Pineapple Upside-Down Cupcakes with Whipped Coconut Cream


For as long as I can remember, I’ve loved tropical-flavored sweet things.

Pina coladas, caramelized bananas on pancakes, coconut milk smoothies, pineapple upside-down cake – I adore them all, especially in the warm weather months.

So I’ve concocted a healthier cupcake version of pineapple upside-down cake, topped off with a yummy whipped coconut cream.


Even Meat-and-Potatoes-Guy, who isn’t so obsessed with tropical-flavored sweets, is almost as addicted to these cupcakes as I am.




Here is everything you’ll need to get started.


First things first:

As soon as you purchase the coconut milk (regular coconut milk should be used for this recipe, not light coconut milk) immediately place it in the refrigerator.

Overnight, all of the coconut fruit – the thick cream – will rise to the top of the can.

The water that has been added to the coconut milk will sink to the bottom.

This will be important for later on.


When you’re ready to prepare the cupcakes, heat the oven to 350 degrees F.

Sift together the following dry ingredients: whole wheat flour, all-purpose flour, baking soda, baking powder, and salt.


Grab a second bowl and mix together: two eggs, some canola oil, some plain nonfat Greek yogurt, some granulated sugar, and a bit of vanilla extract.


Add the flour mixture to the yogurt mixture and stir until everything is well combined.


Then spoon some of the mixture into a muffin pan filled with cupcake liners.

Fill each liner about halfway and no more.

The cupcakes more than double in size during baking, and they’ll overflow if you fill them too high.


While they bake, prepare the pineapple.

Pineapple is the key sweet component in these cakes, but it also makes this dessert more nutrient-packed.

Pineapple is very high in Vitamin C (for a strong immune system), manganese (to maintain strong bones), and beta carotene (to maintain healthy eyesight).

Any kind of pineapple – canned, frozen, or fresh – will work.

For these photos, I used canned pineapple slices to mimic the design of the classic pineapple-upside down cake.

Cut the pineapple into bite-sized pieces (I cut each ring into about six pieces).


Heat just a bit of canola oil in a sauté pan over medium-high heat and add the pineapple along with some 100 percent pure maple syrup.

Then cook and stir until the pineapple becomes golden and caramelized.


To keep the caramelized pineapple from sticking to the pan as it cools, immediately pour the pineapple onto a plate.


When the cupcakes and pineapple are cool enough to handle, cover the top of each cupcake with several pieces of caramelized pineapple.


The caramelized maple should make the pineapple sticky enough to cling to the cupcakes and stay put.

You can also slice off the very top of each cupcake, creating a completely flat surface to arrange the pineapple.


Last step:

Grab the can of coconut milk from the fridge.

Scoop out just the top layer, the coconut  cream. It should be very rich and thick.

Refrigerate the remaining coconut-flavored water to use in another recipe.

Need some ideas? I just so happen to have several (because I just so happen to be addicted to coconut milk!):



Add some sugar and, using a hand mixer set to low speed, whip the mixture until a thick, frothy cream is formed.

It looks delish and it is absolutely heavenly.


I use just a small amount of sugar in the coconut cream recipe, because the cupcakes are already quite sweet. And the coconut cream is so rich, it doesn’t need a lot of sweetness.

I recommend starting with the amount of sugar called for in the recipe and adding about a tablespoon at a time until you reach the sweetness level you prefer.


Top each cupcake with a dollop of coconut cream, and serve.


The decadent-tasting, moist vanilla cake is so perfectly yummy with the sweet caramelized pineapple.

The coconut cream adds another layer of tropical flavor – it’s light, frothy, and very rich tasting.


These treats are an indulgent little escape to paradise, in cupcake form.

Naturally, at least at my house, they have a knack for disappearing very quickly.

Here is the complete, printable recipe:

Pineapple Upside Down Cupcakes with Whipped Coconut Cream
Nutrition Information
  • Serving size: 12
  • Calories: 258
  • Fat: 13.5g
  • Saturated fat: 3.8g
  • Trans fat: 0g
  • Carbohydrates: 32.1g
  • Sugar: 22g
  • Sodium: 172mg
  • Fiber: 1.2g
  • Protein: 3.6g
  • Cholesterol: 28mg
Recipe type: Healthier Desserts
Total Time: 40 minutes
Prep: 20 minutes
Cook: 20 minutes
Yield: 12 cupcakes
  • ½ cup whole wheat flour
  • ½ cup all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • ¼ teaspoon salt
  • ½ cup plus 1 teaspoon canola oil
  • ⅔ cup plus 2 tablespoons granulated sugar
  • 2 eggs
  • ½ cup plain nonfat Greek yogurt
  • 2 teaspoons vanilla extract
  • 1 20-ounce can pineapple slices, each ring cut into six bite-sized pieces
  • 3 tablespoons 100% pure maple syrup
  • ⅔ cup coconut cream from 1 14-ounce can coconut milk (the thick, top layer of cream that is formed when a can of coconut milk is refrigerated for 2-3 hours)
Note: the night before preparing this recipe, refrigerate the can of coconut milk. The thick, creamy layer that rises to the top of the can is required for this recipe.
  1. Preheat the oven to 350 degrees F.
  2. In a mixing bowl, sift together the dry ingredients: whole wheat flour, all-purpose flour, baking powder, baking soda, and salt.
  3. In a separate large mixing bowl whisk the following until well combined: ½ cup canola oil, ⅔ cup granulated sugar, eggs, yogurt, and vanilla extract.
  4. Add the flour mixture to the yogurt mixture and stir just until ingredients are combined.
  5. Fill a muffin pan with cupcake liners and spoon batter into liners, filling each about halfway. Bake for 14-17 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Allow cupcakes to cool.
  6. Meanwhile, heat 1 teaspoon canola oil in a sauté pan over medium-high heat. Add the pineapple and maple syrup and cook and stir until pineapple becomes golden and caramelized. Immediately transfer caramelized pineapple to a plate to cool. Arrange several piece of pineapple over the top of each cupcake.
  7. Remove coconut milk from the fridge and scoop out the thick, cream-like top layer. Add 2 tablespoons granulated sugar and use a hand mixer set to low speed to beat the mixture about 2 minutes, or until a rich, thick cream is formed. (Add additional sugar according to personal taste).
  8. Top each cupcake with a spoonful of coconut cream.
To Store: Cupcakes should be stored at room temperature in an airtight container in a cool, dry, shaded location. Coconut cream should be stored separately in an airtight container in the fridge. Top cupcakes with cream immediately before serving.



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  1. August 1, 2013 / 12:13 pm

    dear god… I need to make these immediately!!! Thanks for this share and the extra 10 pounds that I’ll put on from consuming a whole pan of these…
    Check out my blog too if you get a chance!

  2. August 1, 2013 / 5:24 pm

    I love tropical flavors too and the whipped coconut cream makes a perfect topping!

  3. August 2, 2013 / 1:51 am

    Those cupcakes look absolutely gorgeous! Coconut whipped cream would taste divine! Loved it 🙂

  4. August 2, 2013 / 9:14 am

    Mmh, these little cakes look so tempting and cute.
    Love the icing with coconut cream!

  5. August 2, 2013 / 10:06 am

    First of all, I don’t like pineapple, but yours cooked with maple syrup makes me totally forget that and want to dive in! Second, upside down cupcakes have been on my list for months! These look awesome, and I love the healthy ingredients as always! 🙂

  6. August 2, 2013 / 7:52 pm

    These cakes are amazing, they are right down my street and I will be sure to try them well the sun is still shining. I am as addicted to coconut cream as much as you so I massively appreciate your recipes, they are great. I am lucky enough to chef in the only Thai restaurant in London with a coconut press (The Begging Bowl). We get through 2 sacks a day, which are freshly cracked and peeled, the coconut is then blitzed with hot water then pressed and filtered using the coconu press machine. The coconut is then put in the fridge in order to aid the superstition process. Traditionally in Thai culture the coconut milk is used to braise meat and fish and let out curry pastes. The cream is a much more versatile product which can be used for desserts, curries and if you boil it down it splits to create coconut crack (a natural oil that comes from the reduction of moisture content in the coconut). Thanks for sharing – sebbyholmes

    • Jen Elizabeth's Journals
      August 3, 2013 / 9:48 am

      I had to check out The Begging Bowl online when I saw your comment – looks like some amazing food! 🙂

  7. August 3, 2013 / 2:13 pm

    Do you know the Stephanie Plum books? I love this serie in which main character is addicted to pastries and her favourite cake is pineapple upside down cake. I bet she would finish these in a second. I love the whipped coconut cream too, I usually serve it with a fruit salad, it gives it a nice exotic taste.

  8. August 3, 2013 / 6:39 pm

    These look AMAZING! And, you photos are so pretty! I love the coconut whipped cream, too. YUM!

  9. September 15, 2013 / 12:18 pm

    Jen, Those look absolutely delicious! I love the combo of pineapple and coconut. Pineapple with maple syrup and coconut cream – Yum! Great recipe – thanks

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