Caramelized Pineapple Upside-Down Cake

This is not the pineapple upside-down cake that I used to make back in the day, you know the one with the canned pineapple and maraschino cherries from the Betty Crocker cookbook.  This cake is all grown up with a  vanilla bean scraped into the cake batter and a splash of brandy.  My pineapple upside-down cake is an elegant cake fit for a special dinner party or just for some seriously scrumptious dessert eating, preferably shared with family or friends.  I spent some time doing a little research for an updated version of the recipe and ended up using a combination of ingredients that sounded good to me in all the recipes I found.  The idea of using brandy and a vanilla bean in the batter came from “In The Sweet Kitchen” by Regan Daley.  If you like to bake you should seriously consider adding this cookbook to your collection.  I find myself using this cookbook as a reference for many things I bake as it is full of fabulous recipes for just about any kind of dessert as well as tips on techniques and tons of information on ingredients.  I also went to a cookbook new to my collection, ‘Flour’ by Joanne Chang for her recipe for old fashioned pineapple upside-down cake as well as ‘The Cake Bible’, another one of my favorites by Rose Levy Beranbaum.  I decided to leave out the sweet cherries as well as pecan halves and just go with the slices of pineapple in the topping.  Why?  Because that’s my favorite part of the cake and I didn’t want any of those cherry or pecan halves getting in the way of my caramelized pineapple slices.  I sliced a fresh pineapple into thick slices then simmered them in caramel sauce on top of the stove, that would be good all by itself served on top of vanilla ice cream.  An upside-cake can also be made in a cast iron skillet which saves the step of transferring the caramelized fruit into a cake pan before pouring in the cake batter and placing in the oven.  I like to use a cake pan for this recipe just because it’s how I’ve always done it so I guess I do honor some traditions, for sure the good ones.

Ingredients and Directions for Caramelized Pineapple Upside-Down Cake
1 pineapple
1 3/4 cups sugar, separated 1 cup and 3/4 cup

1/2 cup water
6 tablespoons unsalted butter, cut into pieces, plus 1/2 cup melted and cooled
1 cup all purpose flour
1 teaspoon baking powder
1/4 teaspoon sea salt
2 eggs, at room temperature
3 egg yolks, at room temperature
1/2 vanilla bean, seeds scraped out
2-3 tablespoons brandy, or a very generous splash

Preheat the oven to 350 degrees 
Generously butter a 9 inch cake pan

Slice off the top and bottom of your pineapple so it sits evenly on your cutting board.  Using a heavy knife peel, halve and core the pineapple.  Cut each half of the pineapple in half and then cut into slices 1/2 inch thick.

Put 3/4 cup sugar in the bottom of a heavy medium saucepan.  Add the water, swirl pan to moisten the sugar.
Place the pan over a high heat and bring to a rolling boil.  Don’t stir just let it boil until the sugar bubbles all over and starts to turn brown.  This will take 4-5 minutes.  The sugar will turn brown, thicken and turn syrupy.
Carefully swirl the pan to evenly caramelize the sugar.  Lower the heat and carefully whisk in the pieces of butter.  Add the slices of pineapple to the bubbling caramel very carefully!  Simmer the pineapple for about 10 minutes.  Transfer the pineapple slices to the prepared cake pan  arranging in a circular pattern, covering as much of the bottom as possible.

In a medium bowl sift together the flour, baking powder and salt.  In a large bowl whisk together the eggs and egg yolks until very well blended.    Slowly whisk in the sugar, vanilla seeds, generous splash of brandy and melted butter.  Using a large rubber spatula fold the flour mixture into the egg/sugar mixture until combined.

Pour the batter over the pineapple slices in the cake pan, making sure the batter fills in evenly around the slices.  Bake for 45-50 minutes until the top is golden brown and the top of the cake springs back when lightly pressed with a fingertip.

Cool the cake on a wire rack for at least 30 minutes before turning out upside down on a serving plate.  Run a knife along the inside edge of the pan to help separate the cake from the pan.  Place your serving plate on top of the cake and carefully flip upside down.  Lift off the cake pan and continue to let the cake cool before serving.  If a piece of pineapple sticks to the bottom of the pan just replace it back on top of the cake.  The cake is best served the same day you make it, but can be stored for a few days in an airtight container at room temperature.

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  1. What a glorious creation. The caramel on your cake couldn't be more perfectly colored. This sounds delicious. I hope you have a great day. Blessings…Mary

  2. Tempted. I took on your pear upside down cake before and this sounds really tempting to get my hands on! The cake looks fluffy and the top is caramelized perfectly. YUM!

  3. I make something simila and I just love your version. I just became a follower. I also have a blog, but unfortunately it diappeared after 13 months and now working on switching to WordPress. Will let you know when its up arounf mid May. I really like your work.

  4. It's gorgeous & all grown up! Love it.

  5. Oh, that looks delicious! My mom used to make this cake all the time when I was growing up and those pineapple slices were like finding a treasure when the cake was flipped over:)

  6. Oh! Your pineapple upside-down cake looks delicious…would love to have it with a cup of tea. Have a great week ahead Patty :-)

  7. that is one beautiful cake! Oh we love pineapple upside down cakes, the buttery richness of the cake and all that ooey gooey caramel with those super sweet pineapples…..sigh….you got it all going on here. How I wish I could have a slice for dinner tonite!
    I love Regan's book too! I have to start re reading my cookbooks for some inspiration!

  8. Your cake looks picture perfect! So wonderful with the vanilla bean and the addition of brandy!

  9. I grew up on the old version but I'm learning towards yours, just don't tell my mom. I love the little crunch the vanilla bean adds. I don't have Regan's book, will have to look for that.

  10. The sugary brown topping looks fantastic! And the pineapple looks so juicy!

  11. I love your version of caramelized upside down cake. So pretty and delicious!

    Thank you for the bid, on my chocolate chip biscotti, Patty…stop by my blog, and check it out. Just made it today…ready to be shipped:DDD

  12. Hahaha! I had to laugh at —> ” I didn't want any of those cherry or pecan halves getting in the way of my caramelized pineapple slices”. My kinda foodie. Knows what she likes and goes right after it. You make me so proud :-D. On a more serious note though, this cake looks moist, beautiful, and scrumptious. Loving your plate also by the way. Thank you for another great recipe, Patty.

  13. Given that I am currently a few months into my free-pineapples-for-a-year bonanza, I'm on the lookout for pineapple recipes and I am quite taken by your grownup cake. I'm a grown-up, after all, even if I don't often act like it. I promise I am.

  14. Stunning pictures, Patty! I love the grown-up flavors and elegance of this cake!

  15. This grown up pineapple upside down cake looks and sounds fabulous! I think I like this version better than the one with cherries. I am very tempted to try this as the Costa Rican pineapples sold at the stores now are just delightful. BTW, your dish with the blue trimming is just gorgeous!

  16. I love your version of pineapple upside down cake. :) This was my mother in law's signature dessert, and I haven't had it in years. Yours is giving me a craving for it!

  17. What a lovely upside down cake! Pictures are great too.

  18. You know, I have only ever associated this cake with the canned type of pineapple, and yet here you really have made a very elegant reinterpretation of this. The caramelized pineapple, vanilla bean, and brandy really elevate this!

  19. Now this is exactly what I think of and dream of when I hear pineapple upside or rightside up cake :) Patty your photos are gorgeous and your recipe is delectable. Everything is just perfect!

  20. This cake is gorgeous! This is my first visit to you blog, which is fantastic! Looking forward to following your posts! Your photos are really stunning. Cheers!

  21. Patty, it's been way too long since I've baked or eaten up-side-down cake! Maybe I'll make myself one for Mothers Day!

  22. Patty, this looks incredible. I have that cookbook but haven't made anything from it. This looks like a keeper.
    Also, I've tagged you over at my blog for a game of food tag, if you care to play!

  23. I love how you tell us about your research, and your musings and decisions! It is as if we could see you reading, thinking, trying…for a marvellous result!

  24. Love the grown-up version of a classic. We love upside down cakes with their gooey yumminess on top.

  25. Absolutely gorgeous…both the cake and photos! Love the bit of brandy, delicious :)

  26. Anonymous says:

    I will be making this cake for my family's Easter Sunday Dinner. I am so excited to make this Pineapple Upside Down Cake; All Grown Up!

  27. Chrissie says:

    VERY good. I don’t usually care for pineapple upside-down cake, nor do I usually make changes to a recipe before trying it as originally written. But I didn’t have brandy, so I used rum, and I don’t own a 9″ cake pan (hard to find one here in the town where I live in Mexico), so I used an 8″ square pan and baked it for the full 50 minutes. PERFECT! It was delicious and a nice change from the cloyingly sweet brown sugar versions!

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