Figure 1. Structures and IRI activity of small carbohydrate-based molecules.

(a) Structures of the first low molecular weight carbohydrate-based ice recrystallization inhibitors²⁵. (b) Structures of PMP containing phenolic-glycosides β-PMP-Gal (5), β-PMP-Glc, (6) and β-PMP-Man (7). (c) IRI activity of β-PMP-Gal (5), β-PMP-Glc (6), and β-PMP-Man (7) at 22 mM compared with sucrose (at 220 mM)²⁸, β-Octyl-Gal and –Glc (1–2 at 22 mM), and NOGal and NOGlc (3–4 at 0.5 mM)²⁵. All compounds are represented as a % MGS (mean grain size) of ice crystals (n = 108) relative to the PBS positive control. Error bars represent the standard error of the mean (SEM).