A natural polyphenol with diverse effects
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Isomer(s)
42421(−)-Gossypol (acetate)
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Gossypol

Item No. 14482

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1’,6,6’,7,7’-hexahydroxy-3,3’-dimethyl-5,5’-bis(1-methylethyl)-[2,2’-binaphthalene]-8,8’-dicarboxaldehyde
CAS Number
303-45-7
Synonyms
  • BL 193
  • (±)-Gossypol
  • NSC 56817
  • NSC 624336
  • Pogosin
Molecular Formula
C30H30O8
Formula Weight
518.6
Purity
≥85%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 15 mg/mlEthanol: 10 mg/ml
λmax
236, 290, 372 nm
SMILES
OC1=C(O)C(C(C)C)=C(C=C(C)C(C2=C(O)C(C(C([H])=O)=C(O)C(O)=C3C(C)C)=C3C=C2C)=C4O)C4=C1C([H])=O
InChi Code
InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
InChi Key
QBKSWRVVCFFDOT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Gossypol is a racemic mixture of natural polyphenols isolated from parts of the cotton plant (genus Gossypium). It causes infertility in a variety of cotton pests and spermatogenesis arrest in humans.1 Gossypol also has antimalarial properties, preventing the growth of P. falciparum at low micromolar concentrations.2 It inhibits aldose reductase (Ki = 0.5 µM).3 Gossypol also acts as an anticancer agent, inhibiting cell growth in various cancer cell lines, in part by blocking the anti-apoptotic functions of Bcl-2 and Bcl-xL, again at low micromolar concentrations.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Coutinho, E.M. Gossypol: A contraceptive for men. Contraception 65(4), 259-263 (2002).

    2. Royer, R.E., Deck, L.M., Campos, N.M., et al. Biologically active derivatives of gossypol: Synthesis and antimalarial activities of peri-acylated gossylic nitriles. J. Med. Chem. 29(9), 1799-1801 (1986).

    3. Deck, L.M., Vander Jagt, D.L., and Royer, R.E. Gossypol and derivatives: A new class of aldose reductase inhibitors. J. Med. Chem. 34(11), 3301-3305 (1991).

    4. Yan, F., Cao, X.X., Jiang, H.X., et al. A novel water-soluble gossypol derivative increases chemotherapeutic sensitivity and promotes growth inhibition in colon cancer. J. Med. Chem. 53(15), 5502-5510 (2010).