Gallic Acid → Isoquercetin

HRID 83468

Reaction equation

HRID 83468 reaction equation
[CH:1]1[C:6]([C:7]2[O:17][C:16]3[CH:15]=[C:14]([OH:18])[CH:13]=[C:12]([OH:19])[C:11]=3[C:9](=[O:10])[C:8]=2[OH:20])=[CH:5][C:4]([OH:21])=[C:3]([OH:22])[CH:2]=1.[CH3:23][C@@H:24]1[O:29][C@@H:28]([O:30][CH2:31][C@H:32]2[O:37][C@@H:36]([O:38][C:39]3[C:48](=[O:49])[C:47]4[C:46]([OH:50])=[CH:45][C:44]([OH:51])=[CH:43][C:42]=4[O:41][C:40]=3[C:52]3[CH:53]=[CH:54][C:55]([OH:59])=[C:56]([OH:58])[CH:57]=3)[C@H:35]([OH:60])[C@@H:34]([OH:61])[C@@H:33]2[OH:62])[C@H:27]([OH:63])[C@H:26]([OH:64])[C@H:25]1[OH:65].C(O)(=[O:75])C=CC1C=CC=CC=1.C1C=CC(O)=C(/C=C/C(O)=O)C=1.C(O)(=O)C1C=C(O)C(O)=C(O)C=1.C1C=CC(N(NC2C([N+]([O-])=O)=CC([N+]([O-])=O)=CC=2[N+]([O-])=O)C2C=CC=CC=2)=CC=1>>[CH:53]1[C:52]([C:40]2[O:41][C:42]3[C:47](=[C:46]([OH:50])[CH:45]=[C:44]([OH:51])[CH:43]=3)[C:48](=[O:49])[C:39]=2[O:38][C@@H:36]2[O:37][C@H:32]([CH2:31][OH:30])[C@@H:33]([OH:62])[C@H:34]([OH:61])[C@H:35]2[OH:60])=[CH:57][C:56]([OH:58])=[C:55]([OH:59])[CH:54]=1.[CH3:23][C@H:24]1[O:29][C@@H:28]([O:20][C:8]2[C:9](=[O:10])[C:11]3[C:12]([OH:19])=[CH:13][C:14]([OH:18])=[CH:15][C:16]=3[O:17][C:7]=2[C:6]2[CH:1]=[C:2]([OH:75])[C:3]([OH:22])=[C:4]([OH:21])[CH:5]=2)[C@@H:27]([OH:63])[C@@H:26]([OH:64])[C@@H:25]1[OH:65]

Participants

8

Reactant 6

HCID 370Gallic AcidHCID 87842-Propenoic acid, 3-phenyl-HCID 74358Hydrazine, 1,1-diphenyl-2-(2,4,6-trinitrophenyl)-HCID 637540O-Coumaric AcidHCID 5280343QuercetinHCID 5280805Rutin

Product 2

HCID 5280804IsoquercetinHCID 404911935,7-dihydroxy-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Procedure

UV spectra were measured on a Perkin-Elmer Lambda 35 UV/VIS spectrometer. NMR experiments were conducted on a Bruker Avance AV300 NMR spectrometer operating at 300.13 MHz for 1H and 75.48 MHz for 13C using standard Bruker software. Mass spectra were obtained on a ThermoFinnigan LCQ utilizing both ESI and APCI in the positive and negative modes. HRESIMS was performed on a Micromass Q-TOF Ultima mass spectrometer. HPLC was done on a Waters 2695 using a Phenomenex Aqua column (250×4.6 mm, 5 μm) and monitored using a Waters 996 PDA scanning from 240 to 600 nm. Column chromatography was accomplished using Sephadex LH-20 (Pharmacia, 25-100 μm), reversed-phase C18 silica gel (J. T. Baker, 40 μm), and Diaion HP-20 (Mitsubishi, Japan). Separations were monitored using silica gel 60 F254 and RP18 F254 TLC plates (1 mm thickness, EM Science, Germany). Quercetin, rutin, cinnamic acid, O-coumaric acid, gallic acid, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) were purchased from Sigma (MO, USA). Isoquercitrin and myricitrin were previously isolated in the laboratory (23).

Workup

  1. customMass spectra were obtained on a ThermoFinnigan LCQ

Sources & evidence

ORD record
ord-149252e9ce154b5e9ae76bde3686e059
Source dataset
uspto-grants-2014_09
Patent number
US08846757B2

Linked notes

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