0.9 oz × 29.57 ml × 0.789 g/ml = 21 g · about 147 kcal from the alcohol alone
IN THE GLASS
VANILLIN
FROM RYE · from oak barrel aging
Formula
C₈H₈O₃
Mass
152.15 g/mol
IUPAC
4-hydroxy-3-methoxybenzaldehyde
Bourbon's fingerprint, extracted from the charred American oak the law requires for aging. Same molecule as the vanilla bean's signature, so a well-aged bourbon legitimately tastes like vanilla. Chemistry, not metaphor. Cognac, aged rum, tequila reposado all extract vanillin from oak too. Different barrels, same molecule.
Lemon's defining note: technically a mix of two geometric isomers (geranial and neral) that read as the same aroma to the nose. Lemon peel, lemongrass, lemon verbena, and Indian chai all carry it. In cocktails it's what a lemon twist contributes that lemon juice can't: the volatile expressed from the oil glands, not the acid from the pulp.
An orange rind, squeezed, throws a spray that catches the light. That's d-limonene boiling off. It's roughly 95% of orange peel oil by mass, and the molecule that puts the "orange" in orange anything. Used industrially as a green solvent because the chemistry that dissolves citrus oils also dissolves greasy machinery. The expressed-peel garnish on a cocktail is delivering vaporized limonene to the rim of the glass.
Rye, lemon, orange and grenadine. Pomegranate-derived grenadine gives the fruit-forward backbone, while citral from lemon and d-limonene from orange build the nose. Named for the Boston electoral district where it was supposedly conceived.
PROVENANCE
Said to have been created at Locke-Ober's bar to celebrate the predicted victory of Martin Lomasney for state representative of Boston's Ward 8. The drink was prepared the night before the election; the candidate won. Early recipes call for whiskey, not gin; the earliest printed description is a 1915 trademark notice, and Locke-Ober reopened its bar after Prohibition with a rye recipe.