Ingredients:
2 c. sugar, divided
3 Tbsp. plus 2 c. all-purpose flour, divided
1/2 c. milk
1/2 c. plus 1/3 c. shortening, divided
2 eggs
1 bottle (1 oz.) red food coloring
1 Tbsp. white vinegar
2 tsp. vanilla extract, divided
3 Tbsp. baking cocoa
1 tsp. baking soda
1 c. buttermilk
1/2 c. butter, softened
3 Tbsp. confectioners' sugar
FROSTING:
1 c. (6 oz.) semisweet chocolate chips
1/3 c. plus 1-3 tsp. evaporated milk, divided
1 1/2 c. confectioners' sugar
Directions:
In a heavy saucepan, combine 1/2 c. sugar, 3 Tbsp. flour and milk until smooth. Bring to a boil; cook and stir 1-2 minutes or until thickened. Remove from the heat; cool.
In a large bowl, cream 1/2 c. shortening and remaining sugar until light and fluffy. Add eggs, one at a time, beating well after each addition. Beat in the food coloring, vinegar and 1 tsp. vanilla. Combine the cocoa, baking soda and remaining flour; gradually add to creamed mixture alternately with buttermilk, beating well after each addition.
Fill paper-lined muffin cups 2/3 full. Bake at 350 degrees for 20-25 minutes or until a toothpick inserted near the center comes out clean. Cool for 10 minutes before removing from pans to wire racks to cool completely.
In a small bowl, beat butter and remaining shortening until smooth. Beat in the confectioners' sugar, cooled sugar mixture and remaining vanilla until light and fluffy, about 3 minutes. Insert a large round tip into a pastry or plastic bag; fill with filling. Inset the tip halfway into the center of each cupcake and fill with a small amount of filling.
For frosting, in a heavy saucepan, melt chips with 1/3 c. evaporated milk over low heat; stir until smooth. Remove from the heat. Beat in confectioners' sugar. Add enough remaining milk to achieve spreading consistency. Frost cupcakes.
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