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5 from 1 vote

Gluten Free Poached Pineapple Upside Down Cake

This is an elegant twist on a classic: using homemade vanilla honey poached pineapple!
Prep Time1 hour 30 minutes
Cook Time50 minutes
Resting time1 hour
Course: Breakfast, Dessert
Cuisine: American
Diet: Gluten Free
Keyword: cake, easy, gluten free, honey, pineapple, pineapple cake, poached, upside down cake, vanilla
Servings: 9 people
Calories: 400kcal
Author: Amelia Farber

Equipment

  • Large saucepan
  • 9x9 inch square cake pan or 9 inch round pan

Ingredients

For the poached pineapple:

  • 1 whole ripe pineapple
  • 1 Cup good honey
  • ½ Cup white sugar
  • 1 whole vanilla bean sliced lengthwise - scrape the seeds out and into the pot
  • 1-2 whole star anise
  • ¼ tsp orange zest
  • ½ tsp whole peppercorns
  • 5 cups water

For the cake topping:

  • ½ Cup salted butter
  • Cup packed brown sugar
  • Pinch salt
  • 1 ½ Tbsp honey
  • 1-1 ½ cups poached pineapple patted dry with paper towels

For the cake layers:

  • 2 large eggs
  • ½ Cup packed brown sugar
  • ¼ Cup sour cream
  • Cup pureed poached pineapple in juices add pineapple to a blender and pour in enough poaching liquid to nearly-cover the pineapple
  • 2 tsp vanilla extract
  • 1 Cup gluten free 1-1 flour with xanthan gum added if it doesn't have xanthan gum, add 1/2 teaspoon xanthan gum
  • ½ Cup packed blanched almond flour
  • 1 tsp baking powder
  • ½ tsp baking soda
  • tsp salt
  • ½ Cup browned salted butter melted but cooled

Instructions

For the poached pineapple (takes about 2 hours - you can make this a day in advance!):

  • Combine the water, sugar, star anise, peppercorns, scraped vanilla seeds and the empty vanilla pod, and honey (everything except the pineapple) in a medium saucepan/soup pot and begin heating over medium high heat, stirring constantly until the sugar has dissolved, then continue to cook until the liquid has come to a boil and then cook for 10 minutes. While the liquid is cooking, peel and slice the whole pineapple, remember to slice into thinner pieces about 1/3-1/2 inch thick, 1-2 inches wide in shapes that you like - you'll be arranging them as the topping of the cake! Then add all of the pineapple pieces to the poaching pot, bring back up to a boil and cook for 5 minutes then remove from heat and let the whole pot, pineapple included, cool to room temp (about an hour). You can make this a day in advance and just pour the pineapple and liquid into a large bowl and keep it in the fridge. Save all of the poaching liquid! You’ll use some for the cake and can keep the rest in the fridge for drinks!

For the cake:

  • Preheat the oven to 350° Fahrenheit and grease a 9x9 inch square or a 9 inch round cake pan (either works!) with butter or cooking spray, then set aside. Then make your browned butter so that it can cool before using! In a small saucepan over medium-low heat, melt all of the butter and stir constantly until melted and simmering. Continue to simmer, on medium heat, for at least a few minutes, until the popping and hissing sounds have completely subsided (this is the water in the butter burning off – you’ll know once it’s silent). Continue to cook, stirring constantly, until the butter reaches an amber color and smells nutty or caramelly - it will foam up and the browned milk solids will bubble up. Once it reaches that color, immediately take off the burner and let sit until room temp.
  • Then make your topping. In a small saucepan, heat the ½ cup butter (not the browned butter), ⅓ cup brown sugar, pinch of salt, and 1 ½ Tablespoons of honey over medium-low heat until the butter is bubbling. Whisk constantly until the mixture is homogenized (ie all the butter is combined with the sugar), then pour the mixture into your prepared baking pan and tip the pan so that the mixture covers the bottom evenly to the edges.
  • Then pat dry slices of your poached pineapple and arrange a single layer of pineapple slices on the bottom of the pan on top of the brown sugar butter mixture however you like! Then set aside while you make the cake batter.
  • Make the cake batter! In a large bowl, whisk together the eggs, brown sugar, sour cream, vanilla, and pureed pineapple until smooth. Add in the flour, almond flour, baking powder, baking soda, and salt, and whisk until combined. Then pour in the liquid browned butter (make sure to scrape in all of the little brown bits - those have the flavor!), and whisk until fully combined and smooth. Pour the batter on top of the pineapple topping in the pan and carefully spread to the edges, smoothing the top. Then bake for 35-40 minutes or until a toothpick inserted into the center of the cake comes out clean. Let the cake cool 20-30 minutes before putting a plate over the top of the pan and flipping the entire cake over slowly so that the pineapple isn’t disturbed. Remove pan and voila! Let cool completely before slicing.