Physiochemical Properties of Gossypol

Gossypol was first discovered and isolated as a crude pigment by Longmore (1886) from cottonseed oil foot, a mixture of precipitated soaps and gums produced in the refining of crude cottonseed oil with 

FIGURE 6.2 (A) Atropisomers of gossypol and (B) formation of naphthalene ring in 

Gossypol is chemically reactive due to the reactivity of carbonyl and phenolic hydroxyl groups as well as its bulky binaphthalene structure. Gossypol can react with other compounds to form bound gossypol (BG). In order to better describe the chemical status (forms) of gossypol in cottonseed products, three terms (i.e., FG, BG, and TG) are frequently used. Based on the AOCS (American Oil Chemists Society) official 

FIGURE 6.3 Tautomeric forms of gossypol (A) aldehyde, (B) ketol, and (C) hemiacetal. 

Gossypol Gossypol schiff base Secondary amine 

---