2.31 oz mixed with ice, 0.83 oz of it pure alcohol
Melt
Stirred: +15 % of the pre-batch, +0.35 oz of water
Served
2.31 + 0.35 = 2.66 oz in the glass
Strength
0.83 ÷ 2.66 = 31.1 % ABV as served
Ethanol
0.83 oz × 29.57 ml × 0.789 g/ml = 19 g · about 135 kcal from the alcohol alone
IN THE GLASS
VANILLIN
FROM BOURBON · 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.
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.
Bourbon, sugar, Angostura and an expressed orange peel. There is no mixer and dilution is minimal, so the spirit is barely cut and the ABV stays near 32%. Vanillin from charred oak carries the signature, and d-limonene from the peel opens the nose. Congener load is high, as in most barrel-aged spirits.
PROVENANCE
The name refers to the construction method that predated the 1870s–80s wave of fancier cocktails dressed with liqueurs: spirit, sugar, bitters, water, stirred over ice. Bartenders making newer drinks called the bare-essentials version an old-fashioned cocktail; the modifier became the name. The term was in print in Chicago by 1880; Louisville's Pendennis Club, founded in 1881, later claimed the invention, though the construction is older.