Genistin → Genistein

HRID 1489847Notes

Reaction equation

HRID 1489847 reaction equation
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[CH:13][C:12]([O:19][C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:31])[CH:2]=1>Cl>[CH:5]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[CH:13][C:12]([OH:19])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:1][CH:2]=[C:3]([OH:31])[CH:4]=1

Participants

3

Reactant 1

HCID 5281377Genistin

Product 1

HCID 5280961GenisteinYield 96.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

About 1578 mg of genistin were refluxed in 960 ml 4N HCl for five hours at 100°±5° C. About 948 mg genistein were obtained with about 96% recovery. 483.2 mg of genistein (99% purity) recovered from the hydrolysis step was dissolved in 450 ml methanol and crystallized in 20 ml methanol. About 373.8 mg of genistein crystal was obtained giving a 77% recovery and 99.5% purity. Genistein m.p. 298.4°-299.9° C. 1H NMR (400 MHz, DMSO-d6) 6.22 (1H, d, J=2 Hz, H-8), 6.38 (1H, d, J=2 Hz, H-6), 6.83 (2H, d, J=8 Hz, H-3'), 7.39 (2H, d, J=8 Hz, H-2'), 8.43 (1H, s, H-2), 9.61 (1H, s, 4'-OH), 10.90 (1H, s, 7-OH) 12.92 (1H, s, 5-OH). 13C NMR (100 MHz, DMSO-d6) 154.5, 122.8, 180.7, 162.5, 99.5, 164.8, 94.2, 157.9, 105.0, 121.7, 130.7, 115.6, 158.1.

Sources & evidence

ORD record
ord-e2162a87be714cc0964ff6baa90cb94d
Source dataset
uspto-grants-1997_10
Patent number
US05679806

Reaction notes

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