Ammonium Hydroxide → Gossypol

HRID 1157112Notes

Reaction equation

HRID 1157112 reaction equation
[NH4+].[OH-:2].[CH3:3][C:4]1[CH:9]=[C:8]2[C:10]([CH:24]([CH3:26])[CH3:25])=[C:11]([OH:23])[C:12](/[C:14](=[CH:15]\NC3C=CC=CC=3)/[C:7]2=[C:6]([OH:27])[C:5]=1[C:28]1[C:33]([OH:34])=[C:32]2[C:35]([CH:44]=[O:45])=[C:36]([OH:43])[C:37]([OH:42])=[C:38]([CH:39]([CH3:41])[CH3:40])[C:31]2=[CH:30][C:29]=1[CH3:46])=[O:13]>CO>[CH3:3][C:4]1[C:5]([C:28]2[C:29]([CH3:46])=[CH:30][C:31]3[C:38]([CH:39]([CH3:41])[CH3:40])=[C:37]([OH:42])[C:36]([OH:43])=[C:35]([CH:44]=[O:45])[C:32]=3[C:33]=2[OH:34])=[C:6]([OH:27])[C:7]2=[C:14]([CH:15]=[O:2])[C:12]([OH:13])=[C:11]([OH:23])[C:10]([CH:24]([CH3:26])[CH3:25])=[C:8]2[CH:9]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178422106HCID 178422106, compound

Product 1

HCID 3503Gossypol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mass spectrometer was a Micromass Quattro Ultima LC/MS/MS detector by Waters, and contained a triple quadrupole mass spectrometer with negative electrospray ionization. Because the HPLC did not provide the correct ionization matrix for negative electrospray ionization of the dianilino-gossypol, 0.6% NH4OH in methanol was introduced past the HPLC column at a flow rate of 0.05 mL/minute. Post-column mixing of the NH4OH in MeOH with the HPLC eluant was achieved using a mixing T-connection. In MS/MS mode, the first quadrupole was used to select 667.3 as the mass to charge ratio that represented the negative ion of dianilino-gossypol. In the second quadrupole, the 667.3 mass to charge ratio was fragmented in a collision cell. The third quadrupole was used to select the fragment ion, monoanilino-gossypol, which had a mass to charge ratio of 574.2 as a result of the loss of an aniline. Detection of the second fragment ion provides improved specificity and increased signal to noise ratios.

Workup

  1. additionwas introduced past the HPLC column at a flow rate of 0.05 mL/minute
  2. additionto charge ratio that
  3. additionIn the second quadrupole, the 667.3 mass to charge ratio

Sources & evidence

ORD record
ord-8ce4e681abf045249b35de3f2a3d0ccb
Source dataset
uspto-grants-2010_10
Patent number
US07807469B2

Reaction notes

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