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This retro favorite was popularized by the Hawaiian Pineapple Company and Gold Medal Flour in the 1920s. Here, the classic goes autumnal with the addition of pumpkin, molasses, and a mix of warming spices.
Ingredients
Makes 10 servings
Topping:
Cake:
For topping:
Step 1
Preheat oven to 350°F. Spray 9x9x2-inch metal baking pan with nonstick spray. Combine sugar, butter, pineapple juice concentrate, and molasses in heavy small saucepan. Bring to boil over medium heat, whisking until sugar dissolves and syrup is smooth; boil 1 minute. Pour evenly into prepared pan.
Step 2
Cut off one 1/3-inch-thick round from pineapple; cut out core. Place round in syrup in pan. Stand pineapple on end. Cut lengthwise into 1/3-inch-thick slices. Using 3 round cutters of different sizes, cut out rounds from pineapple slices, avoiding core. Arrange rounds close together in single layer in free-form design in syrup.
For cake:
Step 3
Whisk first 6 ingredients in medium bowl. Beat butter in large bowl until fluffy. Add sugar and beat to blend. Beat in eggs, 1 at a time. Beat in molasses, then pumpkin. Beat in dry ingredients just until blended, occasionally scraping down sides of bowl. Beat in 1/2 cup boiling water. Pour batter evenly into pan.
Step 4
Bake cake until tester inserted into center comes out clean, about 50 minutes. Cool cake in pan 45 minutes. Place platter over pan and invert. Let stand 5 minutes. Gently lift off pan. Serve cake warm or at room temperature with whipped cream.
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Reviews (26)
Back to TopI made this recipe with gluten free flours. The cake portion was very good, but the pineapple made the top too soggy. I personally did not care for the combined taste of the cake and the pineapple. Think the cake by itself would be delicious just dusted with powdered sugar and a dollup of whipped cream. I would make this again, but without the pineapple.
rose_hoppe
Los Osos, CA
1/30/2017
Fantastic recipe. Really simple to make. I made a half quantity although I kept the spicing to the full recipe quantities and would still have liked a little more. It took even longer to cook than the recipe suggested, but it really was good. The cake itself is beautifully moist and light and the pineapple topping delicious. I will definitely be making this again.
Anonymous
california
10/14/2014
Loved this recipe as did all of my guests. I made 11/2 recipe, using 1/2 molasses and additional pumpkin as others have suggested. Also used canned pineapple.
vallariok
NJ
10/12/2013
A real "four-forker," however, I did make changes. First, I made a 9x11 cake (1 1/2 recipe). Next, several people commented that this cake was too sweet. The cake sounded really wonderful, but we prefer less sweetness in our desserts. I used regular, Dole unsweetened pineapple juice for the topping and less brown sugar. I was a little short on the molasses, so I made up for it with agave syrup. I also reduced the sugar and molasses in the cake. I did need to reduce the topping down further since it was very thin. I wasn't sure it was going to work since the topping was very liquid. After taking the cake from the oven, I doubted it very much. I let the cake sit over night, then inverted in in the morning. It was REALLY good. We brought it on a camping trip, so it was wrapped in foil, but not refrigerated at all for 4 days. On the fourth day, the cake was still moist and very tasty. We still have a bit left, so I'm going to see if it freezes.
CookingInMorroBay
Morro Bay, CA
7/8/2013
Way too sweet. Stick to the regular pineapple upside down cake.
btydew
Boston, Ma
5/7/2013
does Arizona cook understand that this is an upside-down cake: e.g. you put the fruit on the bottom of the pan, then invert after cooking????!
Anonymous
Northern Calif
1/7/2012
我需要弄清楚如何处理一些leftover pumpkin and a pineapple my husband randomly brought home. I wasn't sure the pineapple, pumpkin and gingerbread would all go together, but they really did. My only criticism of this cake is that it is what I would describe as tooth-achingly sweet. However, I do not have much of a sweet tooth and my husband really enjoyed it. I would probably make this again if I had the ingredients on hand, but I'm not sure I would go out of my way to make it. Still, overall, it was very good.
mellibot
Delaware
11/23/2011
Easy, tasty and great presentation what else do you need? I did one and a half times the recipe and put it in a 9x13 pan. Used canned pineapple rings and the juice from same instead of the frozen concentrate. Served it with ginger whipped cream. Amazing. Making it again this weekend.
Anonymous
Orchard Park, NY
11/17/2011
Delicious! I will definitely be making this again, and again, and again...
ldub6350
Seattle, WA
10/27/2011
i made a few substitutes to this recipe to make it vegan (i.e. to contain no animal products) and it turned out delicious. I simply used dairy-free margarine (Earth Balance) in place of the butter called-for, and used 4 tsp. of whizzed chia seed blended with 1/2 cup of water in place of the eggs. I also happened not to have canned pumpkin in the house, so I used the equivalent volume of mashed ripe banana. The results were light, moist, and delicious. looked pretty too.
stipendous
4/18/2011
This was absolutely delicious! I had leftover pineapple I wanted to use up that had been in the freezer--chunks and crushed (which I drained). I don't think I'd go through the trouble of using fresh, since this came out so well.
Anonymous
Boston, MA
1/18/2011
Fabulous! My step-daughter made it while we were visiting for Thanksgiving. She used OJ instead of frozen pineapple juice, and FRESH PINEAPPLE, which was key. Kids, husband, us, and the whole family loved it. Moist and delicious. I plan to make it this weekend to thank the people who took care of our pets while we were visiting.
mindgardener
philadelphia
12/2/2010
I made this exactly as the recipe said, but I couldn't get it to float above the plate like it does in the picture. what gives?
Anonymous
arizona
9/26/2010
WOW, this cake is fantastic! I followed the recipe exactly but used canned pineapple rings, drained and patted dry. I think the pumpkin added texture rather than flavor and the moistness of this cake is incredible. One tip: if using a 9x9 pan, put something to catch the dripping sugar topping under one of your oven racks as it really made a mess of my oven. Also, let it cool AT LEAST 45 minutes, this will make it come out of the pan perfectly intact. This is going to be on my dessert table come Thanksgiving!
itsmecissy
Watsonville, CA
9/20/2010
I made it with canned pineapple for company and the entire family loved it, especially with a shot of whipped cream on the side. I had no problem with it being underdone. This one is a keeper.
wallymama
1/16/2010