*2.1. Chemicals and Reagents*

Commercial standards include (+)-catechin hydrate ( ≥98%), ( −)-epicatechin ( ≥90%), rutin hydrate ( ≥95%) and quercetin ( ≥95%) were purchased from Sigma-Aldrich (Auckland, New Zealand). Acetonitrile (MeCN, HPLC grade), L-(+)-tartaric acid (reagent grade), acetone (analytical grade) and ethanol (analytical grade) were purchased from ECP (Auckland, New Zealand). Glacial acetic acid (AcOH, HPLC grade) was purchased from ThermoFisher Scientific (Auckland, New Zealand). Ultrapure water (H2O) had resistivity of 18.2 M Ω cm and was obtained from Sartorius Arium® Pro system. Pinot noir grape pomace (seeds, skins and stems) was industrially sourced from a New Zealand vineyard in 2015. Acylating agents (octanoyl chloride, lauroyl chloride and palmitoyl chloride) were purchased from Sigma-Aldrich (Auckland, New Zealand).

### *2.2. Preparation of Model Red Wine and Solvent Systems*

Model red wine was prepared by dissolving tartaric acid (5 g) into 13.5% EtOH in ultrapure water (1 L). The pH of this solution was adjusted to 3.5 with NaOH (10 M and 1 M).

A subset of 28 systems were selected (from those used in the literature) and trialed in extraction on small-scale mass Pinot noir pomace samples (see Section 3.1) [30]. The ratios of the solvents (acetone, H2O and EtOH) that made up the selected systems (50 mL) are found in Table 1.

**Table 1.** Solvent systems trialed for solvent–liquid extraction of Pinot noir pomace.

