Vintage Bourbon Caramel Pineapple Upside-down Cake

I think the first time I ever had Pineapple Upside-down Cake was about 2 years ago for a friends birthday. It wasn’t something that I grew up with, we had lots of spice cakes because that was my dads favorite and his birthday is Christmas day but I dare say that this cake would be something he would like, simple and not too sweet.

Baking fruit in the bottom of cakes has been around since the middle ages but the pineapple upside-down cake first showed up on the scene in the mid-1920’s after the Hawaiian Pineapple Company asked for recipe submissions for creative ways to use their new canned pineapple rings and thus this cake was born.

I like this recipe because it has two interesting ingredients bourbon in the caramel and cardamon in the cake. I hope you get to try your hand at making this soon!

The beginnings of the caramel. I love that there is bourbon in it, I used Makers Mark because that’s what I had on hand but any will do.

I used canned pineapple but fresh is probably better just make sure you dry it.

Pour your bourbon caramel into the bottom of your greased baking pan. Place the pineapple rings around in the caramel and place a cherry in the inside of each ring.

Place the cake batter over the pineapple and caramel evenly. Smooth to make sure that it is all covered.

Note of caution- I covered my cake evenly but I still had caramel sneak up the sides and spill out to the bottom of my oven which if you have ever had the pleasure of burnt caramel scent fill you kitchen you’ll definitely want to place the cake on a piece of foil which can be just tossed after. No need to soak and scrub burnt caramel off a cookie sheet!

Let the cake rest for at least 30 minutes. Place your serving dish over it and quickly flip it right side up.

Bourbon caramel, no words necessary.

The sour cream makes the cake moist and all of the mixing makes it light – best of both worlds.

Taste testing had to be done.

Enjoy!

much love!
jess

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Vintage Bourbon Caramel Pineapple Upside-down Cake

Bourbon Caramel
Nonstick spray
1 1/2 cups brown sugar
1/2 cup (1 stick) unsalted butter, cut into pieces
1/4 cup bourbon

Cake
1 medium pineapple or 1 can of pineapple, sliced
1 1/3 cups cake flour
2 teaspoons baking powder
1 teaspoon kosher salt
1/8 teaspoon ground cardamom
¼ teaspoon of ground cloves
1 cup sugar
1/2 cup (1 stick) unsalted butter, room temperature, cut into 1-inch pieces
2 teaspoons vanilla extract
2 large eggs
1 cup sour cream

You’ll also need:
A 10-inch-diameter cake pan with 2-inch-high sides
1 small jar of maraschino cherries

For the Caramel:
Preheat oven to 350°. Coat cake pan with nonstick spray; set aside. Cook brown sugar and butter in a small deep heavy saucepan over medium heat, whisking occasionally, until mixture is bubbling and sugar is completely dissolved. Boil, whisking occasionally, until caramel darkens, thickens, emulsifies, and pulls away from sides of pan, about 3 minutes.

Remove from heat and whisk in bourbon (mixture will bubble vigorously). Return caramel to a boil; cook for 1 minute. Pour caramel into prepared cake pan and swirl pan until bottom is completely covered. Let cool completely before proceeding (caramel will harden).

For the Cake:
If you are using a fresh pineapple, make sure to cut all the brown eyes off. Also, with both fresh and canned, be sure to dry off the pineapple. Arrange pineapple rings on top of caramel in cake pan without overlapping. Place one cherry in the inside of each of the pineapple rings.

Whisk flour, baking powder, salt, cloves and cardamom in a medium bowl. Beat sugar and butter in another medium bowl until light and fluffy, 5–6 minutes. Add vanilla. Then add eggs one at a time, beating to blend between additions and be sure to scrape down sides of bowl. You’ll want to beat the egg mixture until it has doubled in volume and is very light and fluffy (this should take about 2-3 minutes). Scrape bottom of bowl well, making sure to incorporate all butter into eggs. Beat for 1 minute longer.

Beat in flour mixture in 3 additions, alternating with sour cream in 2 additions, beginning and ending with dry ingredients. Pour batter into pan; smooth top.

Bake cake until a tester inserted into the center comes out clean, 50–60 minutes. Transfer to a wire rack. Be sure to let it cake cool in pan for 30 minutes. Run a sharp knife around sides of pan to loosen cake; tap bottom of pan and invert cake onto a large plate.

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