PINEAPPLE & ROSEMARY UPSIDE-DOWN CAKE

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I had always thought that upside-down pineapple cake sounded really good and should be this heavenly experience. Well, all the ones I have tried in the past few years, from one bakery or another, have been boring, dry and blah. That round slice of canned pineapple placed on top (in minis) and the rings (on the large) with those hard and dry red cherries… not my thing.

To be fair, I have to admit that I have not had the opportunity to try this cake from a good restaurant with a pastry chef, where the chance of a happy experience is much higher. I have also not found this type of “old-fashioned” cake available at any of the really good bakeries I usually recommend.

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Therefore, there was only one solution: come up with my own.
Add to that the fact that, whenever I ate some fresh pineapple, rosemary would pop in my mind as a good combination. I have thus known for some time that, whenever I would get around to baking this kind of cake, there would be rosemary in it.

And so I did. And the result is more divine than I ever imagined.

I started with my base apple cake recipe and modified it because I knew I would want to use brown sugar, rum, as well as some caramel-like sauce. This is the result: the absolutely best ever pineapple upside-down cake. Ever and ever!
Each and every person who has had a piece of this cake over the the past couple of years has moaned when eating it. Yes, that good, especially when still warm.
And it is easy, too.

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Here goes….

PINEAPPLE UPSIDE-DOWN CAKE WITH ROSEMARY

yields 1 round 9-inch cake, or 7-8 singles

• 1 fresh ripe but firm pineapple, peeled, cored and sliced (see notes)
• a couple of sprigs of fresh rosemary
• a few cherries in syrup: I like to use Amarene Fabbri or Toschi because they are fabulous, and you are also going to love them over vanilla ice cream

For the cake batter:

• 113 gr. (1 stick) unsalted butter, at room temperature
• 140 gr. (3/4 cup) dark brown sugar, well packed if measuring with cups
• 1 Tablespoon good quality dark rum (not spiced)
• 2 large eggs, at room temperature
• 1 teaspoon pure vanilla extract
• 165 gr. (1 cup) all purpose flour, sieved (you can use cake flour if you like)
• 1 teaspoon baking powder, sieved
• 1/4 teaspoon baking soda, sieved
• 1/4 teaspoon sea salt (or 1 teaspoon Kosher salt)
• 150 gr. (1/2 cup) whole plain yogurt

For the caramel sauce:

• 56 gr. (4 Tbsp or 1/2 stick) unsalted butter
• 140 gr. (3/4 cup) dark brown sugar, well packed if measuring with cups
• 2 Tablespoons good quality dark rum (not spiced)

You will also need:

A 9-inch in diameter (22 cm.) round cake pan with removable bottom, buttered and lined with parchment (see image below).

Or, if you prefer, 7 single ceramic ramekins, 8 fl. oz (240 ml) capacity, size: about 3.5-inch diameter and 2.5-inch height (about 10 cm. diameter, and 6.2 cm height) – see these on Amazon.

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1. Butter a 9-inch (22 cm.) cake pan with removable bottom and line it with parchment, leaving a skirt at the top (see image above).
2. Prepare the caramel sauce: place the 56 gr. (4 Tbsp) butter in a saucepan with the 140 gr. (3/4 cup) dark brown sugar and the 2 Tablespoons of rum. Bring to a simmer till the sugar and butter have melted and blended. Cook only for a minute or so and make sure you DO NOT let it caramelize.
   Pour it into the cake pan (see image below).

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3. Wash the rosemary sprigs gently under warm water (releases the flavor better), pat it dry, then sprinkle some leaves all over the caramel-rum sauce (see image below). Arrange a few of the cherries as well. The cherries are also dark, so they don’t pop color-wise, but the flavor will.

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4. Arrange the wedges of pineapple on top of the sauce, rosemary and cherries. Fit as much pineapple as you can. The advantage of slicing pineapple this way, besides making things easier, means that you get more pineapple per slice of cake.
Set aside.

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5. Preheat the oven to 350F / 176 C.

6. Place the sieved flour, baking powder, and baking soda in a bowl and blend. Set aside.

7. In a large bowl, place the 140 gr. (3/4 cup) dark brown sugar, the salt, and the 113 gr. / 1 stick butter in pieces and mix until well blended and fluffy. You can use a mixer with a paddle attachment at medium-low speed, or you can do like I do: wear a latex glove and use your hand, scraping all the bits well off your hand and back into the bowl when you are done.

8. Add the vanilla extract and the 1 Tablespoon rum and blend. At this point, if not using a mixer, I switch to a whisk.

9. Now add the eggs one at a time, making sure each egg is well incorporated before adding the next. Scrape down the bowl with a rubber spatula to make sure all the “scattered” bits are in the mix.

10. Add the yogurt and blend.

11. Then add the flour mix in 2-3 times, blending only until the white streaks of flour are no longer visible. Don’t overmix. Do: always scrape down the sides of the bowl with the rubber spatula as you work to make sure everything is well incorporated. This is valid for anything you bake: cakes, cookies, etc.

12. Pour the batter into the baking pan on top of the pineapple, and distribute evenly.

13. Bake for about 50-60 minutes or until a wooden skewer comes out clean.

14. Remove the cake from the oven and place on a rack to cool for about 30 minutes. Then, very carefully invert onto a cake platter, preferably with a lip to contain the juices. Unlock the ring and remove the cake pan. Then gently peel off the parchment, scraping down any sauce that wants to stick to it. You want all of it, as it is so good. Feel free to lick anything that remains on the parchment.

Serve the cake by itself or with some freshly whipped cream, or vanilla ice cream. You might also want to have some extra cherries on hand as everyone will want more.

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Notes:

About the pineapple: those perfect rings of canned pineapple…. are a NO NO! Honestly, I avoid anything canned as much as possible, especially fruit. The acidity in fruit interacts with the aluminum in the cans, and aluminum is toxic. Besides, I can taste anything canned a mile away. The only thing I allow from cans is tuna, and even that I prefer from glass jars. So, please, there is an abundance of lovely, fresh pineapple in just about every grocery store I go to: use one of those.
I did try the canned pineapple once on this cake, just to try, which is why I can tell you that there is no comparison. Use fresh.

The fresh pineapple for this cake is best ripe but firm. It can also be ok slightly under-ripe, as the sugar from the sauce makes up for the touch of sourness.

Slicing the pineapple: I have sliced it into rings and used those 2-3 times. It looks pretty enough, but it does not allow for a lot of pineapple per slice. So I started quartering the pineapple, then slicing it in thin wedges, which you can overlap and arrange decoratively. This way, everyone gets more pineapple per slice and it sill looks good. But this I leave up to you.

The caramel sauce: just simmer and stir (with a silicon spatula or a whisk) until the sugar and butter are melted and well blended. It won’t take long, so watch it. And seriously, don’t let it caramelize, because if you do (and I know from experience) the caramel will turn to liquid once the cake is baked and will run off the cake when you flip it. Once the cake is baked, the sauce is supposed to be gooey.

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Large cake vs. small singles: the one large cake is, of course, a bit quicker and easier to make. It also has the visual effect. The singles require a little more work and attention, as you have to butter and line each one with parchment, then distribute sauce, toppings and batter evenly.
But… the singles are my favorite, because you get more pineapple and gooey sauce per square inch of cake.

Know that if you opt for the singles, they will not need to bake as long. About 25-30 minutes will be enough. I have only done the singles once, and I would set the timer for 20 minutes, then check after that.

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One more thing: the cake has the potential to last at room temperature on a cake stand covered with a lid for 2-3 days on non crazy hot days. If it’s a hot summer and you want it to last, better store it covered in the refrigerator, and remove it at least 30 minutes before eating it.
Except this cake will not last at all. It will be gone in 24 hours max because it is so good. Therefore, it is really best to bake this cake on the same day you plan to serve it.

Let me know what you think if you make it!

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And if you would like more cake recipes, you can click on the image below.

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