To be honest, I was initially disappointed with this cake. The day I made it -- Valentines' Day, a Thursday -- the topping struck me as too bitter, despite all the caramel encapsulating the pineapple. But by Saturday, the bitterness had given way to a gentle tartness, pairing well with the dense and lovely vanilla-flavored cake. I was snitched away pieces every time I had the chance.
Carmelized Pineapple Upside-Down Cake (from In the Sweet Kitchen)
1 large, sweet ripe pineapple
1/3 c. unsalted butter
1 cup plus 2 Tbsp sugar
1 ½ cups all-purpose flour
1 ½ tsp. baking powder
¼ tsp salt
3 large eggs
4 or 5 large egg yolks (use 5 if the yolks seem small)
1 ½ cups sugar
1 Tbsp Brandy
2 tsp. vanilla
¼ cup butter, melted & cooled
Preheat oven to 350-degrees F. Grease a 10-inch springform cake pan and line the bottom, and 2 inches up the sides, with a sheet of foil. Press the foil into the pan, smoothing out creases as best as possible. Grease the foil and line the bottom with a circle of parchment paper. Grease the paper and sprinkle the bottom with a little sugar, carefully tapping out the excess while keeping a finger on the linings to hold them in place.
Cut the rind from the pineapple and cut away all the tough little eyes. Cut the fruit lengthwise into four pieces, setting aside one quarter for another use. Slice each of the remaining three quarters lengthwise into three pieces, then slice each of these into 1/3- to ½- inch slices. Place these into a bowl and set them within close reach of the stove.
Melt the 1/3 cup of butter in a large, heavy pot over medium heat. As soon as the butter is liquid, add the 1 cup plus 2 Tbsp. of sugar and stir constantly with a wooden spoon until the sugar dissolves and begins to color. At first, the mixture will be grainy and foamy , then after a few minutes, the oil will separate from the caramel and rise to the top. Keep stirring slowly, the mixture should look thick and creamy. Watch carefully, continuing to stir, for the caramel to turn a dark amber color.
As soon as the caramel is this color, place all the pineapple slices in the pot, being careful not to get burned by the splatter. Allow the fruit and caramel to sputter for about 30 seconds, then use the wooden spoon to move the fruit around and become covered by the caramel. The syrup will likely have seized a bit but the lumps will eventually melt back down. . When the contents have settled into a steady boil, keep stirring slowly for about 6 yo 8 minutes until the pineapple is golden with glassy edges. Remove the pot from the stove and set beside the prepared pan.
Using tongs to grab hold of the pineapple, arrange slices decoratively in the pan. Use a slotted spoon to remove any little bits of pineapple still in the caramel, and return the pot to the head. Continue boiling, stirring slowly, until the mixture is very thick and syrupy, being careful not to burn the caramel. You may need to tilt the pan back and forth gently to gauge the consistency – it should be similar to that of thick honey. When ready, pour the caramel over the pineapple slices, and set the pan aside.
Into a small bowl, sift the flour, baking powder, and salt; set aside. In a larger bowl, lightly whisk the eggs and egg yolks to break them up. Whisk in the 1 ½ cups sugar, then blend in the brandy and vanilla. Add the dry ingredients to the egg mixture in two or three additions, stirring with a whisk until thoroughly incorporated. Gently stir in the cooled melted butter; the batter will be a bit runny. Pour the batter over the pineapple slices in the pan, being careful not to disturb the fruit.
Place the cake pan on a baking sheet and set in the middle of the preheated oven. Bake for 70 to 80 minutes. A golden crust should have formed on the top of the cake and the edges should be beginning to pull from the sides of the pan. To test for doneness, poke a wooden skewer into the cake, making the hole a bit larger than the skewer – it should come out clean or with a few moist crumbs. Transfer the pan to a rack and cool for 7 or 8 minutes, then run a thin-bladed knife around the cake and carefully release the sides of the pan.
Invert the cake onto a serving platter and remove the bottom of the pan; peel away the foil and parchment taking care not to disturb the hot cake. Cool completely before serving or covering and storing.
This can be stored for several days at room temperature if it’s well covered.