Vintage Pineapple Upside Down Cake

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I am starting a vintage recipe series, and this is my first! This old time classic is absolutely delicious and you won’t believe it only requires a box of cake mix, can of pineapple slices, brown sugar, butter, and maraschino cherries! And, of course, the oil and eggs called on the back of the box! But, in place of the water we are using the pineapple juice from the can! Oh my GOODNESS! This cake was literally my favorite I have ever made. Ans, before you think that how can a cake with a box of cake mix be vintage…the first cake mixes were introduced in the 1930s! We know the moms in the good old days did a ton of work, so a box of cake mix must have been a blessing! Let’s make it!

Vintage Pineapple upside down cake
A woman in a white top and jeans smiles while holding a plate with a pineapple upside-down cake in a modern kitchen.

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Pineapple, upside down cake! #VintageRecipes #PineappleUpside downCake Mother’sDayRecipes

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A pineapple upside-down bundt cake topped with pineapple rings and red maraschino cherries, displayed on a white plate over a yellow cloth with red cherry patterns.
Melissa Jo

Vintage Pineapple Upside Down Cake

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Ingredients
  

  • 1 box of yellow cake mix
  • and the 3 eggs. 1/2 cup of oil called for on the back of the box
  • pineapple juice from canned slices instead of the 1 cup of water called for on the back of the box we will replace that with the pineapple juice from the can. I only had enough with the 15.25 oz. can I bought to fill half a cup of pineapple juice, so I filed the other half with water. AND IT WAS AMAZING! But, buy the 20 oz. can so you can have all pineapple juice.
  • 1/2 cup of melted butter I used slated butter so, 1 stick of butter
  • 1/2 cup of brown sugar
  • 20 oz. can of pineapple slices packed in 100% juice
  • 6-7 marachino cherries
  • Pam or butter to grease the bundt pan. use A LOT

Method
 

  1. Preheat your oven to 350°F (180°C).
  2. In a mixing bowl, prepare the cake mix according to package directions, substituting the reserved pineapple juice for an equal amount of water.
  3. In a separate bowl, mix the melted butter and brown sugar together.
  4. Pour the butter and brown sugar mixture evenly into the bottom of a greased bundt pan.
  5. Arrange the pineapple slices in a single layer over the butter and brown sugar mixture.
  6. Place one cherry half in the center of each pineapple slice.
  7. Pour the cake batter evenly over the pineapple slices.
  8. Bake for 40-45 minutes, or until a toothpick inserted into the center of the cake comes out clean.
  9. Remove the cake from the oven and let it cool for 5 minutes.
  10. Invert the bundt pan onto a serving platter and let the cake cool completely.
  11. Serve and enjoy!

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Notes

  • Buy a can of pineapple slices packed in 100% juice not heavy syrup. You will use the juice from the can in the recipe in place of water.

  • I bought a 15.25 oz. can of pineapple slices in juice, and it wasn’t enough juice to make 1 cup. I used water for the other 1/2 cup. and it was DELICIOUS! But, it would be even better if you got the 20. 0z. can of pineapples packed in juice so you could use the whole cup of pineapple juice in place of water.

  • I used a bundt pan in this recipe and it turned out so beautiful!

 

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