Gossypol
Title: Gossypol
CAS Registry Number: 303-45-7
CAS Name: 1,1¢,6,6¢,7,7¢-Hexahydroxy-3,3¢-dimethyl-5,5¢-bis(1-methylethyl)[2,2¢-binaphthalene]-8,8¢-dicarboxaldehyde
Additional Names: 2,2¢-bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene]; 2,2¢-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]
Molecular Formula: C30H30O8
Molecular Weight: 518.55
Percent Composition: C 69.49%, H 5.83%, O 24.68%
Literature References: Yellow pigment found in cottonseed; functions as a natural insecticide in plants. Name derived from the botanical name of the cotton plant, Gossypium L., Malvaceae. Isoln: J. Longmore, J. Soc. Chem. Ind. 5, 200 (1886); L. Marchlewski, J. Prakt. Chem. 60, 84 (1899); K. N. Campbell et al., J. Am. Chem. Soc. 59, 1723 (1937). Structural studies: R. Adams et al., ibid. 60, 2193 (1938). Synthesis: Edwards, J. Am. Oil Chem. Soc. 47, 441 (1970). NMR studies: J. W. Jaroszewski et al., NMR Spectrosc. Drug Res. 26, 75 (1988). Vibrational CD structural studies: T. B. Freedman et al., Chirality 15, 196 (2003). Prepn of enantiomers: M. K. Dowd, ibid. 486. HPLC determn: G. B. Marcelle et al., J. Pharm. Sci. 73, 396 (1984). Metabolism studies: M. B. Abou-Donia et al., Lipids 5, 938 (1970). Mechanism of action study: C.-Y. G. Lee et al., Mol. Cell. Biochem. 47, 65 (1982). Structure-activity study in tumor cell lines: M. D. Shelley et al., Anti-Cancer Drugs 11, 209 (2000). Clinical evaluation in malignant glioma: P. Bushunow et al., J. Neuro-Oncol. 43, 79 (1999); in male contraception: E. M. Coutinho et al., Contraception 61, 61 (2000). Review of chemistry: R. Adams et al., Chem. Rev. 60, 555-574 (1960); of toxicity in livestock: S. E. Morgan, Vet. Clinics North Am.: Food Anim. Pract. 5, 251-262 (1989); of clinical pharmacology and use as a male contraceptive agent: D. Wu, Drugs 38, 333-341 (1989); E. M. Coutinho, Contraception 65, 259-263 (2002).
Properties: Exists in 3 tautomeric forms. Yellow crystals from ether, mp 184°; from chloroform, mp 199°; from ligroin, mp 214°. Light sensitive. Very sol in methanol, ethanol, cold dioxane, diethylene glycol, ether, ethyl acetate, acetone, carbon tetrachloride, pyridine, chloroform, DMF, lipids. Freely sol (with slow decompn) in dil aq solns of ammonia and sodium carbonate. Slightly sol in glycerol, cyclohexane. Insol in water. Absorption max: 385 nm (e 18000).
Melting point: mp 184°; mp 199°; mp 214°
Absorption maximum: Absorption max: 385 nm (e 18000)
 
Derivative Type: R-Form
CAS Registry Number: 90141-22-3
Additional Names: (-)-gossypol
Properties: Bright yellow crystals from acetone, mp 181-184° (dec). [a]D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3) (Dowd).
Melting point: mp 181-184°
Optical Rotation: [a]D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3)
 
Derivative Type: S-Form
CAS Registry Number: 20300-26-9
Additional Names: (+)-gossypol
Literature References: Isoln from Thespesia populnea: T. J. King, L. B. de Silva, Tetrahedron Lett. 9, 261 (1968); S. C. Datta et al., Indian J. Chem. 10, 263 (1972). Synthesis: A. I. Meyers, J. J. Willemsen, Tetrahedron 54, 10493 (1998).
Properties: Bright yellow crystals from acetone, mp 181-184° (dec). [a]D28 +386 to +390° (c = 0.5 g/100 g soln in CHCl3) (Dowd). uv max (ethanol): 237.5, 277. 378 nm (log e 4.8, 4.4, 4.2) (Datta).
Melting point: mp 181-184°
Optical Rotation: [a]D28 +386 to +390° (c = 0.5 g/100 g soln in CHCl3)
Absorption maximum: uv max (ethanol): 237.5, 277. 378 nm (log e 4.8, 4.4, 4.2) (Datta).
 
Derivative Type: Gossypol Acetic Acid
CAS Registry Number: 12542-36-8
Properties: Bright yellow plates, mp 187° (Adams et al.).
Melting point: mp 187°
 
CAUTION: Potentially toxic to animals overfed cottonseed products; symptoms of overexposure may include cardiac failure, shortness of breath, pulmonary edema, and reproductive effects (Morgan).

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