Pineapple Upside-Down Cake

Say aloha to a family favorite. Naturally sweetened with monk fruit, this clean pineapple upside down cake is the perfect clean treat.

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See Also Cooking with Monk Fruit Sweetener




  • 15 Medjool dates, pitted
  • ¼ cup organic, unsalted butter
  • 1 tsp pure vanilla extract
  • 1/4 tsp monk fruit sweetener (TRY: NOW Real Food Organic Liquid Monk Fruit)


  • ½ cup organic, unsalted butter, room temperature + additional for greasing pan
  • 1 15-oz can unsweetened sliced pineapple or 1 whole fresh pineapple, peeled, cored and sliced
  • 2 cups blanched almond flour
  • ½ cup coconut flour
  • ¼ cup arrowroot
  • 2 tsp baking powder
  • 1 tsp ground cinnamon 
  • 1 tsp ground ginger
  • ¼ tsp ground allspice
  • 2 large eggs
  • 3/4 cup whole milk
  • 1 tsp pure vanilla extract
  • ½ tsp monk fruit sweetener (TRY: NOW Real Food Organic Liquid Monk Fruit)


1. Make caramel: In a small bowl, soak dates in ½ cup hot water for 5 minutes. In a blender, place dates and water and purée until smooth. In a small saucepan on high, cook butter until melted, bubbly and brown, 3 to 4 minutes. Remove from heat and whisk in date purée. Cook on medium until fully incorporated, stirring occasionally. Stir in vanilla and monk fruit sweetener.

2. Prepare cake: Preheat oven to 350°F and grease an 8-inch springform cake pan. Line pan with parchment then grease parchment with extra butter. Arrange slices of pineapple on bottom of prepared pan. Pour caramel over pineapple.

3. In a large bowl, whisk together almond flour, coconut flour, arrowroot, baking powder, cinnamon, ginger and allspice. In the bowl of a stand mixer, beat remaining ½ cup butter on high until light and fluffy, 2 minutes. Beat 1 egg into the butter at a time, 1 minute each. Add flour mixture to butter mixture and mix until combined. Add milk, vanilla and monk fruit sweetener and mix until combined. Spread batter evenly over pineapple. Bake for 40 minutes, or until a cake tester comes out clean. Invert cake onto a serving plate immediately to prevent the caramel from sticking.

Nutrition Information

  • Serving Size 1/8 of recipe
  • Calories 531
  • Carbohydrate Content 49 g
  • Cholesterol Content 96 mg
  • Fat Content 36 g
  • Fiber Content 9 g
  • Protein Content 10 g
  • Saturated Fat Content 14 g
  • Sodium Content 189 mg
  • Sugar Content 33 g
  • Monounsaturated Fat Content 15 g
  • Polyunsaturated Fat Content 4 g