Gossypol

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
CAS Number	303-45-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL51483 ;
ChemSpider	3383 ;
DrugBank	DB13044;
ECHA InfoCard	100.164.654
IUPHAR/BPS	4204;
KEGG	C07667 ;
PubChem CID	3503;
UNII	KAV15B369O ;
CompTox Dashboard (EPA)	DTXSID5023110 ;
	InChI 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 Key: QBKSWRVVCFFDOT-UHFFFAOYSA-N ; 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;
	SMILES 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
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H351
Precautionary statements	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). verify (what is ?) Infobox references

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.^[1]

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.^[2]

^ Beise, Chase L.; Dowd, Michael K.; Reilly, Peter J. (2005). "Conformational analysis of gossypol and its derivatives by molecular mechanics". Journal of Molecular Structure: THEOCHEM. 730 (1–3): 51–58. doi:10.1016/j.theochem.2005.05.010.
^ Dodou, Kalliopi (2005-10-28). "Investigations on gossypol: past and present developments". Expert Opinion on Investigational Drugs. 14 (11): 1419–1434. doi:10.1517/13543784.14.11.1419. ISSN 1354-3784. PMID 16255680. S2CID 32120983.

[1] Beise, Chase L.; Dowd, Michael K.; Reilly, Peter J. (2005). "Conformational analysis of gossypol and its derivatives by molecular mechanics". Journal of Molecular Structure: THEOCHEM. 730 (1–3): 51–58. doi:10.1016/j.theochem.2005.05.010.

[2] Dodou, Kalliopi (2005-10-28). "Investigations on gossypol: past and present developments". Expert Opinion on Investigational Drugs. 14 (11): 1419–1434. doi:10.1517/13543784.14.11.1419. ISSN 1354-3784. PMID 16255680. S2CID 32120983.

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