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In the bowl of an electric mixer, fitted with the dough hook attachment, combine flour, sugar, yeast, eggs, milk and salt. Stir to combine on low speed. Once combined, begin adding butter, a couple of cubes at a time, until the dough comes together (it will be a little sticky). Remove the dough from the bowl onto a lightly floured surface and knead for 3-4 minutes or until the dough is shiny and tacky. Cover and set aside while you make the filling.
Heat a double boiler over medium heat (fill a medium saucepan a 1/4 of the way full with water and bring to a simmer. Once simmering, place a metal bowl on top of the pan). Add chocolate chips and butter, stir consistently until the chocolate and butter have melted. Remove from the heat and stir in the powdered sugar, cocoa and balsamic, creating a paste. Roll the dough into a long rectangle that’s roughly 1/2-inch thick. Spread filling over the dough, leaving a 1-inch border around the edge. Roll the dough into a tight, long, cylinder. Cut the roll in half, long-ways, creating two halves. Braid the halves together into a loose plait. Place the plait into a parchment-lined loaf pan, tucking the ends under the ‘loaf’ to fit. Cover with a towel or plastic wrap and set aside (in a warm place) for 2 hours to proof and rise.
Preheat oven to 375°F. Once the dough has risen, remove the wrap and brush with egg wash. Place in the oven and bake for 15 minutes. After the first 15 minutes, reduce oven temperature to 335°F and continue to bake for 25-30 minutes or until golden brown and cooked through (insert a toothpick into the center, if it comes out clean, the babka is baked). Set aside to cool to room temperature.
Combine granulated sugar and water in a small saucepan. Stir to combine and bring to a simmer, simmer for 3-4 minutes or until the sugar has dissolved and the mixture is syrupy. Remove from the heat and set aside to cool (and further thicken into a glossy glaze). Pour glaze over the babka and set aside to harden slightly.
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