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Table 2 1H- and 13C-NMR data (700 MHz, CD3OD) for biosynthesized (−)-menthol β-glucoside and (−)-menthol β-galactoside

From: Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation

Position (−)-Menthol β-glucoside (−)-Menthol β-galactoside
δH (multi., J in Hz) δc δH (multi., J in Hz) δc
1 3.57 (1H, ddd, 10.6, 105, 4.2) 78.4 3.57 (1H, ddd, 10.8, 10.8, 4.4) 78.4
2 1.24 (1H, m) 49.5 1.22 (1H, m) 49.5
3 1.03 (1H, m); 1.63 (1H, m) 24.3 1.03 (1H, m); 1.65 (1H, m) 24.4
4 0.84 (1H, m); 1.68 (1H, m) 35.8 0.85 (1H, m); 1.67 (1H, m) 35.8
5 1.37 (1H, m) 32.9 1.38 (1H, m) 32.9
6 0.94 (1H, m); 2.12 (1H, m) 41.8 0.93 (1H, m); 2.13 (1H, m) 41.8
7 2.31 (1H, m) 26.3 2.31 (1H, m) 26.3
8 0.81 (3H, d, 6.8) 16.4 0.79 (3H, d, 7.2) 16.4
9 0.87 (3H, d, 7.1) 21.6 0.89 (3H, d, 7.0) 21.6
10 0.93 (3H, d, 6.6) 22.8 0.96 (3H, d, 6.8) 22.8
1′ 4.35 (1H, d, 7.8) 101.4 4.35 (1H, d, 7.6) 101.5
2′ 3.14 (1H, m) 75.2 3.14 (1H, m) 75.2
3′ 3.35 (1H, m) 78.3 3.35 (1H, m) 78.3
4′ 3.31 (1H, m) 72.0 3.30 (1H, m) 72.1
5′ 3.24 (1H, m) 77.8 3.24 (1H, m) 77.8
6′ 3.67 (1H, dd, 11.6, 5.4);
3.84 (1H, dd, 11.6, 2.3)
63.1 3.67 (1H, dd, 11.6, 5.2);
3.84 (1H, dd, 11.6, 2.4)
63.2