Naringin → Naringin

HRID 371752Notes

Reaction equation

HRID 371752 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[CH:17]=[C:18]([OH:34])[C:19]4[C:25](=[O:26])[CH2:24][C@@H:23]([C:27]5[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=5)[O:22][C:20]=4[CH:21]=3)[O:13][C@H:12]([CH2:35][OH:36])[C@@H:11]([OH:37])[C@@H:10]2[OH:38])[C@H:5]([OH:39])[C@H:4]([OH:40])[C@H:3]1[OH:41]>[OH-].[K+].[Pd].O>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[CH:21]=[C:20]([OH:22])[C:19]([C:25]([CH2:24][CH2:23][C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)=[O:26])=[C:18]([OH:34])[CH:17]=3)[O:13][C@H:12]([CH2:35][OH:36])[C@@H:11]([OH:37])[C@@H:10]2[OH:38])[C@H:5]([OH:39])[C@H:4]([OH:40])[C@H:3]1[OH:41].[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[CH:17]=[C:18]([OH:34])[C:19]4[C:25](=[O:26])[CH2:24][C@@H:23]([C:27]5[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=5)[O:22][C:20]=4[CH:21]=3)[O:13][C@H:12]([CH2:35][OH:36])[C@@H:11]([OH:37])[C@@H:10]2[OH:38])[C@H:5]([OH:39])[C@H:4]([OH:40])[C@H:3]1[OH:41]

Participants

6

Reactant 1

HCID 442428Naringin

Product 2

HCID 442428NaringinHCID 9894584Naringin dihydrochalcone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

Five grams of naringin are dissolved in 25 ml of a 10% aqueous solution of potassium hydroxide and hydrogenated at room temperature and at atmospheric pressure, using 500 mg palladium black as catalyst. The resultant colorless solution is diluted with water; after removal of the catalyst the solution is passed through an Amberlite 200 (Rohm & Haas) column, and the alkaline-free eluate is evaporated to dryness. White crystals of the dihydrochalcone of naringin are obtained, m.p. 169°-170° C, in a yield of 98%.

Workup

  1. customafter removal of the catalyst the solution
  2. customthe alkaline-free eluate is evaporated to dryness

Sources & evidence

ORD record
ord-666b5581a16b469689a3063bbdb414cb
Source dataset
uspto-grants-1978_05
Patent number
US04087558

Reaction notes

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