1,3,8-Trihydroxy-6-methyl-9(10H)-anthracenone → HCID 178428878, compound

HRID 1034375Notes

Reaction equation

HRID 1034375 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]2[C:9]([C:11]3[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=3[CH2:19][C:4]=2[CH:3]=1)=[O:10]>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]2[C:9](=[O:10])[C:11]3[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[C:13]4[C:12]=3[C:19](=[C:19]3[C:12]5=[C:13]4[C:14]([OH:18])=[CH:15][C:16]([OH:17])=[C:11]5[C:9](=[O:10])[C:5]4[C:6]([OH:8])=[CH:7][C:2]([CH3:1])=[CH:3][C:4]3=4)[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 1226351,3,8-Trihydroxy-6-methyl-9(10H)-anthracenone

Product 1

HCID 178428878HCID 178428878, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Emodin anthrone is dimerized to give the 10,10'-coupled bianthrones by reacting emodin anthrone with ferric chloride (FeCl3) in ethanol, as described in Kinget, R., Planta. Med., vol. 15, pp. 233-39 (1967), which is also incorporated herein by specific reference. This reaction results in two diastereomers, the meso and the dl-pair. These compounds are readily separated on reverse phase high pressure liquid chromatography ("HPLC"). Subsequent oxidation of the bianthrones with oxygen in methanol containing triethylamine produces protohypericin, which is converted into hypericin upon exposure to sunlight. Alternatively air oxidation of the bianthrones in hot ammonium hydroxide and exposure to sunlight give rise to hypericin. The resulting compounds are characterized by HPLC, thin layer chromatography ("TLC"), and ultraviolet/visual spectrometry.

Workup

  1. customThis reaction results in two diastereomers
  2. customThese compounds are readily separated on reverse phase high pressure liquid chromatography ("HPLC")
  3. additionSubsequent oxidation of the bianthrones with oxygen in methanol containing triethylamine

Sources & evidence

ORD record
ord-c321e0aac8f641979ea442e445f4d036
Source dataset
uspto-grants-1994_05
Patent number
US05316768

Reaction notes

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