1H NMR spectroscopic data for the synthesized compounds in acetone-d6.
| Atom | Rutin (2) | Rutin butyrate (3a) | Rutin octanoate (3b) | Rutin laurate (3c) | Rutin palmitate (3d) | Rutin stearate (3e) | Rutin oleate (3f) |
|---|---|---|---|---|---|---|---|
| δ H (ppm), J (Hz) | δ H (ppm), J (Hz) | δ H (ppm), J (Hz) | δ H (ppm), J (Hz) | δ H (ppm), J (Hz) | δ H (ppm), J (Hz) | δ H (ppm), J (Hz) | |
| 5 | 12.40 bs | 12.47 bs | 12.44 bs | 12.45 bs | 12.47 bs | 12.47 bs | 12.47 bs |
| 6 | 6.28 d (2.1) | 6.28 d (2.0) | 6.27 d (2.1) | 6.27 d (2.1) | 6.27 d (2.1) | 6.28 d (2.0) | 6.28 d (1.9) |
| 8 | 6.52 d (2.1) | 6.50 d (2.0) | 6.51 d (2.1) | 6.50 d (2.1) | 6.50 d (2.1) | 6.50 d (2.0) | 6.50 d (1.9) |
| 2′ | 7.81 d (2.2) | 7.80 d (2.1) | 7.79 d (2.2) | 7.78 d (2.1) | 7.78 d (2.1) | 7.80 d (2.1) | 7.80 d (2.1) |
| 5′ | 6.97 d (8.5) | 6.97 d (8.5) | 6.97 d (8.5) | 6.97 d (8.5) | 6.97 d (8.5) | 6.98 d (8.5) | 6.98 d (8.4) |
| 6′ | 7.73 dd (8.5, 2.2) | 7.71 dd (8.5, 2.1) | 7.69 dd (8.5, 2.2) | 7.70 dd (8.5, 2.1) | 7.70 dd (8.5, 2.1) | 7.69 dd (8.5, 2.1) | 7.70 dd (8.4, 2.1) |
| 1′′ | 5.17 d (7.6) | 5.36 d (7.2) | 5.33 d (7.2) | 5.34 d (7.3) | 5.34 d (7.3) | 5.35 d (7.2) | 5.35 d (7.0) |
| 2′′ | 3.45 m | 3.48 m | 3.48 m | 3.47 m | 3.47 m | 3.47 m | 3.45 m |
| 3′′ | 3.48 m | 3.48 m | 3.48 m | 3.47 m | 3.47 m | 3.49 m | 3.48 m |
| 4′′ | 3.39 m | 3.39 m | 3.38 t (9.0) | 3.38 m | 3.38 m | 3.38 m | 3.38 t (8.7) |
| 5′′ | 3.39 m | 3.43 m | 3.42 dd (5.7, 1.3) | 3.42 dd (5.7, 1.1) | 3.42 dd (5.6, 1.2) | 3.43 dd (5.8, 1.2) | 3.43 dd (5.7, 1.1) |
| 6′′α | 3.78 d (11.4) | 3.87 dd (10.9, 1.0) | 3.85 dd (10.8, 1.3) | 3.85 dd (10.7, 1.1) | 3.85 dd (10.9, 1.2) | 3.87 dd (11.0, 1.2) | 3.87 dd (10.9, 1.1) |
| 6′′β | 3.45 m | 3.52 m | 3.51 dd (10.8, 5.7) | 3.51 dd (10.7, 5.7) | 3.51 dd (10.9, 5.6) | 3.51 dd (11.0, 5.8) | 3.52 dd (10.9, 5.7) |
| 1′′′ | 4.56 s | 4.62 s | 4.61 s | 4.61 s | 4.61 s | 4.61 s | 4.61 s |
| 2′′′ | 3.65 dd (3.3, 1.4) | 3.70 bs | 3.69 bs | 3.70 bs | 3.70 bs | 3.69 bs | 3.70 bs |
| 3′′′ | 3.58 dd (9.3, 3.3) | 3.69 m | 3.68 dd (9.5, 3.4) | 3.68 dd (9.5, 3.3) | 3.68 dd (9.5, 3.2) | 3.68 dd (9.4, 3.6) | 3.67 dd (9.5, 3.3) |
| 4′′′ | 3.33 t (9.3) | 4.81 t (9.2) | 4.81 t (9.5) | 4.81 t (9.5) | 4.81 t (9.5) | 4.81 t (9.4) | 4.81 t (9.5) |
| 5′′′ | 3.48 m | 3.62 m | 3.61 dq (9.5, 6.3) | 3.60 dq (9.5, 6.3) | 3.60 dq (9.5, 6.3) | 3.60 dq (9.4, 6.2) | 3.61 dq (9.5, 6.2) |
| –CH3 (rha) | 1.10 d (6.2) | 0.91 m | 0.92 d (6.3) | 0.92 d (6.3) | 0.92 d (6.3) | 0.92 d (6.2) | 0.92 d (6.2) |
| –CH2αC O | — | 2.24 td (7.4) | 2.27 td (7.4, 3.2) | 2.27 td (7.3, 3.2) | 2.27 td (7.5, 3.2) | 2.27 t (7.1) | 2.27 t (7.4) |
| –CH2βC O | — | 1.57 sext (7.4) | 1.56 m | 1.55 m | 1.56 m | 1.55 m | 1.59 quint (7.1) |
| –CH2 (FA) | — | — | 1.29 bs | 1.28 bs | 1.28 bs | 1.28 bs | 1.30 bs |
| –CH3 (FA) | — | 0.90 t (6.9) | 0.87 t (6.9) | 0.86 t (6.8) | 0.87 t (6.7) | 0.87 t (6.7) | 0.88 t (6.8) |
| –CH CH– | — | — | — | — | — | — | 5.34 m |
| –CH2αCH | — | — | — | — | — | — | 2.08 bs |