Preheat oven to 350°F. Line a 12-cup cupcake pan with paper baking cups.
In a large bowl, mix butter and sugar with an electric mixer or hand-held mixer until light and fluffy, about 5 minutes.
Stir in the egg whites, one at a time, blending well after each one. Stir in the vanilla and flour just until mixed. Add milk as needed. You want the batter to be similar to a pancake batter consistency. Spoon the batter into the prepared cups, dividing evenly.
Bake until the tops spring back when lightly pressed, 18 to 20 minutes. Cool in the pan set over a wire rack.
FILLING
Place jam into a piping bag fitted with a 230 tip. Press tip into the baked and cooled cupcake at least half-way down and apply pressure to the piping bag.
Slowly start to move tip up and out of the cupcake applying pressure the whole time. Repeat on all cupcakes.
CREAM CHEESE FROSTING
In the bowl of a stand mixer, combine butter, cream cheese, confectioners' sugar, and vanilla. Mix until creamy, about 3-5 minutes.
Place frosting into a piping bag fitted with a 1M tip. Pipe out cream cheese swirls over the cupcakes that have been filled with jam.
Chill until ready to serve.
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