0.81 oz × 29.57 ml × 0.789 g/ml = 19 g · about 132 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.
The grape-candy / Welch's-grape-juice aroma. Concord grapes carry it in concentrations no European wine grape (Vitis vinifera) approaches; American Vitis labrusca grapes, native to the northeastern US, hold methyl anthranilate as a signature. The "foxy" note in North American grape juice and artificial grape candy both come from the same molecule. Also used as the standard bird repellent on commercial fruit crops; birds find it intolerable.
The bitter from gentian root, used across Campari, Aperol, sweet vermouth, Angostura, and most amari. Bitter compounds activate TAS2R taste receptors that evolved to detect plant alkaloids. The same machinery that makes broccoli taste bad to children also makes a Negroni taste like an adult ordered it.
Rye, dry vermouth and pineapple juice. The unexpected element is the pineapple: ethyl esters from fresh juice brighten what would otherwise be a dry Manhattan. It is reputedly named for the Algonquin Hotel.
PROVENANCE
The Algonquin Hotel was famous through the 1920s for the 'Algonquin Round Table', a daily lunch of literary figures (Dorothy Parker, Robert Benchley, Alexander Woollcott, Robert Sherwood). The cocktail said to be named for it postdates the Round Table's heyday, first appearing in print in 1935, in G. Selmer Fougner's Along the Wine Trail. Pineapple in a whiskey cocktail was contemporary novelty; modern bartenders sometimes view the drink with skepticism, but the recipe is well-formed and the pineapple actually works.