Epigallocatechin Gallate → Hesperidin

HRID 1525143Notes

Reaction equation

HRID 1525143 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][CH2:9][C@H:10]2[O:15][C@@H:14]([O:16][C:17]3[CH:27]=[C:26]4[C:20]([C:21]([CH2:23][C@@H:24]([C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=5)[O:25]4)=[O:22])=[C:19]([OH:38])[CH:18]=3)[C@@H:13]([OH:39])[C@@H:12]([OH:40])[C@@H:11]2[OH:41])[C@H:5]([OH:42])[C@H:4]([OH:43])[C@H:3]1[OH:44].C1C2C(=CC(O)=CC=2O)O[C@H](C2C=C(O)C(O)=C(O)C=2)[C@@H]1OC(C1C=C(O)C(O)=C(O)C=1)=O>>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][CH2:9][C@H:10]2[O:15][C@@H:14]([O:16][C:17]3[CH:18]=[C:19]([OH:38])[C:20]4[C:21](=[O:22])[CH2:23][C@@H:24]([C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([OH:36])[CH:29]=5)[O:25][C:26]=4[CH:27]=3)[C@H:13]([OH:39])[C@@H:12]([OH:40])[C@@H:11]2[OH:41])[C@H:5]([OH:42])[C@H:4]([OH:43])[C@H:3]1[OH:44].[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][CH2:9][C@H:10]2[O:15][C@@H:14]([O:16][C:17]3[CH:27]=[C:26]4[C:20]([C:21]([CH2:23][C@@H:24]([C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=5)[O:25]4)=[O:22])=[C:19]([OH:38])[CH:18]=3)[C@@H:13]([OH:39])[C@@H:12]([OH:40])[C@@H:11]2[OH:41])[C@H:5]([OH:42])[C@H:4]([OH:43])[C@H:3]1[OH:44]

Participants

4

Reactant 2

HCID 65064Epigallocatechin GallateHCID 3035218(2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-one2×

Product 2

HCID 10621HesperidinHCID 3035218(2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-one

Procedure

A hesperidin composition was obtained as a hesperidin-containing aqueous solution by a same procedure as in Example 1, except that a methylhesperidin preparation (manufactured by Hamari Chemicals Ltd., methylhesperidin content 100%, the same shall apply hereafter) was used instead of the EGCG preparation. Reaction conditions and the measurement result of a concentration of hesperidin and methylhesperidin in the composition are shown in Table 1.

Workup

  1. additioncontaining aqueous solution by a same procedure as in Example 1
  2. customReaction conditions

Sources & evidence

ORD record
ord-e800ded5b7514afcbd1973e8261151bb
Source dataset
uspto-grants-2015_07
Patent number
US09079933B2

Reaction notes

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