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1
Place an oven rack in the lower third of the oven and preheat the oven to 350F.
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2
Butter and flour a 9 x 5 x 3-inch nonstick loaf pan.
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3
In a medium bowl, combine the flour, baking powder, orange zest, cinnamon, and salt.
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4
Whisk to combine.
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5
Place 3 tablespoons of the flour mixture in a small bowl.
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6
Add the mashed raspberries and gently toss until coated (the mixture may clump).
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7
In a stand mixer fitted with the paddle attachment, beat together the granulated sugar and butter until light and fluffy, about 2 minutes.
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8
With the machine running, add the eggs one at a time.
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9
Add the vanilla extract.
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10
Add the dry ingredients, a small amount at a time, mixing until just incorporated.
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11
Gently fold in the raspberries with a rubber spatula (see Cooks Note).
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12
Pour the mixture into the prepared pan and bake until a cake tester inserted into the center of the cake comes out clean, about 1 hour.
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13
Cool for 20 minutes.
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14
Remove the cake from the pan and transfer to a wire rack to cool completely.
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15
To make the vin santo cream: In the bowl of an electric mixer fitted with the whisk attachment, whip the heavy cream until it holds soft peaks.
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16
Add the vanilla extract, confectioners sugar, and vin santo.
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17
Continue to whip until the cream holds stiff peaks.
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18
Transfer the pound cake to a serving platter.
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19
Slice and serve with a dollop of the vin santo cream.
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20
Make sure you barely fold in the mashed raspberries so you get a pretty marbled effect; if you mix too vigorously, the raspberries will break down and turn the pound cake purple.