Recipes Desserts Fruit Desserts Pineapple Dessert Recipes Pineapple Upside-Down Cake from Scratch 4.5 (8) 7 Reviews 7 Photos This pineapple upside-down cake from scratch is an old-fashioned cake recipe from my German grandmother. She used this same cake batter for many different fruits as an alternative to pineapple. She often used fresh Italian prunes or pitted fresh cherries. My grandparents owned a bakery, and this cake was very popular in the 1950s and 1960s. Serve it warm or at room temperature with whipped cream. Submitted by BakerGal Updated on October 8, 2024 Save Rate Print Share Close Add Photo 7 7 7 7 Prep Time: 15 mins Cook Time: 40 mins Additional Time: 15 mins Total Time: 1 hr 10 mins Servings: 10 Yield: 1 (9-inch) cake Jump to Nutrition Facts Cook Mode (Keep screen awake) Ingredients 1x 2x 4x Oops! Something went wrong. Our team is working on it. Original recipe (1X) yields 10 servings ½ cup brown sugar ¼ cup unsalted butter, melted 3 (1/2-inch thick) slices fresh pineapple, quartered 12 frozen cranberries ⅔ cup white sugar ½ cup unsalted butter, softened 2 large eggs 1 ½ teaspoons baking powder 1 teaspoon vanilla extract ½ teaspoon almond extract ½ teaspoon ground cinnamon ¼ teaspoon salt 1 ½ cups unbleached all-purpose flour ¾ cup milk Directions Preheat the oven to 350 degrees F (175 degrees C). Grease a 9x2 1/2-inch round cake pan. Combine brown sugar and 1/4 cup melted butter in a bowl; spread evenly into the prepared pan. Place 10 pineapple pieces around outer edge of pan, facing the same way, place remaining 2 pieces in the center. Place 1 cranberry between each pineapple piece. Beat white sugar and 1/2 cup softened butter together in a bowl with an electric mixer until light and fluffy. Add eggs, one at a time, beating well and scraping sides of the bowl after each addition. Beat in baking powder, vanilla extract, almond extract, cinnamon, and salt until combined. Add flour and milk to batter in 3 additions, adding 1/2 cup flour and 1/4 cup milk at a time, mixing well after each addition, until thoroughly combined. Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula. Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes. Cool cake on a wire rack for 15 to 20 minutes. Run a knife around the edges to loosen. Place a plate over pan and quickly invert to release cake, waiting a few seconds and tapping the pan several times if it doesn't immediately separate from the pan. Cook's Notes: This is a very easy cake to make. A young person could make it with some parental guidance with the pineapple cutting and handling of the hot pan. This cake is not as sickeningly sweet as some pineapple upside-down cakes and not as greasy because less butter and brown sugar are used to prepare the pan. I use frozen cranberries or frozen pitted cherries instead of maraschino cherries, because I don't like the taste or artificial coloring of the maraschino cherries. But something red on the cake makes this one still look traditional. You can use canned sliced pineapple instead of fresh, and vanilla bean paste instead of vanilla extract. I Made It Print Nutrition Facts (per serving) 319 Calories 15g Fat 42g Carbs 4g Protein Show Full Nutrition Label Hide Full Nutrition Label Nutrition Facts Servings Per Recipe 10 Calories 319 % Daily Value * Total Fat 15g 20% Saturated Fat 9g 47% Cholesterol 75mg 25% Sodium 158mg 7% Total Carbohydrate 42g 15% Dietary Fiber 1g 3% Total Sugars 27g Protein 4g 8% Vitamin C 8mg 9% Calcium 87mg 7% Iron 1mg 7% Potassium 102mg 2% * Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs. ** Nutrient information is not available for all ingredients. Amount is based on available nutrient data. (-) Information is not currently available for this nutrient. If you are following a medically restrictive diet, please consult your doctor or registered dietitian before preparing this recipe for personal consumption.