple Upside-Down Cake is one of the most iconic desserts around. Which is one reason why I just had to make a gluten free Pineapple Upside-Down Cake a delicious reality.
The tradition of baking a cake with fruit on the bottom, which is then flipped onto a pan, dates back to early cast iron cooking over an open flame. But the first record of the ultimate fruit-on-the-bottom-flipped-upside-down cake — Pineapple Upside-Down Cake — is traced back only to the early 1920s.
An engineer employed by James Dole (of Dole canned pineapple fame) invented a pineapple slicing machine in 1911 and thus began the mass production of the perfectly round, lovely rings we all associate with this famous flipped cake, punctuated by bright red maraschino cherries, of course.
For my gluten free Pineapple Upside-Down Cake, I diverted a bit from the typical. One reason is that I had fresh pineapple and fresh is always best. I also happened at the market upon some delicious organic Rainier cherries (is there anything better than fresh-picked cherries?!).
The taste produced by the happy marriage of these two fresh fruits is nothing short of delightful. I promise you that you will notice a difference when you skip the canned rings and sickeningly sweet maraschinos (for more reasons to avoid these high fructose corn syrup, Red Dye #4 soaked candied cherries, go here). Promise.
The resulting cake (or individual cakes) beckon with gorgeously natural pineapple rings, real cherries and a flavorful crumb that could only come from homemade. Arrange your fruits in any pattern you like — don’t feel bound by conventional rounds or perfectly spaced berries. Make it your own. Make it beautiful.
Whether you buy or make your own almond or gluten-free oat flour, using one of those flours in addition to the base of my gfJules Gluten Free All Purpose Flour makes this recipe healthier while adding a subtle, something extra to the flavor that I think you’ll really like. No oils in this recipe, either. You’re welcome.
Bake in individual ramekins or one large round or rectangle — remember, it’s your own creation. And you won’t know just how lovely it is until after it’s baked and flipped, but the surprise will be worth it. I’d love to see your version, so drop me a line or leave a comment below; you may just provide inspiration for someone else’s Pineapple Upside-Down Cake!
Preheat oven to 350° F (static) or 325° F (convection).
Lightly oil, then sprinkle the bottoms of one 9 –inch round cake pan or 4 small ramekins with 3-4 tablespoons brown sugar.
Arrange pineapple rings to cover the bottoms of the pans and insert cherries into the centers of the rings or between rings in any decorative pattern. Set aside.
In a large bowl, whisk together all dry ingredients including 1 cup brown sugar, then set aside.
Cut two other pineapple rings into chunks, then purée in a blender or food processor. Remove 2 tablespoons of liquid and set aside. (Use any leftovers in a smoothie or fruity cocktail!)
In a large mixing bowl, beat the eggs until light, approximately 3 minutes.
Add the cream cheese, yogurt, pineapple juice and vanilla extract, mixing until well blended. Slowly add the dry ingredients, mixing an additional 2 minutes after all ingredients are combined. The batter will be smooth, but thin.
Pour the batter into the prepared cake pan(s), completely covering the pineapple rings and sugar.
Bake for 40-45 minutes for 9-inch pan or 30 minutes for small ramekins. Test with a toothpick or cake tester before removing from oven – continue cooking until tester inserted into the cakes comes out clean or with dry crumbs attached.
If the cake has mounded in the center during baking, lay a large knife on the top of the cake pan and saw gently across to evenly cut the bottom of the cake so it sits flat once inverted.
Invert cake(s) onto plates to cool (loosen with a butter knife around the edges) until the cakes drop.
Serve warm or cold.
I hope you love this recipe as much as we do!
Pin it for later!