Pineapple Upside Down Cake for a Special Person

My organic delivery friend (yes, I have that luxury, and yes, I take full advantage of it! and if you live in KL, you can too!) sent over a beautiful ripe pineapple on Monday. Its been sitting on my counter, looking at me, and smelling of that unique sweet citrus pineapple-y smell that just seduces you into needing to eat it!

But I wanted to do something different, and also may be a little retro. Pineapple upside down cake is just stunning – beautiful pieces of caramelised pineapple and sticky gooey caramel adorning a perfectly simple, and yet deliciously tasty, vanilla cake. Buttermilk makes this tender, as does the melted butter. The cake itself is not very sweet, but that is because youre relying on the caramel to flavour the cake. Its easy to put together, as long as you are patient with the cutting of the pineapple – and have a VERY sharp knife. If you would rather have the old school pineapple rings, by all means cut them that way – you could even put a little cherry in the centre of each, or a strawberry or dried cranberry! But I like the chunky pieces of pineapple best – more rustic, a little less twee retro, craggier and more able to brown and suck up all that gorgeous caramel.

You will need:

• 1 sweet pineapple
• 1 stick of butter (8 tablespoons), divided into half (plus a bit for buttering tin)
• 1/2 cup of brown sugar
• 1 + 2 tbsp vanilla
• 1/2 cup white sugar
• 1 cup buttermilk
• 2 eggs
• 2 cups cake flour
• 1 teaspoon baking soda
• 1/2 teaspoon salt

Start by prepping. You will need to preheat your oven to 175C, and butter a 9 inch round cake tin very well. Once the cake tin is buttered, prepare a sling made of parchment or baking paper. Tear a sheet that is twice as long as the width of your tin, and centre over the buttered tin. Push it in, and using the butter as a kind of glue, ensure that the paper adheres to the bottom and sides of the tin. Rebutter the sheet of baking paper, up to the sides as well. Set aside.

Prepare your pineapple. You will need a very sharp knife, otherwise please dont attempt this as you may chop a finger off! Resting the pineapple on its now stable bottom, use your knife to peel off the skin. Cut in half lengthwise, and then into quarters. Once the skin is off, you will need to get the brown “eyes” that stay within the indentations. Use your knife again, working slowly and carefully, at an angle, against the pineapple. You will see that its possible to make triangluar cuts into the pineapple in long strips to take off these pesky bits. Once the pineapple is clean, cut out the woody interior, and chop roughly. Set aside once you have prepared the entire pineapple.

Melt 4 tablespoons of butter in a large pan over high heat. Once the butter has been melted, add all the pineapple, and ensure that it is in one layer at the bottom of the pan. Allow it to brown and caramelise in the butter, flipping over only a few times, for about 5 to ten minutes or so. Sprinkle over about half the brown sugar, and mix, and allow to cook, all in one layer, for a few minutes. Add the rest of the brown sugar, mix, and let bubble for a bit. Add about 1 tablespoon of vanilla (be careful, it will hiss and spit at you!), and mix well.

Using your spatula, transfer all the pineapple and gorgeous caramel into your baking tin. Ensure that it coats the entire bottom of the tin, and the pineapple is well layered. Set aside.

Add the remaining 4 tablespoons butter to the hot pan – it should melt quickly. Once melted, transfer immediately to a heatproof bowl, and whisk in white sugar, buttermilk, eggs and remaining vanilla. Once the mixture is foamy, set aside while you mix dry ingredients together (I usually just measure out the flour, add the baking soda and salt to the measuring cup and mix with spoon).

Using a spatula, mix the dry ingredients into the wet mixture. Taste for vanilla, and add more if its to your liking. Spoon or pour the batter over the caramelised pineapples in the tin and smooth the top over. Bake in your hot oven for 50 – 60 minutes (checking at about 45) or until a toothpick inserted into the centre of the cake comes out clean.

Take the tin out of the oven, and let it rest for at least ten to fifteen minutes, over a cookie rack. This waiting time is really important, to let the caramel set up, so that when you flip it over, the while thing wont run in rivers over your countertop! Be patient! Once the tin is lukewarm and handleable, invert the tin over a cake plate, using the paper sling to coax it out. Peel the parchment off gently, and adjust any pineapple bits that may have fallen off. Let the cake rest for at least another 10 minutes or so before slicing.

You could serve this with some creme fraiche, a few strawberries, or some vanilla ice cream, but thats kind of gilding the lily! Its beautiful as is, and such a wonderful tribute to the prickly pineapple.

Cooks Note: you can bake this without the parchment sling. It will definitely make the caramel stickier and richer in colour and flavour. I decided against it because I wanted a lighter version of the cake but feel free to eschew the parchment sling. In that case, rest for only up to ten minutes when it comes out the oven.

Tags: cake, caramel, dessert, pineapple, recipe, sweet, vegetarian