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Makeover Pineapple Upside-Down Cake

Both of my boys loved this makeover version of a family favorite, and even my husband, who is a bit picky, wants a piece in his lunch tomorrow! —Mary Lou Moeller, Wooster, Ohio
  • Total Time
    Prep: 15 min. Bake: 35 min.
  • Makes
    9 servings


  • 3 tablespoons butter, melted
  • 1/3 cup packed brown sugar
  • 9 canned unsweetened pineapple slices
  • 9 maraschino cherries halves
  • 2/3 cup sugar
  • 2/3 cup fat-free milk
  • 3 tablespoons canola oil
  • 1 large egg, room temperature
  • 1 teaspoon lemon extract
  • 1/2 teaspoon vanilla extract
  • 1-1/3 cups cake flour
  • 1-1/4 teaspoons baking powder
  • 1/4 teaspoon salt


  • Pour butter into a 9-in. square baking pan; sprinkle with brown sugar. Arrange pineapple slices in a single layer in pan; place cherry halves in center of pineapple slices; set aside.
  • In a large bowl, beat the sugar, milk, oil, egg and extracts until well blended. Combine the flour, baking powder and salt; gradually beat into sugar mixture until blended. Pour into prepared pan.
  • Bake at 350° for 35-40 minutes or until a toothpick comes out clean. Immediately invert onto a serving plate. Serve warm.
Nutrition Facts
1 piece: 288 calories, 9g fat (3g saturated fat), 34mg cholesterol, 172mg sodium, 49g carbohydrate (32g sugars, 1g fiber), 3g protein.

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Average Rating:
  • rena 55
    Dec 12, 2018

    Very tasty, Will make this again.

  • EAW9414
    Mar 26, 2016

    me and my husband loved this recipe I used 2pecet milk and fresh pineapple andused a cast iron skillet it came out perfect but next time all bake it at a less time I havea convention oven and its baking time is fast thanks for the recipe.

  • lbroadh2o
    Apr 20, 2014

    The cake appeared to be cooked at 40 minutes. The cake tester came out clean. Overnight the cake became very soggy .

  • SassyLacey
    Jun 9, 2013

    I loved this recipe and used the crushed pineapple topping as suggested, but the cake was a little dry. I added some pineapple juice drained from the pineapple to the batter but it was still dry. Will add a all of it next time. I also added chopped pecans on the top and they cooked down into the cake and added a delightful addition to this cake. My husband loved it even though it was a bit dry.

  • cynthe66
    May 7, 2012

    The way I do it is I saute some butter, brown sugar and crushed pineapple till browned then spread in the bottom of the pan and continue with the rest of the recipe. I omit the cherries because hubby doesn't like them.

  • ifish3
    Apr 15, 2012

    No comment left

  • karen curnes
    Apr 5, 2012

    I've made this recipe several times. The whole family loves it and it comes out perfect every time.

  • EmilyR369
    Feb 5, 2012

    No comment left

  • apeq29
    Aug 6, 2011

    No comment left

  • bjh173rd
    Apr 26, 2011

    I made this for our Easter dessert. I did not have lemon extract but substituted coconut extract. It was quite tasty.