Monday, January 28, 2013

Pineapple Upside Down Cupcakes

I don't want to bake professionally, but I get asked quite a bit to make certain things. A coworker is having a 1920's themed event in a few weeks and wanted to serve a 1920's dessert. Pineapple upside down cake originated in 1925, so these cupcakes will be absolutely perfect!

I had never made a pineapple upside down cake before and hadn't eaten one in years, so I wasn't really sure what to expect with these. My expectations were exceeded about a thousand times. These were absolutely amazing, and Graham said it was the best pineapple upside down cake he had ever had.

Typically this cake is made with a ring of pineapple & a cherry baked with the cake. I don't like cherries, so I decided to make it a garnish instead of part of the cake. Also, this cake doesn't come with a frosting of any sort. I personally don't think something can be called a cake without a fluffy topping. I made a super fast & easy whipped cream frosting that was absolutely incredible on these (and out of the bowl with a spoon). I had never made homemade whipped cream before, and now I have no idea why people use whipped cream in a can or Cool Whip. It is SO easy to make it from scratch and is so delicious.

I can't wait to make these again, and I hope my coworker & her guests love these as much as we did.

Pineapple Upside Down Cupcakes 
Makes 12 cupcakes
(Recipe adapted from this one.)

  • 1 20 oz can of pineapple chunks (reserve the juice) 
  • 1/3 cup packed light brown sugar  
  • 1/3 cup unsalted butter, melted
  • 1 cup all-purpose flour
  • 3/4 cup sugar
  • 1/2 teaspoons baking powder
  • 1/2 stick unsalted butter, at room temperature
  • 1/2 cup pineapple juice
  • 1 egg  
  • 1 t. of coconut extract
  • 12 Maraschino cherries
  • Whipped cream frosting (recipe to follow)

  1. Preheat the oven to 350°F. Spray or grease a nonstick muffin pan. 
  2.  Drain the pineapple chunks, reserving 1/2 cup juice for the batter. 
  3. Place the pineapple on a 2-3 sheets of paper towels to drain completely.
  4. Melt butter in a small sauce pan or microwave safe bowl.
  5. Mix together the brown sugar and melted butter. Divide evenly among the muffin pan cups (about 1 T. per cup).
  6. Arrange the pineapple chunks on top of the sugar mixture (about 4 per cup). Set aside. 
  7. In the bowl of a mixer, or a large mixing bowl if using a hand mixer, combine the flour, sugar, and baking powder. Mix in the butter and pineapple juice, beating for 2 minutes or until smooth.
  8. Beat in the egg & the coconut extract.
  9. Spoon the batter over the fruit in the muffin pan. 
  10. Bake on the middle rack for 30 minutes, or until a cake tester or toothpick inserted into the center of a cupcake comes out clean.
  11. Cool the cupcakes in the pan for 5 minutes, then place a wire rack on top of the muffin pan and flip the pan over so the pineapple is on top. Let cool completely before topping with whipped cream.

Whipped Cream Frosting
(Recipe modified from this one.)

  • 1/2 pint of heavy whipping cream
  • 1/2 cup of powdered sugar

  1. In a large mixing bowl (or bowl of a stand mixer) beat whipping cream with a whisk or whisk attachment until stiff peaks form.
  2. Mix in the powdered sugar.

Pipe the whipped cream onto cupcakes & top with a cherry. Enjoy!


  1. Hi! Found your blog through #healthySELF - I LOOOVE these cupcakes! Pineapple upside down cake is such an indulging pleasure for me - I like that these are single servings, so hopefully I won't go too crazy next time :)

    1. Thank you for your comment! Good luck not going crazy. If you make these let me know how they turn out! =)


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