Caramelized Pineapple Upside-Down Cake

This is not the pineapple upside-down cake that I used to make back in the day, you know the one with the canned pineapple and maraschino cherries from the Betty Crocker cookbook.  This cake is all grown up with a  vanilla bean scraped into the cake batter and a splash of brandy.  My pineapple upside-down cake is an elegant cake fit for a special dinner party or just for some seriously scrumptious dessert eating, preferably shared with family or friends.  I spent some time doing a little research for an updated version of the recipe and ended up using a combination of ingredients that sounded good to me in all the recipes I found.  The idea of using brandy and a vanilla bean in the batter came from "In The Sweet Kitchen" by Regan Daley.  If you like to bake you should seriously consider adding this cookbook to your collection.  I find myself using this cookbook as a reference for many things I bake as it is full of fabulous recipes for just about any kind of dessert as well as tips on techniques and tons of information on ingredients.  I also went to a cookbook new to my collection, 'Flour' by Joanne Chang for her recipe for old fashioned pineapple upside-down cake as well as 'The Cake Bible', another one of my favorites by Rose Levy Beranbaum.  I decided to leave out the sweet cherries as well as pecan halves and just go with the slices of pineapple in the topping.  Why?  Because that's my favorite part of the cake and I didn't want any of those cherry or pecan halves getting in the way of my caramelized pineapple slices.  I sliced a fresh pineapple into thick slices then simmered them in caramel sauce on top of the stove, that would be good all by itself served on top of vanilla ice cream.  An upside-cake can also be made in a cast iron skillet which saves the step of transferring the caramelized fruit into a cake pan before pouring in the cake batter and placing in the oven.  I like to use a cake pan for this recipe just because it's how I've always done it so I guess I do honor some traditions, for sure the good ones.

Ingredients and Directions for Caramelized Pineapple Upside-Down Cake

1 pineapple

1 3/4 cups sugar, separated 1 cup and 3/4 cup

1/2 cup water
6 tablespoons unsalted butter, cut into pieces, plus 1/2 cup melted and cooled
1 cup all purpose flour
1 teaspoon baking powder
1/4 teaspoon sea salt
2 eggs, at room temperature
3 egg yolks, at room temperature
1/2 vanilla bean, seeds scraped out
2-3 tablespoons brandy, or a very generous splash


Preheat the oven to 350 degrees 
Generously butter a 9 inch cake pan

Slice off the top and bottom of your pineapple so it sits evenly on your cutting board.  Using a heavy knife peel, halve and core the pineapple.  Cut each half of the pineapple in half and then cut into slices 1/2 inch thick.

Put 3/4 cup sugar in the bottom of a heavy medium saucepan.  Add the water, swirl pan to moisten the sugar.
Place the pan over a high heat and bring to a rolling boil.  Don't stir just let it boil until the sugar bubbles all over and starts to turn brown.  This will take 4-5 minutes.  The sugar will turn brown, thicken and turn syrupy.
Carefully swirl the pan to evenly caramelize the sugar.  Lower the heat and carefully whisk in the pieces of butter.  Add the slices of pineapple to the bubbling caramel very carefully!  Simmer the pineapple for about 10 minutes.  Transfer the pineapple slices to the prepared cake pan  arranging in a circular pattern, covering as much of the bottom as possible.

In a medium bowl sift together the flour, baking powder and salt.  In a large bowl whisk together the eggs and egg yolks until very well blended.    Slowly whisk in the sugar, vanilla seeds, generous splash of brandy and melted butter.  Using a large rubber spatula fold the flour mixture into the egg/sugar mixture until combined.

Pour the batter over the pineapple slices in the cake pan, making sure the batter fills in evenly around the slices.  Bake for 45-50 minutes until the top is golden brown and the top of the cake springs back when lightly pressed with a fingertip.

Cool the cake on a wire rack for at least 30 minutes before turning out upside down on a serving plate.  Run a knife along the inside edge of the pan to help separate the cake from the pan.  Place your serving plate on top of the cake and carefully flip upside down.  Lift off the cake pan and continue to let the cake cool before serving.  If a piece of pineapple sticks to the bottom of the pan just replace it back on top of the cake.  The cake is best served the same day you make it, but can be stored for a few days in an airtight container at room temperature.