Gossypol

Gossypol (/ˈɡɒsəpɒl/) is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties.

Not to be confused with Gossypetin.
Gossypol
Names
Preferred IUPAC name
1,1′,6,6′,7,7′-Hexahydroxy-3,3′-dimethyl-5,5′-di(propan-2-yl)[2,2′-binaphthalene]-8,8′-dicarbaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.164.654
KEGG
UNII
  • 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 Y
    Key: QBKSWRVVCFFDOT-UHFFFAOYSA-N Y
  • InChI=1/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
    Key: QBKSWRVVCFFDOT-UHFFFAOYAH
  • CC(C)c1c(O)c(O)c(C=O)c2c1cc(C)c(c2O)-c(c3O)c(C)cc4c3c(C=O)c(O)c(O)c4C(C)C
Properties
C30H30O8
Molar mass 518.562 g·mol−1
Appearance Brown solid
Density 1.4 g/mL
Melting point 177 to 182 °C (351 to 360 °F; 450 to 455 K) (decomposes)
Boiling point 707 °C (1,305 °F; 980 K)
Hazards
GHS labelling:
Warning
H351
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Among other applications, it has been tested as a male oral contraceptive in China. In addition to its putative contraceptive properties, gossypol has also long been known to possess antimalarial properties.

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