Gossypol hexaacetate → Gossypol

HRID 848712Notes

Reaction equation

HRID 848712 reaction equation
[CH3:1][C:2]1[C:24]([C:25]2[C:26]([CH3:52])=[CH:27][C:28]3[C:38]([CH:39]([CH3:41])[CH3:40])=[C:37]([O:42]C(C)=O)[C:36]([O:46]C(C)=O)=[C:35]([CH:50]=[O:51])[C:29]=3[C:30]=2[O:31]C(C)=O)=[C:23]([O:53]C(C)=O)[C:5]2=[C:6]([CH:21]=[O:22])[C:7]([O:17]C(C)=O)=[C:8]([O:13]C(C)=O)[C:9]([CH:10]([CH3:12])[CH3:11])=[C:4]2[CH:3]=1.S(=O)(O)[O-].[Na+]>>[CH3:52][C:26]1[C:25]([C:24]2[C:2]([CH3:1])=[CH:3][C:4]3[C:9]([CH:10]([CH3:12])[CH3:11])=[C:8]([OH:13])[C:7]([OH:17])=[C:6]([CH:21]=[O:22])[C:5]=3[C:23]=2[OH:53])=[C:30]([OH:31])[C:29]2=[C:35]([CH:50]=[O:51])[C:36]([OH:46])=[C:37]([OH:42])[C:38]([CH:39]([CH3:40])[CH3:41])=[C:28]2[CH:27]=1

Participants

3

Reactant 2

HCID 35450Gossypol hexaacetateHCID 23665763Sodium Bisulfite

Product 1

HCID 3503Gossypol

Conditions

Temperature
50 °C

Procedure

Gossypol acetic acid was obtained from the U.S. Department of Agriculture. Analytically pure gossypol was prepared from the acetic acid adduct by the method of Campbell et al., J. Amer. Chem. Soc. 59, 1723-38(1937). In the process, the adduct is dissolved in peroxide-free ether, mixed with aqueous sodium bisulfite solution (0.4%) and heated at 50° C. The resultant solid is further purified by repeating the process and by crystallization of the final solid from a mixture of ether and petroleum ether.

Workup

  1. customThe resultant solid is further purified
  2. customby crystallization of the final solid
  3. additionfrom a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-3559febda351455d83a10a3756193b51
Source dataset
uspto-grants-1981_10
Patent number
US04297341

Reaction notes

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