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44449103215
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Physical Data of, )-Denticulaflavonol (1, α] D22 +15.0 (c 0.10, CHCl3, IR (film, 3392, 2921, 2850, 1648, 1609, 1463, 1367, 1261, 1178, 1090 cm-1. 1H NMR (700 MHz, CDCl3, δ, 12.10 (1 H, s, 5-OH, 8.12 (2 H, d, J, 8.8 Hz, H-2′, H-6′, 6.96 (2 H, d, J, 8.8 Hz, H-3′, H-5′, 6.56 (1 H, s, 3-OH, 6.47 (1 H, s, H-8, 6.16 (1 H, s, 7-OH, 5.27 (1 H, t, J, 7.6 Hz, H-14″, 5.07 (1 H, s, 4′-OH, 4.80 (1 H, s, HA-17″, 4.48 (1 H, s, H B-17″, 3.48 (2 H, d, J, 7.6 Hz, H-15″, 2.35 (1 H, m, HA-7″, 2.19 (1 H, m, HA-12″, 1.90 (1 H, m, HB-7″, 1.87 (1 H, m, HB-12″, 1.84 (3 H, s, H-16″, 1.72 (1 H, m, HA-1″, 1.69 (1 H, m, H A-6″, 1.60 (1 H, m, HA-11″, 1.56 1 H, m, HA
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6Na: 581.2874; found: 581.2903.
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29
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44449169380
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The authors quote [α]D26 -131.8 (c 0.05, CHCl3) for the natural, )-denticulaflavonol.9 Compound 1 has a value of [α]D22 +15.0 (c 0.10, CHCl3) and some derivatives have similar values and the same sign, for instance 16 [α]D22 +13.6 (c 0.14, CHCl3, 17 [α]D22 +14.4 (c 0.09, CHCl3, and 20 [α] D22 +12.0 (c 0.65, CHCl3, so it can be concluded that 1 is the enantiomer of the natural, )-denticulaflavonol. The difference in the values could be attributed to the small amount of the natural compound isolated
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3), so it can be concluded that 1 is the enantiomer of the natural (-)-denticulaflavonol. The difference in the values could be attributed to the small amount of the natural compound isolated.
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30
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44449110610
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Spectroscopic Data of Macarangin (2) IR (film, 3380, 2925, 1650, 1608, 1555, 1513, 1484, 1444, 1371, 1315, 1256, 1181, 1087, 1031 cm -1. 1H NMR (400 MHz, CDCl3, δ, 12.10 (1 H, s, 5-OH, 8.13 (2 H, d, J, 9.0 Hz, H-2′, H-6′, 6.97 (2 H, d, J, 9.0 Hz, H-3′, H-5′, 6.57 (1 H, s, 3-OH, 6.48 (1 H, s, H-8, 6.19 (1 H, s, 7-OH, 5.30 (1 H, t, J, 7.0 Hz, H-2″, 5.11 (1 H, s, 4′-OH, 5.06 (1 H, m, H-7″, 3.49 (2 H, d, J, 7.0 Hz, H-1″, 2.10 (4 H, s, H-5″, H-6″, 1.84 (3 H, s, H-4″, 1.68 (3 H, s, H-10″, 1.60 (3 H, s, H-9″) ppm. 13C NMR (100 MHz, CDCl3, δ, 175.2 (C-4, 161.7 (C-7, 158.0 (C-5, 157.4 (C-4′, 155.0 (C-9, 145.5 (C-2, 140.0 (C-3″, 132.2 (C-3, 132.1 (C-8″, 129.6 (C-2′, C-6′, 123.6 (C-1′, 123.3 (C-7″, 120.9 (C-2″, 115.3 C-3′, C-5′
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6Na: 445.1659; found: 445.1639.
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31
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44449141432
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Spectroscopic Data of Isomacarangin (3) IR (film, 3388, 2918, 1648, 1608, 1561, 1509, 1438, 1374, 1315, 1241, 1176, 1114 cm-1. 1H NMR (400 MHz, CDCl3, δ, 11.74 (1 H, s, 5-OH, 8.12 (2 H, d, J, 8.9 Hz, H-2′, H-6′, 6.98 (2 H, d, J, 8.9 Hz, H-3′, H-5′, 6.61 (1 H, s, 3-OH, 6.32 (1 H, s, H-6, 6.14 (1 H, s, 7-OH, 5.31 (1 H, t, J, 6.9 Hz, H-2″, 5.08 (1 H, s, 4′-OH, 5.04 (1 H, m, H-7″, 3.62 (2 H, d, J, 6.9 Hz, H-1″, 2.09 (4 H, s, H-5″, H-6″, 1.85 (3 H, s, H-4″, 1.65 (3 H, s, H-10″, 1.57 (3 H, s, H-9″) ppm. 13C NMR (100 MHz, CDCl3, δ, 175.5 (C-4, 161.0 (C-7, 159.0 (C-5, 157.4 (C-4′, 153.8 (C-9, 145.4 (C-2, 139.4 (C-3″, 132.2 (C-3, 132.1 (C-8″, 129.9 (C-2′, C-6′, 123.6 (C-1′, C-7″, 121.0 (C-2″, 115.7 (C-3′, C-5′, 105.0 C-8
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6: 421.1616; found: 421.1642.
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