Acetate → Penta-O-galloyl-beta-D-glucose

HRID 467186

Reaction equation

HRID 467186 reaction equation
C1C(O)=C(O)C(O)=CC=1C([O:12][C:13]1[CH:14]=[C:15]([C:21]([O:23][CH2:24][C@H:25]2[O:30][C@@H:29]([O:31][C:32]([C:34]3[CH:35]=[C:36]([OH:53])[C:37]([OH:52])=[C:38]([O:40]C(C4C=C(O)C(O)=C(O)C=4)=O)[CH:39]=3)=[O:33])[C@H:28]([O:54][C:55]([C:57]3[CH:58]=[C:59]([OH:76])[C:60]([OH:75])=[C:61]([O:63]C(C4C=C(O)C(O)=C(O)C=4)=O)[CH:62]=3)=[O:56])[C@@H:27]([O:77][C:78]([C:80]3[CH:81]=[C:82]([OH:99])[C:83]([OH:98])=[C:84]([O:86]C(C4C=C(O)C(O)=C(O)C=4)=O)[CH:85]=3)=[O:79])[C@@H:26]2[O:100][C:101]([C:103]2[CH:104]=[C:105]([OH:122])[C:106]([OH:121])=[C:107]([O:109]C(C3C=C(O)C(O)=C(O)C=3)=O)[CH:108]=2)=[O:102])=[O:22])[CH:16]=[C:17]([OH:20])[C:18]=1[OH:19])=O.C([O-])(=O)C>CO>[C:32]([O:31][C@@H:29]1[O:30][C@H:25]([CH2:24][O:23][C:21](=[O:22])[C:15]2[CH:14]=[C:13]([OH:12])[C:18]([OH:19])=[C:17]([OH:20])[CH:16]=2)[C@@H:26]([O:100][C:101](=[O:102])[C:103]2[CH:108]=[C:107]([OH:109])[C:106]([OH:121])=[C:105]([OH:122])[CH:104]=2)[C@H:27]([O:77][C:78](=[O:79])[C:80]2[CH:85]=[C:84]([OH:86])[C:83]([OH:98])=[C:82]([OH:99])[CH:81]=2)[C@H:28]1[O:54][C:55](=[O:56])[C:57]1[CH:62]=[C:61]([OH:63])[C:60]([OH:75])=[C:59]([OH:76])[CH:58]=1)(=[O:33])[C:34]1[CH:39]=[C:38]([OH:40])[C:37]([OH:52])=[C:36]([OH:53])[CH:35]=1

Participants

4

Reactant 2

HCID 175AcetateHCID 16129778Tannic Acid

Product 1

HCID 65238Penta-O-galloyl-beta-D-glucoseYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1 g of tannic acid according to Japanese Pharmacopoeia (available from Iwaki Seiyaku Co., Ltd.), there were added 50 ml of methanol and 25 ml of acetate buffer (pH 5.5) and the resultant mixture was stirred at 50° C. for 18 hours. After distilling off methanol under a reduced pressure, the residue was extracted three times with ethyl acetate and then the solvent was distilled off under a reduced pressure. This crude product was fractionated by HPLC (YMC-PACK, D-ODS-5 20×250 mm; eluent=methanol: tetrahydrofuran: phosphate buffer (pH 4.5)=3:1:7) to obtain 282 mg of 1,2,3,4,6-penta-O-galloyl-β-D-glucose.

Workup

  1. distillationAfter distilling off methanol under a reduced pressure
  2. extractionthe residue was extracted three times with ethyl acetate
  3. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-680b998af7df428593559b27c77e324e
Source dataset
uspto-grants-1992_10
Patent number
US05159069

Linked notes

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