Gluten Free Poached Pineapple Upside Down Cake with Hungarian Sweet Wine

Pineapple upside down cake has been a life-long love. One of those loves that you don’t often cherish because for some reason it always seems too tricky to make. Well, I’m here to tell you that it’s absolutely not and you should absolutely make this gluten free pineapple upside down cake the very next chance you get. This one was a labor of love, because the lead up to this final recipe was LONG. We’ve been planning our third Wind & Desserts pairing with our friend Iker (check out his awesome knowledge on wine here!), who’s training to be a sommalier in Austria, for weeks now, and we had landed on a Hungarian sweet white wine, Royal Tokaji, as the wine and a pineapple cake as the dessert. Iker mentioned that he always gets a bit of pineapple when tasting Tokaji, and I loved the idea of making a pineapple cake (other than the pineapple + whipped cream cake, and these piña colada cupcakes, we don’t have many pineapple things on the blog). So I drafted an elaborate recipe for a pineapple layer cake, filled with poached pineapple, pineapple pastry cream, and covered in whipped cream. Ah, dreams…

The cake itself, on a first try, turned into a complete disaster: I added way too much liquid and used a bunch of powdered freeze dried pineapple which apparently makes things CRAZY gummy so I ended up with a sort of Dutch baby/mochi/clafoutis/custard mess that deflated and was chewy as heck but tasted magnificent. Second time around, the cake was gorgeous – changed the whole recipe and it was a breeze. But then came constructing. Each ingredient was glorious: homemade poached pineapple – soaked in a mixture of honey, sugar, water, vanilla beans, star anise, and peppercorns (SO dang good – just plain, on ice cream, what have you), the pineapple pastry cream was ABsolutely fantastic (I ate all the extra), and the whipped cream was, well, you can’t go wrong. But I quicly realized, as the cake slid into three different directions and the entire thing self-destructed into a pile of soft fluffy cream/cake/cream/pineapple, that I had mis-judged the structural integrity of all of those incredible components when put together. SO, after lamenting over the ruination of a perfectly good cake, I took a break, re-strategized with Iker, and drafted a BRAND new recipe for a pineapple upside down cake, using the poached pineapple as the keystone ingredient. And here we finally are: one perfect gluten free pineapple upside down cake, a whole lot of pineapple cake/pastry cream eaten in the last twelve hours, and some decent photos. WHEW.

So, here’s to baking fails and the new and improved ideas we get out of them. And here’s to wine!! The wine was absolutely gorgeous – highly recommend finding yourself a bottle (this one was readily available here in California so ask around at your local wine shop or check online!). Looking for other sunny treats? Try these guava cheesecake cupcakes, or this passion fruit tart, or this kiwi lime tart, or this yuzu tart! (we like tarts).

While you’re waiting for this to bake, or just for fun, check out the actual live tasting Iker and I did of both the wine and cake here!

Print Recipe

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 hr 30 minutes mins

Cook Time50 minutes mins

Resting time1 hour hr

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
• 9×9 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
• ⅓ 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
• ⅔ 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
• ⅓ 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 9×9 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.

Tag @sisterssansgluten on Instagram if you snap a photo of your cake!

Food photography and styling by Amelia Farber